     
1982

- Apr Madonna is signed to her first recording contract with Warner Bros/Sire Records.
- Oct "Everybody" is released as a 12-inch single in US. (A video for "Everybody" is made on a $1,500 budget, directed by Ed Steinberg and features Madonna at The Paradise Garage club in New York, NY but will not be released on MTV).
- Dec (25) "Everybody" hits US #107.
     
1983

- Jan (8) "Everybody" hits #3 on US Hot Dance Music/Club Play chart and fails to enter the Hot 100 singles chart.
- Mar "Burning Up/Physical Attraction" is released as a 12-inch single in US.
- May Madonna performs "Holiday" at Studio 54, Manhattan, NY.
- (21) "Burning Up/Physical Attraction" hits #3 on US Hot Dance Music/Club Play chart and fails to enter the Hot 100 singles chart.
- Jun Madonna performs "Holiday" at the Music Machine, London, England.
- Jul "Holiday" single is released. (A low budget video for "Holiday" is made but will never be commercially released).
- (27) Madonna LP is released.
- Sep (24) Madonna performs "Physical Attraction", "Everybody", "Holiday" and "Burning Up" at Uncle Sam's Club, Levittown, NY. "Holiday" hits #1 on US Hot Dance Music/Club Play Chart - it is her first No. 1 single on the dance charts.
- Oct "Burning Up" video premieres on MTV.
- (13) Madonna performs "Burning Up", "Everybody" and "Holiday" at Camden Palace's Thursday Party Night, London, England.
- (29) "Holiday" enters the Hot 100 US singles chart at #76.
- Nov Madonna films a cameo appearance as a nightclub singer for Harold Becker movie Vision Quest.
    
1984

- Jan (14) Madonna performs "Holiday" on ABC-TV's American Bandstand (hosted by Dick Clark).
- (26) Madonna performs "Holiday" on BBC1-TV's Top Of The Pops in London, England during a promotional visit in UK and is also interviewed by Number One, The Face and Record Mirror magazines.
- (28) "Holiday" hits US #16.
- Feb Madonna performs on Channel 4 TV's The Tube in London, England. "Borderline" video premieres on MTV.
- (15) "Borderline" single is released.
- Apr Madonna begins recording sessions for her new Like A Virgin LP.
- May (31) Madonna is certified gold (500,000 units).
- Jun (16) "Borderline" hits US #10.
- Aug "Lucky Star" single and video are released.
- (14) Madonna is certified 1x platinum (1 million units).
- Sep Madonna begins filming Desperately Seeking Susan, starring Rosanna Arquette and directed by Susan Seidelman.
- (14) Madonna performs "Like A Virgin" and is nominated for Best New Artist Video ("Borderline") at the 1st annual MTV Video Music Awards at Radio City Music Hall, New York, NY.
- Oct (20) Madonna hits US #8 and "Lucky Star" hits US #4.
- Nov (7) Madonna is guest of honor at a party at the club Private Eyes, New York, NY to celebrate the release of Like A Virgin.
- (12) Like A Virgin LP is released.
- (13) "Like A Virgin" video premieres on MTV.
- (17) "Like A Virgin" single is released.
- Dec (3) "Madonna" (a 4-videoclip collection: "Burning Up", "Borderline", "Lucky Star", "Like A Virgin") is released on home video.
- (5) Madonna is certified 2x platinum (2 million units).
- (13) Madonna performs "Like A Virgin" on BBC1-TV's Top Of The Pops in London, England during a promotional visit in UK.
- (22) "Like A Virgin" hits US #1 for six weeks - it is her first US No. 1 hit single.
    
1985

- Jan (10) Madonna begins filming "Material Girl" video in Los Angeles, CA, directed by Mary Lambert and meets 24-year-old actor Sean Penn on the set. "Like A Virgin" single is certified gold (1 million units).
- (23) Like A Virgin is certified 2x platinum (2 million units).
- (28) Madonna presents an award to Prince & The Revolution and is nominated for Favorite Pop/Rock Female Artist at the 12th annual American Music Awards at the Shrine Auditorium, Los Angeles, CA.
- Feb "Material Girl" single and video are released.
- (5) Like A Virgin is certified 3x platinum (3 million units).
- (9) Like A Virgin hits US #1 for 3 weeks.
- (13) Madonna and Sean Penn have their first date at the club Private Eyes, New York, NY.
- (15) Vision Quest is released. "Crazy For You" and "Gambler" videos (clips from Vision Quest) premiere on MTV.
- Mar "Crazy For You" single (from Vision Quest) is released. Madonna begins rehearsals for "The Virgin Tour" in Los Angeles, CA.
- (23) "Material Girl" hits US #2.
- (29) Desperately Seeking Susan is released. "Into The Groove" video (from Desperately Seeking Susan) premieres on MTV.
- Apr "Angel/Into The Groove" is released as a 12-inch single.
- (10,12,13) "The Virgin Tour" opens with 3 sold-out concerts at the Paramount Theatre, Seattle, WA.
- (15,16) Madonna performs at the Arlene Schnitzer Concert Hall, Portland, OR.
- (19,20) Madonna performs at the Open Air Theatre, San Diego, CA.
- (21) Madonna performs at the Pacific Amphitheatre, Costa Mesa, CA.
- (23) Madonna performs at the Civic Auditorium, San Francisco, CA. Like A Virgin is certified 4x platinum (4 million units).
- (26,27,28) Madonna performs 3 sold-out concerts at the Universal Amphitheatre, Los Angeles, CA.
- (30) Madonna performs at ASU Activity Centre, Tempe, AZ.
- May (3) Madonna performs at the Convention Centre, Dallas, TX.
- (4) Madonna performs at The Summit, Houston, TX.
- (5) Madonna performs at the Frank Erwin Centre, Austin, TX.
- (7) Madonna performs at UNO Lakefront Arena, New Orleans, LA.
- (9) Madonna performs at the Sun Dome, Tampa, FL.
- (10) Madonna performs at the Orange County Civic Centre, Orlando, FL.
- (11) Madonna performs at the Hollywood Sportatorium, Miami, FL. "Crazy For You" hits US #1.
- (14) Madonna performs at The Omni, Atlanta, GA.
- (16) Madonna performs at Public Hall, Cleveland, OH.
- (17) Madonna performs at the Cincinnati Gardens, Cincinnati, OH.
- (18,20) Madonna performs 2 sold-out concerts at the UIC Pavilion, Chicago, IL.
- (21) Madonna performs at St. Paul Civic Centre, St. Paul, MN.
- (23) Madonna performs at Maple Leaf Gardens, Toronto, ON, Canada.
- (25,26) Madonna performs at Cobo Hall, Detroit, MI.
- (25) "Madonna" hits US #1 on Top Music Videos chart.
- (28) Madonna performs at the Civic Arena, Pittsburgh, PA.
- (29) Madonna performs at The Spectrum, Philadelphia, PA.
- (30) Madonna performs at the Hampton Coliseum, Hampton, VA.
- (31) "Madonna" video is certified 1x platinum (50,000 units).
- Jun (1) Madonna performs at the Merriweather Post Pavilion, Columbia, MD.
- (2) Madonna performs at The Centrum, Worcester, MA.
- (3) Madonna performs at New Haven Coliseum, New Haven, CT.
- (6,7,8) Madonna performs 3 sold-out concerts at Radio City Music Hall, New York, NY.
- (10,11) "The Virgin Tour" ends with 2 sold-out concerts at Madison Square Garden, New York, NY.
- (24) Madonna and Sean Penn announce they will marry on Aug 16, 1985.
- (29) "Angel/Into The Groove" hits US #5.
- Jul "Into The Groove" (from Desperately Seeking Susan) is released as a UK single. "Holiday" is re-released as a UK single.
- (7) Penthouse magazine announces it will publish nude photographs of Madonna taken in 1979 during her early years.
- (8) Playboy magazine also announces it will also publish nude photographs of Madonna.
- (10) The Playboy magazine issue of nude Madonna photos is released.
- (13) Madonna performs "Into The Groove", "Holiday", "Love Makes The World Go Round" and joins The Thompson Twins for a rendition of The Beatles' "Revolution" at the Live Aid benefit concert at JFK Stadium, Philadelphia, PA.
- (16) "Crazy For You" single is certified gold (1 million units). The Penthouse magazine issue of nude Madonna photos is released.
- (22) Like A Virgin is certified 5x platinum - the first solo album by a female artist to be certified for sales of 5 million copies.
- (30) "Angel/Into The Groove" 12-inch single is certified gold (500,000 units).
- Aug "Dress You Up" single and video are released.
- (2) Madonna loses a court battle against director Stephen Jon Lewicki over the video release of A Certain Sacrifice, a soft-porn movie Madonna filmed between 1979-81 during her early years.
- (3) "Into The Groove" hits UK #1 and "Holiday" hits UK #2 - Madonna is the only female artist ever to occupy the top 2 positions simultaneously on the UK charts.
- (16) Madonna and Sean Penn are married on her 27th birthday on a clifftop in Malibu, CA with Cher, Martin Sheen, Rob Lowe, Carrie Fisher, Diane Keaton, David Letterman, Rosanna Arquette, Christopher Walken, Steve Rubell and others in attendance, and will honeymoon at the Highlands Inn, Carmel, CA; after the honeymoon, Madonna begins work on a new album.
- Oct "Gambler" (from Vision Quest) is released as a UK single and hits #4.
- (1) A Certain Sacrifice is released on home video, priced at $59.95.
- (5) "Dress You Up" hits US #5.
- (6) Madonna and Rosanna Arquette participate in an all-star Pro-Peace Rally in Van Nuys, CA.
- (15) Madonna is certified 3x platinum (3 million units).
- Nov (6) Like A Virgin is certified 6x platinum (6 million units).
- (9) Madonna hosts the 1985-86 season premiere of NBC-TV's Saturday Night Live.
- (11) "Madonna Live: The Virgin Tour" is released on home video.
- Dec (3) "Madonna Live: The Virgin Tour" video is certified 1x platinum (100,000 units).
- (14) "Dress You Up" hits UK #5 - it is her eighth UK Top 10 hit of 1985 and becomes the only female artist in 30 years to have 3 records in the UK Top 15 charts.
- (21) Madonna wins 7 Billboard Music Awards: Top Pop Artist, Top Pop Album Artist - Female, Top Pop Singles Artist, Top Pop Singles Artist - Female, Top Dance Club Play Artist, Top Dance Sales Artist and Top Music Video ("Madonna").
    
1986

- Jan "Borderline" is re-released as a UK single. Madonna and Sean begin filming Shanghai Surprise in Macau, China, directed by Jim Goddard and produced by ex-Beatle George Harrison's Handmade Films company.
- (18) "Madonna Live: The Virgin Tour" hits US #1 on Top Music Videos chart.
- Feb (15) "Borderline" hits UK #2.
- (20) Madonna and Sean attend the premiere of his film At Close Range at the Berlin Film Festival, Berlin, Germany.
- (21) Madonna and Sean arrive in London, England to complete filming on Shanghai Surprise; upon their arrival at Heathrow Airport, a photographer is knocked down by their limousine and they are later nicknamed "The Poison Penns" by the British press.
- (27) Madonna wins Worst-Dressed Female Artist in Rolling Stone magazine's 10th annual Readers Poll.
- Mar (6) Madonna and George Harrison hold a press conference at Kensington Roof Gardens, London, England to discuss the filming of Shanghai Surprise; when asked by a reporter to apologize for her and Sean's behavior towards the British press, Madonna answers: "I have nothing to apologize for".
- (11) Madonna is named Favorite Female Musical Performer at the 12th annual People's Choice Awards: she accepts her award on the set of Shanghai Surprise in London, England.
- Apr "Live To Tell" single and video (theme from film At Close Range) are released.
- (16) Madonna and Sean attend the Los Angeles premiere of his film At Close Range at the Bruin Theatre.
- May (31) "Live To Tell" hits #1 for 3 weeks on US Hot Adult Contemporary singles chart.
- Jun (7) "Live To Tell" hits US #1.
- (18) "Papa Don't Preach" single is released. (The song's lyrics about a teenage pregnant girl's decision to keep her baby causes a controversy with US organization Planned Parenthood).
- (30) True Blue LP is released. "Papa Don't Preach" video premieres on MTV.
- Jul Madonna and Sean begin rehearsals for a Lincoln Centre Theatre workshop production of David Rabe's play Goose & Tom-Tom, directed by Gregory Mosher which will be performed to a non-public audience for only 4 nights.
- Aug (16) Madonna and Sean celebrate her 28th birthday and their first wedding anniversary at Gotham Bar and Grill, New York. True Blue hits US #1 for 5 weeks and "Papa Don't Preach" hits US #1 for 2 weeks.
- (28) Madonna and Sean open in Goose & Tom-Tom at Lincoln Centre's Mitzi Newhouse Theatre, New York, NY.
- (29) Shanghai Surprise premieres at 400 US theatres.
- (31) Madonna and Sean play their final performance in Goose & Tom-Tom.
- Sep (5) Madonna is honored with the Video Vanguard Award for her visionary videos at the 3rd annual MTV Video Music Awards at the Palladium, New York, NY and at the Universal Amphitheatre, Los Angeles, CA.
- (8) True Blue is certified 2x platinum (2 million units).
- (10) "True Blue" single is released.
- (19) Shanghai Surprise is released nationwide. Madonna attends the 2nd annual Commitment To Life benefit for AIDS Project Los Angeles (APLA) to honor Elizabeth Taylor at the Wiltern Theatre, Los Angeles, CA.
- Oct (2) "True Blue" video (non-US version) premieres on BBC1-TV's Top Of The Pops.
- (11) Madonna makes a surprise appearance on the season premiere of NBC-TV's Saturday Night Live.
- Nov Madonna begins filming Who's That Girl, co-starring Griffin Dunne and Sir John Mills, directed by James Foley.
- (10) Madonna participates in an all-star AIDS benefit modelling fashion show at Barney's clothes store, New York, NY, which benefits the AIDS Research Clinic at St. Vincent's Hospital in Manhattan, NY.
- (15) "True Blue" hits US #3. (18) True Blue is certified 3x platinum (3 million units).
- Dec "Open Your Heart" single and video are released. Madonna wins a Billboard Music Award for Top Music Video ("Madonna Live: The Virgin Tour").
    
1987

- Jan (10) "Papa Don't Preach" is honored as America's Most Popular Video and World's Favorite Video at the 1st annual World Music Video Awards, produced by Canada's MuchMusic and Europe's Sky Channel.
- (26) Madonna makes a surprise appearance at the 14th annual American Music Awards at the Shrine Auditorium, Los Angeles, CA, to accept her award for Favorite Pop/Rock Female Video Artist ("Papa Don't Preach").
- Feb (3) True Blue is certified 4x platinum (4 million units).
- (7) "Open Your Heart" hits US #1.
- (26) Madonna wins Best Female Singer and Sexiest Female Artist in Rolling Stone magazine's 11th annual Readers Poll.
- Mar "La Isla Bonita" single and video are released. Madonna is voted "Favorite Artist Of Record Pirates" by Billboard magazine.
- (4) Shanghai Surprise is released on home video.
- (15) Madonna is named Favorite Female Musical Performer at the 13th annual People's Choice Awards.
- (29) Madonna wins a Razzie Award for Worst Actress in Shanghai Surprise at the 7th annual Golden Raspberry Awards at the Hollywood Roosevelt Hotel Blossom Ballroom, Los Angeles, CA.
- (30) Madonna is a presenter at the 59th annual Academy Awards at the Dorothy Chandler Pavilion, Los Angeles, CA.
- Apr Madonna begins rehearsals for "Who's That Girl World Tour 1987".
- (2) Madonna wins Best Female Performance for "Papa Don't Preach" at the 5th annual American Video Awards at the Scottish Rite Auditorium, Los Angeles, CA.
- (25) Madonna becomes the only female solo artist to have 4 No. 1 singles in UK with "La Isla Bonita".
- May (2) "La Isla Bonita" hits US #4.
- (18) Madonna is honored for Best Songwriting for "Live To Tell" at the 4th annual ASCAP Pop Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA; the award is accepted on her behalf by brother-in-law Christopher Penn.
- Jun (9) Madonna makes her first TV talk-show appearance on NBC-TV's The Tonight Show (hosted by Johnny Carson).
- (14,15) "Who's That Girl World Tour 1987" opens at the Nishinomiya Stadium, Osaka, Japan.
- (20,21,22) Madonna performs 3 sold-out concerts at Korakuen Stadium, Tokyo, Japan. (During the Japanese leg of the tour, Madonna is honored with The Grand Prix Artist Of The Year Award by the Recording Industry Assocation of Japan).
- (27) Madonna opens the 19-city North American leg of "Who's That Girl World Tour 1987" at the Orange Bowl, Miami, FL.
- (29) Madonna performs at The Omni, Atlanta, GA.
- Jul "Who's That Girl" single and video (from Who's That Girl) are released.
- (2) Madonna performs at Robert F. Kennedy Memorial Stadium, Washington, DC.
- (4) Madonna performs at CNE Stadium, Toronto, ON, Canada.
- (6,7) Madonna performs 2 sold-out concerts at The Forum, Montreal, QC, Canada.
- (9) Madonna performs at Sullivan Stadium, Foxboro, MA.
- (11) Madonna performs at the Veterans Stadium, Philadelphia, PA.
- (13) Madonna performs an AIDS benefit concert in memory of her friend Martin Bourgoyne at Madison Square Garden, New York, NY, which raises $400,000 for the American Foundation For AIDS Research (AMFAR).
- (14) Like A Virgin is certified 7x platinum (7 million units).
- (15) Madonna performs at the Kingdome, Seattle, WA.
- (18) Madonna performs at Anaheim Stadium, Anaheim, CA.
- (20,21) Madonna performs 2 sold-out concerts at the Shoreline Amphitheatre, Mountain View, CA.
- (21) Who's That Girl: Original Motion Picture Soundtrack LP is released.
- (24) Madonna performs at the Astrodome, Houston, TX.
- (26) Madonna performs at Texas Stadium, Irving, TX.
- (29) Madonna performs at St. Paul Civic Centre, St. Paul, MN.
- (31) Madonna performs at Soldier Field, Chicago, IL.
- Aug (2) Madonna performs at the Alpine Valley Music Theatre, East Troy, WI.
- (4,5) Madonna performs at Richfield Coliseum, Richfield, OH.
- (5) Madonna is interviewed by Jane Pauley on NBC-TV's Today and causes a controversy when she refers to her hometown of Bay City, MI as "a smelly little town" - a comment which enrages the citizens of Bay City.
- (6) Madonna attends the New York premiere of Who's That Girl at The National Theatre in Times Square.
- (7) Who's That Girl is released nationwide. Madonna performs at the Pontiac Silverdome, Pontiac, MI and apologizes to 42,000 fans for the comments she made about her hometown on NBC-TV's Today.
- (9) Madonna performs at Giants Stadium, East Rutherford, NJ. Who's That Girl grosses $2.5 million US on its opening weekend.
- (11) True Blue is certified 5x platinum (5 million units).
- (15) Madonna opens the European leg of "Who's That Girl World Tour 1987" at Roundhay Park, Leeds, England.
- (16) Madonna celebrates her 29th birthday at the Groucho Club, London, England.
- (18,19,20) Madonna performs 3 sold-out concerts at Wembley Stadium, London, England.
- (22) Madonna performs to a sold-out crowd of 250,000 at Wald Stadium, Frankfurt, Germany. "Who's That Girl" hits US #1.
- (25,26) Madonna performs at Feyenoord Stadium, Rotterdam, Holland.
- (28) Madonna arrives in Paris, France and attends a reception at City Hall to meet French prime minister Jacques Chirac and his family; she presents him with a cheque for $85,000 to benefit AIDS charities in France.
- (29) Madonna performs for 130,000 people at Parc de Sceaux, Paris, France - the highest attendance at a concert in France.
- (31) Madonna performs at Stade de l'Ouest, Nice, France.
- Sep "Causing A Commotion" single (from Who's That Girl) is released.
- (4) Madonna performs "Causing A Commotion" live by via satellite from the Stadio Communale, Turin, Italy and wins Best Female Video for "Papa Don't Preach" at the 4th annual MTV Video Music Awards at the Universal Amphitheatre, Los Angeles, CA.
- (6) "Who's That Girl World Tour 1987" ends at the Stadio Communale, Florence, Italy.
- (12) Who's That Girl: Original Motion Picture Soundtrack hits US #7.
- (29) Who's That Girl: Original Motion Picture Soundtrack is certified 1x platinum (1 million units).
- Oct (5) Madonna is named top-earning female entertainer of 1987 by Forbes magazine.
- (12) Madonna contributes "Santa Baby" (a remake of 1953 Eartha Kitt song) to Special Olympics LP A Very Special Christmas.
- (24) "Causing A Commotion" hits US #2.
- Nov (2) True Blue wins International Album Of The Year at the 17th annual Juno Awards at the O'Keefe Centre, Toronto, ON.
- (11) Who's That Girl is released on home video.
- (17) You Can Dance, a greatest dance hits remix LP, is released.
- Dec Madonna is honored in The Guinness Book Of Records 1988 as the most successful singer for selling over 11 million copies of True Blue which hit #1 in 28 countries and establishing herself as the world's highest selling solo singing artiste.
- (4) Madonna files for divorce from Sean in Los Angeles County Superior Court, Los Angeles, CA.
- (16) Madonna and Sean decide to reconcile and she withdraws divorce papers filed in Los Angeles, CA on Dec 4.
- (17) "The Look Of Love" (from Who's That Girl) is released as a UK single and hits #9.
- (24) Madonna begins filming Bloodhounds Of Broadway, starring Matt Dillon and Jennifer Grey, directed by Howard Brookner.
- (26) Madonna wins 3 Billboard Music Awards: Top Pop Singles Artist, Top Pop Singles Artist - Female and Top Dance Sales Artist.
     
1988

- Jan In Italy, Madonna is the centre of a controversy between Roman Catholic groups and the residents of Pacentro who want to honor Madonna with the unveiling of a 13-foot statue of her dressed in a bustier; the Vatican and the mayor of Pacentro are outraged and fear that a statue of Madonna as a role model might corrupt the morals of Italian youths.
- (20) You Can Dance is certified 1x platinum (1 million units).
- (23) You Can Dance hits US #14.
- Feb (23) Madonna begins rehearsals in New York, NY for David Mamet's play Speed-The-Plow, co-starring with Joe Mantegna and Ron Silver, directed by Gregory Mosher.
- Mar (10) Madonna wins Worst Female Singer, Worst-Dressed Female Artist and Sexiest Female Artist in Rolling Stone magazine's 12th annual Readers Poll.
- (23) Madonna is certified 4x platinum (4 million units).
- (29) "Madonna Live: The Virgin Tour" video is certified multi-platinum (100,000 units).
- Apr (10) Madonna wins a Razzie Award for Worst Actress in Who's That Girl at the 8th annual Golden Raspberry Awards at the Hollywood Roosevelt Hotel Blossom Ballroom, Los Angeles, CA.
- May (3) Speed-The-Plow opens on Broadway at the Royale Theatre, New York, NY.
- (24) "Madonna - Ciao Italia: Live From Italy" is released on home video.
- Jun (5) Madonna presents a special award to the founders of the South Coast Repertory of Costa Mesa, CA at the 42nd annual Tony Awards at the Minskoff Theatre, New York, NY.
- (27) Madonna and Sean attend the Mike Tyson vs Leon Spinks heavyweight fight at Trump Plaza Hotel & Casino, Atlantic City, NJ.
- Jul (1) Madonna makes a surprise unscheduled appearance on NBC-TV's Late Night With David Letterman.
- (23) "Madonna - Ciao Italia: Live From Italy" hits US #1 on Top Music Videos chart.
- Aug (16) Madonna and Sean celebrate her 30th birthday and their 3rd wedding anniversary at a private party in New York, NY.
- Sep (4) Madonna plays her final performance in Speed-The-Plow on Broadway.
- (11) Madonna participates in "Sport Aid 88: The Race Against Time" marathon in New York, NY.
- (26) Madonna begins recording Like A Prayer LP in Los Angeles, CA with producers Patrick Leonard and Stephen Bray.
- Oct (5) "Madonna - Ciao Italia: Live From Italy" video is certified 1x platinum (100,000 units).
- Nov (16) Madonna attends the opening night of HurlyBurly (starring Sean Penn) at the Westwood Playhouse, Los Angeles, CA.
- Dec (12) Madonna signs a 2-year film contract with Columbia Pictures.
- (28) Madonna files assault charges against Sean at the sheriff's office in Malibu, CA: various newspapers and tabloids will report that Sean burst into their house and tied Madonna to a chair for 9 hours - both Madonna and Sean deny the stories.
- (31) Madonna and Sean are officially separated and will begin divorce proceedings.
    
1989

- Jan (5) Madonna files for divorce citing "irreconcilable differences" in Los Angeles County Superior Court, Los Angeles, CA.
- (18) Madonna purchases a $3 million estate in the Hollywood Hills, Hollywood, CA.
- (25) Madonna signs a $5 million contract with Pepsi-Cola for a series of TV commercials and sponsorship of a world tour.
- Feb (2) Madonna begins filming Dick Tracy, starring and directed by Warren Beatty. (During the year 1989-90, Madonna and Beatty will be involved in a highly-publicized romantic affair).
- (26) Madonna participates in an AIDS Dance-A-Thon benefit at the Shrine Auditorium, Los Angeles, CA.
- Mar (2) The Pepsi commercial "Make A Wish" premieres on NBC-TV's The Cosby Show and is seen by 250 million viewers in 40 countries - she is the first artist to use a new song ("Like A Prayer") in a promotional campaign before its official release.
- (3) "Like A Prayer" video premieres on MTV.
- (4) In Italy, the Roman Catholic group Famiglia Domani protest against the TV broadcast of "Like A Prayer" video and threatens legal court action for blasphemy because of its controversial religious symbolisms.
- (7) "Like A Prayer" single is released.
- (21) Like A Prayer LP is released.
- (30) The Reverend Donald Wildmon of the American Family Association (AFA) threatens a 1-year boycott of all Pepsi-Cola products due to "Like A Prayer" video controversy only if the company doesn't cancel its sponsorship of Madonna.
- Apr (4) Pepsi-Cola announces it has banned all US broadcasts of Madonna's commercial, cancelled her 1-year contract and sponsorship of a world tour due to numerous complaints and boycott threats from religious groups against her video.
- (5) Pepsi-Cola Canada announces it will continue to broadcast Madonna's commercial in spite of "Like A Prayer" video controversy.
- (22) Like A Prayer hits US #1 for 6 weeks and "Like A Prayer" hits US #1 for 3 weeks.
- May (9) "Express Yourself" single is released.
- (10) "Express Yourself" video (filmed on a $5 million budget - the highest in music video history) premieres on MTV.
- (16) "Like A Prayer" single is certified 1x platinum (1 million units).
- (23) Like A Prayer is certified 2x platinum (2 million units).
- (24) Madonna participates in "Don't Bungle The Jungle" benefit concert to save the world's rain forests at the Brooklyn Academy of Music, Brooklyn, NY: she performs a rendition of Sonny & Cher's "I Got You Babe" with comic Sandra Bernhard.
- (31) Madonna wins Best Female Vocalist at the 1st annual International Rock Awards at Lexington Avenue Armory, Manhattan, NY.
- Jul (15) "Express Yourself" hits US #2.
- Aug (11) "Express Yourself" single is certified gold (500,000 units).
- (16) Madonna celebrates her 31st birthday with Warren Beatty and other friends at the club Rubber, Los Angeles, CA.
- (21) "Cherish" video premieres on MTV.
- (29) "Cherish" single is released.
- Sep (1) Madonna is named Top Female Artist Of The 80s and the Artist With The Most Consecutive Top 10 Hits In The 80s with a total of 16 on the American Top 40 Book of Records countdown of the 1980s.
- (6) Madonna performs "Express Yourself" and presents the Video Vanguard Award to George Michael at the 6th annual MTV Video Music Awards at the Universal Amphitheatre, Los Angeles, CA; "Express Yourself" wins Best Direction, Best Art Direction, Best Cinematography and "Like A Prayer" wins the Viewer's Choice Award.
- (19) Madonna and Sean's divorce is finalized.
- (21) Madonna is featured in People magazine's list of the "20 Who Defined The Decade".
- Oct (7) "Cherish" hits US #2 - Madonna overtakes The Beatles on the list of all-time consecutive top 5 singles in US (16 singles) and is also tied with Michael Jackson for the artist with the most consecutive top 10 singles in the 1980s (17 singles).
- (14) Madonna is named one of The Greatest Artists Of The Decade on NBC-TV's Friday Night Videos.
- (24) Madonna is chairperson for the AIDS benefit premiere of film It Had To Be You (starring Joe Bologna & Renee Taylor) at the Samuel Goldwyn Theatre, Beverly Hills, CA.
- Nov "Oh Father" single and video are released in US. "Dear Jessie" is released as a UK single and video.
- (2) Madonna is honored as Artist Of The Decade by Musician magazine.
- (3) Bloodhounds Of Broadway is released in New York, NY.
- (16) Madonna is #50 in Rolling Stone magazine's list of "The 100 Greatest Albums Of The 1980s".
- Dec Madonna is voted Artist Of The Decade by her fans on MTV's Rate The 80s special.
- (23) "Dear Jessie" hits UK #5. Madonna wins a Billboard Music Award for Top Adult Contemporary Artist.
- (24) Madonna is #4 on the list of "Top 20 Pop Artists Of The 80s" voted by readers of The Los Angeles Times newspaper.
- (25) Madonna is named one of the "25 Most Intriguing People In The World For 1989" by People magazine.
    
1990
- Jan Warner Bros Records releases a full-page advertisement in magazines which proclaims Madonna as "Artist Of The Decade".
- (6) "Oh Father" hits US #20 and completes her run of 16 consecutive Top 5 singles in US.
- (9,10,11) Madonna holds open auditions for male dancers for her new world tour at Landmark Studios, Hollywood, CA.
- (23) Like A Prayer is certified 3x platinum (3 million units).
- Feb (2) "Keep It Together" single is released.
- (14) Bloodhounds Of Broadway is released on home video.
- Mar Madonna breaks box-office records as 1,500 concert tickets are sold to fans across America in only 68 seconds.
- (1) "Vogue" video premieres on MTV.
- (8) Madonna wins Worst Female Singer and Worst Video ("Like A Prayer") in Rolling Stone magazine's 14th annual Readers Poll.
- (12) Like A Prayer is named The Grand Prix Album Of The Year at the 4th annual Japan Gold Disc Awards in Tokyo.
- (30) "Vogue" single is released.
- (31) "Keep It Together" hits US #8.
- Apr (11) "Keep It Together" single is certified gold (500,000 units).
- (13,14,15) "Blond Ambition World Tour 1990" opens with 3 sold-out concerts at the Marine Stadium, Makuhari, Japan.
- (20,21,22) Madonna performs 3 sold-out concerts at Nishinomiya Stadium, Osaka, Japan.
- (25,26,27) Madonna performs 3 sold-out concerts at Yokohama Stadium, Yokohama, Japan.
- May (1) Madonna guests on Fox-TV's The Arsenio Hall Show.
- (4,5) Madonna opens the 12-city North American leg of "Blond Ambition World Tour 1990" at The Summit, Houston, TX.
- (7,8) Madonna performs at the Reunion Arena, Dallas, TX.
- (11,12,13,15) Madonna performs 4 sold-out concerts at the Sports Arena, Los Angeles, CA.
- (18,19,20) Madonna performs at the Oakland Coliseum, Oakland, CA.
- (19) "Vogue" hits US #1 for 3 weeks.
- (22) I'm Breathless: Music From And Inspired By The Film Dick Tracy CD is released.
- (23) Bloodhounds Of Broadway (originally filmed in 1987-88) premieres on PBS-TV as an "American Playhouse" presentation.
- (23,24) Madonna performs at the Rosemont Horizon, Chicago, IL.
- (25) Madonna cancels a third scheduled concert at the Rosemont Horizon, Chicago, IL, due to laryngitis.
- (26) Madonna is honored with Pop Artist Of The Decade, Dance Artist Of The Decade and Dance Single Of The Decade ("Into The Groove") in Billboard magazine's "Music Of The 80s" Poll.
- (27,28,29) Madonna performs 3 sold-out concerts at the SkyDome, Toronto, ON, Canada: on May 29, police officers threaten to arrest her on the grounds of lewd and obscene behavior for a masturbation sequence but no charges are filed.
- (31) Madonna performs at The Palace Of Auburn Hills, Auburn Hills, MI.
- Jun (1) Madonna performs at The Palace Of Auburn Hills, Auburn Hills, MI and invites her father onstage to sing him "Happy Birthday". Madonna is controversially featured grabbing her crotch and breast on the cover of Interview magazine.
- (4,5) Madonna performs at The Centrum, Worcester, MA.
- (6) Madonna cancels a third scheduled concert at The Centrum, Worcester, MA, again due to recurring throat problems.
- (8,9) Madonna performs at the Capital Centre, Landover, MD.
- (10) Madonna and Warren Beatty attend the premiere of Dick Tracy in Washington, DC.
- (11,12,13) Madonna performs at Nassau Coliseum, Uniondale, NY.
- (14) "Vogue" single is certified 1x platinum (1 million units).
- (15) Dick Tracy is released nationwide. Madonna cancels a concert at The Spectrum, Philadelphia, PA, again due to laryngitis.
- (16,17) Madonna performs at The Spectrum, Philadelphia, PA.
- (17) Dick Tracy grosses $23 million at the US box-office on its opening weekend.
- (20,21) Madonna performs 2 sold-out concerts at the Meadowlands Arena, East Rutherford, NJ.
- (22) "Hanky Panky" single is released.
- (23) I'm Breathless: Music From And Inspired By The Film Dick Tracy hits US #2.
- (24) Madonna performs an AIDS benefit concert in memory of artist Keith Haring at the Meadowlands Arena, East Rutherford, NJ, which raises $300,000 for the American Foundation For AIDS Research (AMFAR).
- (28) "Vogue" single is certified 2x platinum (2 million units) - the biggest-selling single by a female artist ever.
- (30) Madonna opens the European leg of "Blond Ambition World Tour 1990" at Eriksberg Stadium, Gothenburg, Sweden.
- Jul (2) In Italy, Roman Catholic groups condemn Madonna's concert as blasphemous due to her controversial show's sex and religion themes and plan to cancel her concerts in Rome and Turin.
- (3,4,6) Madonna performs 3 sold-out concerts at Palais Omnisports de Paris-Bercy, Paris, France.
- (9) Madonna arrives on tour in Rome, Italy and holds a press conference at Rome Airport in which she defends her concert and also voices her opinions on artistic expression and freedom of speech.
- (10) Madonna performs at Stadio Flaminio, Rome, Italy.
- (11) Madonna's second scheduled concert at Stadio Flaminio, Rome, Italy is cancelled due to poor ticket sales and a union strike.
- (13) Madonna performs at Stadio Delle Alpi, Turin, Italy.
- (15) Madonna performs at the Olympic Stadium, Munich, Germany.
- (17) Madonna performs at Westfalenhalle, Dortmund, Germany.
- (20,21,22) Madonna performs 3 sold-out concerts at Wembley Stadium, London, England.
- (24) Madonna performs at Feyenoord Stadium, Rotterdam, Holland.
- (27) Madonna performs a sold-out concert at Vicente Calderon Stadium, Madrid, Spain.
- (28) "Hanky Panky" hits US #10.
- (29) Madonna performs at Balaidos Stadium, Vigo, Spain.
- (30) I'm Breathless: Music From And Inspired By The Film Dick Tracy is certified 2x platinum (2 million units).
- Aug (1) Madonna performs at Olympic Stadium, Barcelona, Spain.
- (5) Madonna - Live! Blond Ambition World Tour 90 is broadcast live on HBO-TV from Stade de l'Ouest, Nice, France and seen in more than 4.3 million households - it is the most-watched entertainment special in the network's 18-year history.
- Sep (6) Madonna performs "Vogue" at the 7th annual MTV Video Music Awards at the Universal Amphitheatre, Los Angeles, CA; "Vogue" wins Best Direction, Best Editing and Best Cinematography.
- (7) Madonna is honored with the Commitment To Life Award and performs "Vogue" at the Commitment To Life IV benefit for AIDS Project Los Angeles (APLA) at the Wiltern Theatre, Los Angeles, CA.
- (18) Madonna attends the New York premiere of Martin Scorsese film GoodFellas at the Museum Of Modern Art.
- (19) "Hanky Panky" single is certified gold (500,000 units).
- Oct (1) Madonna is named the top-earning female entertainer of 1990 by Forbes magazine with an annual income of $39 million. "Madonna: Blond Ambition World Tour Live" is released only on laserdisc.
- (2) Madonna attends the opening night of Martha Graham's 180th ballet "Maple Leaf Rag" at the City Centre, New York, NY.
- (16) Madonna visits Paris, France to attend fashion shows by Jean-Paul Gaultier and Thierry Mugler.
- (22) Madonna is featured in a public service announcement on MTV's Rock The Vote in which she is wrapped in the US flag and urges young people to register and vote; the ad causes a controversy with US Veterans of Foreign Wars who are enraged by her provocative use of the American flag and say that it borders on desecration.
- Nov (8) "Justify My Love" single is released.
- (9) Madonna begins filming "Justify My Love" video at Royal Monceau Hotel in Paris, France, directed by Jean-Baptiste Mondino.
- (13) The Immaculate Collection greatest hits CD and video are released.
- (11) Madonna wins Best Female Solo Singer and Most Fanciable Female at the 3rd annual Smash Hits Awards in London, England.
- (15) Madonna is crowned "The Image Of The Eighties" by Rolling Stone magazine.
- (21) A $1 million lawsuit is filed against Madonna by her neighbor, Donald Robinson, who complains that the trees on her property are obstructing his view of the Hollywood Hills, CA.
- (24) The Immaculate Collection hits UK #1 for nine weeks and is the biggest-selling album in UK by a female solo artist.
- (27) MTV network excecutives announce it has banned "Justify My Love" video due to extremely strong displays of sexuality.
- (28) In Canada, "Justify My Love" video is also banned by MuchMusic network because of its sexual content.
- Dec (1) Madonna is named one of the 10 "Women Of The Year" by Glamour magazine.
- (3) Madonna is interviewed by via satellite from Los Angeles, CA by Forrest Sawyer to discuss censorship and her "Justify My Love" video world premieres in its entirety on ABC-TV's Nightline.
- (6) A Los Angeles Superior Court judge dismisses the $1 million lawsuit against Madonna filed by Donald Robinson and orders her to trim the trees on her property.
- (7) "Justify My Love" is released as the first-ever video single, priced at $9.98.
- (11) Madonna: The Royal Box, a box-set which includes The Immaculate Collection CD/video, postcards and poster, is released.
- (19) Dick Tracy is released on home video.
- (24) Madonna In Concert (taped at Olympic Stadium, Barcelona, Spain on Aug 1, 1990) is broadcast on BBC2-TV.
     
1991
- Jan Madonna begins filming Shadows And Fog, starring John Malkovich and Mia Farrow, directed by Woody Allen.
- (3) Rabbi Abraham Cooper of the Simon Wiesenthal Center, Los Angeles, CA, accuses Madonna of anti-semetism over the lyrics of "Justify My Love" CD single remix called "The Beast Within" and wants copies of her single removed from record stores
- (4) Madonna releases a statement of denial about the anti-semetic lyrics of "Justify My Love" CD single remix: "I certainly didn't have any anti-semetic intent when I included a passage from the Bible on my record. It was a commentary on evil in general. My message, if any, is pro-tolerance and antihate. The song is, after all, about love".
- (5) "Justify My Love" hits US #1.
- (13) Madonna presents the Best Foreign Film award for The Nasty Girl to its director Michael Verhoeven at the 56th annual New York Film Critics Circle Awards in the Rainbow Room at Rockefeller Plaza, New York, NY.
- (18) The Immaculate Collection is certified 2x platinum (2 million units).
- (19) "The Immaculate Collection" hits US #1 and "Justify My Love" hits US #2 on Top Music Videos chart.
- (26) The Immaculate Collection hits US #2.
- (28) "Vogue" wins Favorite Dance Single at the 18th annual American Music Awards at the Shrine Auditorium, Los Angeles, CA.
- Feb (2) "Madonna: Blond Ambition World Tour Live" hits US #2 on Top Laserdisc Sales chart.
- (6) "The Immaculate Collection" video is certified multi-platinum (150,000 units).
- (18) "Crazy For You" is re-released as a UK single.
- (21) "Rescue Me" single is released.
- (22) "Justify My Love" single is certified 1x platinum (1 million units), "Justify My Love" video is certified 8x platinum (400,000 units).
- (25) Madonna presents a lifetime achievement award to Andrew Lloyd Webber at the Los Angeles Music Centre Benefactors' dinner at the Regent Beverly Wilshire Hotel, Beverly Hills, CA.
- (27) "The Immaculate Collection" video is certified 2x platinum (200,000 units).
- Mar (2) "Crazy For You" hits UK #2. "Rescue Me" enters the US singles chart at #15 - the highest entry by a female artist.
- (3) "Vogue" wins International Single Of The Year at the 20th annual Juno Awards at the Queen Elizabeth Theatre, Vancouver, BC.
- (7) Madonna wins Best Single ("Vogue"), Best Video ("Vogue"), Best Tour (Blond Ambition Tour), Best-Dressed Female Artist and Sexiest Female Artist in Rolling Stone magazine's 15th annual Readers Poll.
- (20) "Madonna" video is certified multi-platinum (100,000 units).
- (23) "Rescue Me" hits US #9.
- (25) Madonna performs "Sooner Or Later" from Dick Tracy at the 63rd annual Academy Awards at the Shrine Auditorium, Los Angeles, CA and it wins the Oscar for Best Original Song by Stephen Sondheim; her escort at the awards is Michael Jackson.
- Apr (21) Madonna participates in the 3rd annual AIDS Dance-A-Thon at the Sports Arena, Los Angeles, CA.
- May (6) Madonna attends the Los Angeles premiere of Truth Or Dare, a film documentary of "Blond Ambition World Tour 1990", directed by Alek Keshishian, at the Pacific Cinerama Dome.
- (7) Madonna admits to her bisexuality in a controversial 2-part interview with The Advocate magazine.
- (8) Madonna attends the New York premiere of Truth Or Dare at the Ziegfeld Theatre.
- (9) "Like A Virgin" video (from Truth Or Dare) premieres on MTV. Madonna is interviewed on ABC-TV's Good Morning America.
- (10) Truth Or Dare is released nationwide.
- (11) Madonna makes a special guest appearance in "Wayne's World" skit on NBC-TV's Saturday Night Live.
- (12) Madonna arrives in Cannes, France for the 44th International Cannes Film Festival.
- (13) Madonna attends the premiere of Truth Or Dare at the Cannes Film Festival. (In Europe, it is re-titled In Bed With Madonna).
- (13,14) Madonna is featured in a 2-part interview with Regis Philbin on CBS-TV's Live With Regis & Kathie Lee.
- (15) In Bed With Madonna is released in France.
- (16) Madonna attends the premiere of Spike Lee's Jungle Fever at the Cannes Film Festival.
- (17) Truth Or Dare is released to 538 US movie theatres.
- (19) Truth Or Dare hits #3 at the US box-office with $3.38 million on its opening weekend.
- (22) Madonna attends model Naomi Campbell's 21st birthday party at Laura Belle restaurant, New York, NY.
- (24) "Rescue Me" single is certified gold (500,000 units).
- Jun (6) "Holiday" video (from Truth Or Dare) premieres on MTV.
- (15) "Holiday" is re-released as a UK single and hits #5.
- Jul (8) Madonna begins filming A League Of Their Own, starring Tom Hanks and Geena Davis, directed by Penny Marshall.
- (17) In Bed With Madonna premieres at the Marble Arch Odeon in London, England.
- (18) Madonna is named one of the "50 Most Beautiful People Of 1991" by People magazine.
- Aug (7) Madonna attends the Los Angeles premiere of film Paris Is Burning.
- Sep (5) "The Immaculate Collection" wins Best Long-Form Video at the 8th annual MTV Video Music Awards at the Universal Amphitheatre, Los Angeles, CA.
- Oct (9) Truth Or Dare is released on home video.
- (27) Madonna wins Best Female Solo Singer and Most Fanciable Female at the 4th annual Smash Hits Awards in London, England.
- (30) Madonna completes filming A League Of Their Own in Evansville, IN.
- Nov (23) Madonna is named Most Popular International Solo Female Artist at the 1st annual Australian Music Awards.
- (27) Madonna contributes a pre-taped monologue on ABC-TV special MTV 10.
- Dec (4) The Immaculate Collection is certified 3x platinum (3 million units). A rumor is announced that Madonna has tested HIV positive for AIDS: a statement denying the rumor is released by her representatives.
- (8) In a TV Guide magazine interview, Madonna causes a controversy when she complains about filming A League Of Their Own in Evansville, IN: she calls the town "boring", complains that the house she rented didn't have cable and says, "I may as well have been in Prague" - the citizens of Evansville are enraged by her comments: 300 townspeople gather in a parking lot to spell her name inside a circle with a line through it and send her a televised message: "Madonna, get a life!".
- (10) Madonna is honored with the Award Of Courage by the American Foundation For AIDS Research (AMFAR) at a Regent Beverly Wilshire Hotel dinner, Beverly Hills, CA.
     
1992

- Jan Madonna and photographer Steven Meisel begin work on a book of erotica and sexual fantasies in Miami, FL.
- (21) A lawsuit is filed against Madonna by 3 ex-dancers: Oliver Crumes, Kevin Stea and Gabriel Trupin - they are charging her with invasion of privacy, fraud and deceit, intentional misrepresentation, suppression of fact, and intentional infliction of emotional distress for exposing their private lives in her 1991 film documentary Truth Or Dare.
- Feb (22) Madonna makes a surprise guest appearance in "Coffee Talk" skit with Mike Myers, Roseanne Arnold and Barbra Streisand on NBC-TV's Saturday Night Live.
- (25) "Madonna: Blond Ambition World Tour Live" wins Best Music Video - Long Form at the 34th annual Grammy Awards at Radio City Music Hall, New York.
- Mar (5) Madonna wins Best-Dressed Female Artist in Rolling Stone magazine's 16th annual Readers Poll.
- (20) Shadows And Fog is released.
- (30) Madonna attends Swifty Lazar's annual post-Academy Awards party at Spago's restaurant, Los Angeles, CA.
- Apr Madonna begins filming Body Of Evidence, co-starring Willem Dafoe and directed by Uli Edel.
- (20) Madonna signs a $60 million, seven-year contract with Time Warner Inc. as a joint venture to form a new multi-media entertainment company: she is made CEO of her own record and music publishing company called Maverick, which will also include TV, film, merchandising and book publishing divisions; she also re-negotiates and extends her contract with Sire Records: a $5 million advance per album, a 20% royalty rate and all her future recordings will be released by Maverick/Sire Records.
- (30) A black bustier worn by Madonna in "Open Your Heart" video is stolen from Frederick's Of Hollywood's lingerie museum during the 3-day riots in Los Angeles, CA.
- May (6) Frederick's Of Hollywood, Los Angeles, CA offers a $1,000 reward for the return of Madonna's bustier.
- (29) The FBI recovers 44 nude photographs of Madonna from a collection used for her upcoming Sex book: a man is arrested in West Hollywood, CA for trying to sell the pictures for $100,000 to an undercover FBI agent.
- Jun (8) Madonna begins recording sessions for Erotica album at Soundworks, New York, NY.
- (16) Madonna and Rosie O'Donnell (co-star of A League Of Their Own) guest together on Fox-TV's The Arsenio Hall Show.
- (18) "This Used To Be My Playground" single (from A League Of Their Own) is released.
- (25) Madonna attends the New York premiere of A League Of Their Own at the Ziegfeld Theatre.
- (30) "This Used To Be My Playground" video premieres on MTV. Madonna contributes a remixed version of "Supernatural" (originally released on B-side of "Cherish" single in 1989) to AIDS benefit CD Red Hot & Dance.
- Jul (1) A League Of Their Own is released nationwide.
- (7) Madonna contributes "This Used To Be My Playground" to Special Olympics benefit CD Barcelona Gold.
- Aug (8) "This Used To Be My Playground" hits US #1.
- (16) "Madonnathon 92: The 1st International Madonna Appreciation Convention" is held at the Holiday Inn, Southfield, MI.
- Sep (10) "This Used To Be My Playground" single is certified gold (500,000 units).
- (23) Madonna is featured in a public service announcement on MTV's Rock The Vote.
- (24) Madonna exposes her breasts in front of 6,000 people at a Jean-Paul Gaultier fashion show benefit at the Shrine Auditorium, Los Angeles, CA; the show raises $750,000 for the American Foundation For AIDS Research (AMFAR).
- Oct (2) "Erotica" video premieres on MTV.
- (4) Madonna visits Milan, Italy to begin her Sex and Erotica promotional tour: she attends the opening of Milanese Fashion Week and is presented with a Telegatto Award for Best International Female Artist.
- (5) Madonna is guest of honor at a disco party hosted by Italian designers Dolce and Gabbana in Milan, Italy. In US, NBC-TV's Friday Night Videos announces it will not broadcast "Erotica" video because of its controversial images of sex and bondage.
- (7,8) Madonna visits Hamburg, Germany to promote Sex and Erotica.
- (9) In Paris, it is announced that Madonna owes $2 million to the French government in back taxes from 2 concerts in 1987.
- (10) Madonna visits Paris, France on her Sex and Erotica promotional tour.
- (11) Madonna guests on 7 Sur 7 TV show in Paris, France.
- (12) Madonna visits London, England to complete Sex and Erotica promotional tour.
- (13) "Erotica" single is released. Madonna is interviewed on BBC1-TV's Jonathan Ross Presents …
- (14) Madonna denies she owes $2 million to France in back taxes and says: "I think the commissioner just wants to meet me".
- (15) Madonna is guest of honor at her Sex book party at the Industria Superstudio, Manhattan, NY.
- (20) Erotica CD is released.
- (21) Sex, a 128-page book of erotica and sexual fantasies written by Madonna, photographed by Steven Meisel, designed by Fabien Baron and edited by Glenn O'Brien, is released; the spiral-bound, metal-covered book is wrapped in a silver mylar bag with a copy of "Erotica" CD single, an 8-page comic book and priced at $49.95 US. Shadows And Fog is released on home video.
- (22) Sex has sold a record 150,000 US copies on its first day of release.
- (23) In Europe, Sex has sold over 100,000 copies in 2 days: England (100,000), France (25,000) and sold-out in Australia.
- (24) "Erotica" hits US #3.
- (26) In Japan, Sex is banned due to its controversial photos which violate the country's censorship law.
- (30) In Mesa, AZ, public libraries have cancelled Sex book orders after local residents have called to protest its purchase.
- (31) Sex has sold a record 500,000 copies in only one week.
- Nov (1) Sex hits #1 on the Washington Post non-fiction bestseller list.
- (3) Sex is banned in New Delhi, India and police officials announce they will confiscate copies of the book entering the country.
- (7) Erotica hits US #2.
- (8) Sex hits #1 on the New York Times non-fiction bestseller list.
- (16) Madonna attends the New York premiere of Spike Lee film Malcolm X at the Ziegfeld Theatre.
- (21) Madonna is named Most Popular International Solo Female Artist at the 2nd annual Australian Music Awards.
- (24) "Deeper And Deeper" video premieres on MTV.
- (26) In Paris, a Catholic group called The Future Of Culture files 2 lawsuits against Madonna and her publisher for corrupting the French youth with pornography and to have all copies of Sex book destroyed.
- Dec (1) Mayor Tom Bradley of Los Angeles, CA declares this day "Frederick's Of Hollywood Day" to celebrate the return of Madonna's bustier which was stolen on April 30 during the Los Angeles riots.
- (6) Madonna wins Best Female Solo Singer and Most Fanciable Female at the 5th annual Smash Hits Awards in London, England.
- (7) The Future Of Culture group loses a court battle against Madonna to have copies of her book destroyed in France.
- (10) "Deeper And Deeper" single is released. "Erotica" single is certified gold (500,000 units).
- (14) Madonna wins the Sour Apple Award given to a celebrity "who most believes his or her own popularity" from the Hollywood Women's Press Club at the 52nd annual Golden Apple Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
- (19) Sex is voted Hype Of The Year by readers of NME magazine in UK.
- (28) Madonna is named one of the "25 Most Intriguing People In The World For 1992" by People magazine.
    
1993
- Jan (6) Erotica is certified 2x platinum (2 million units).
- (9) Madonna attends a press conference to promote her new film Body Of Evidence at the Rihga Royal Hotel, Manhattan, NY.
- (11) Madonna is interviewed by Valerie Pringle on CTV's Canada A.M. and on ABC-TV's Entertainment Tonight.
- (14,15) Madonna is featured in a 2-part interview with Bryant Gumbel on NBC-TV's Today.
- (15) Body Of Evidence is released nationwide.
- (16) Madonna is musical guest on NBC-TV's Saturday Night Live: she performs "Fever" and "Bad Girl".
- 17) Body Of Evidence grosses $6.5 million at the US box-office on its opening weekend.
- (18) Madonna is interviewed on CBS-TV's This Morning.
- (20) Madonna guests on Parita Doppia TV show to promote Body Of Evidence in Rome, Italy.
- (30) "Deeper And Deeper" hits US #7.
- Feb (8) Madonna begins filming Dangerous Game, co-starring Harvey Kietel and James Russo, directed by Abel Ferrerra.
- (11) "Bad Girl" video premieres on MTV.
- (17) A League Of Their Own is released on home video.
- (25) "Bad Girl" single is released.
- Mar (4) Madonna wins Worst Video ("Erotica"), Worst Album Cover (Erotica) and Sexiest Female Artist in Rolling Stone magazine's 17th annual Readers Poll.
- (22) "Fever" (a remake of 1958 Peggy Lee song) is released as a UK single.
- (27) "Bad Girl" hits US #36.
- Apr (3) "Fever" hits UK #6. (In US, "Fever" is unreleased as a single and only appears on B-side of "Bad Girl" CD maxi-single).
- (27) Madonna is honored for Best Songwriting for "This Used To Be My Playground" at the 8th annual ASCAP Film & Television Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
- May (11) "Fever" video premieres on MTV.
- (13) Madonna performs "Fever" and a rendition of "The Lady Is A Tramp" on the 1,000th episode of The Arsenio Hall Show at the Hollywood Bowl, Hollywood, CA. (The show will air on Fox-TV on May 14).
- Jun (16) Madonna signs a contract with ABC-TV to jointly develop and produce TV specials, movies and a 4-hour miniseries.
- (18) Body Of Evidence is released on home video.
- (21) "Rain" video premieres on MTV. Madonna attends the New York premiere of film Sleepless In Seattle.
- Jul (1) "Rain" single is released.
- (8) Madonna begins rehearsals for a new tour called "The Girlie Show".
- Aug Madonna interviews Rosie O'Donnell for an article titled "Coming Up Rosie!" in Mademoiselle magazine.
- Sep (2) Madonna performs "Bye Bye Baby" at the 10th annual MTV Video Music Awards at the Universal Amphitheatre, Los Angeles, CA; "Rain" wins Best Art Direction and Best Cinematography.
- (9) Dangerous Game premieres at the 50th annual Venice Film Festival in Venice, Italy.
- (11) "Rain" hits US #14.
- (20) The Immaculate Collection is certified 4x platinum (4 million units).
- (25,26) "The Girlie Show" opens with 2 sold-out concerts at Wembley Stadium, London, England.
- (28,29, Oct 1) Madonna performs at Palais Omnisports de Paris-Bercy, Paris, France.
- Oct (2) Madonna's concert at the Festhalle in Frankfurt, Germany is cancelled due to technical difficulties.
- (4) Madonna performs at Hayarkon Park, Tel Aviv, Israel, despite protests staged earlier by jewish groups to cancel her show.
- (5) Madonna is profiled on A&E-TV's Biography.
- (7) Madonna performs at Inonu Stadium, Istanbul, Turkey.
- (11,12) Madonna opens the North American leg of "The Girlie Show" at the SkyDome, Toronto, ON, Canada.
- (13) Madonna attends the New York premiere of film Farewell, My Concubine, co-released by Maverick Pictures for US release.
- (14) Rolling Stone: The 100 Top Music Videos includes "Express Yourself" #10, "Like A Prayer" #20, "Borderline" #24, "Vogue" #28, "Justify My Love" #43 and "Oh Father" #66 - Madonna has more videos on the list than any other artist or group.
- (14,15,17) Madonna performs 3 sold-out concerts at Madison Square Garden, New York, NY.
- (19) Madonna performs at The Spectrum, Philadelphia, PA.
- (21) Madonna performs at The Palace Of Auburn Hills, Auburn Hills, MI.
- (23) Madonna performs at Olympic Stadium, Montreal, QC, Canada.
- (26) Madonna performs at Juan Ramon Loubriel Stadium, San Juan, Puerto Rico and causes a controversy when she pulls a Puerto Rican flag to her crotch in front of 26,000 fans; the Puerto Rican House of Representatives charges her with desecration of the flag and passes a resolution to condemn her.
- (30,31) Madonna performs at the River Plate Stadium, Buenos Aires, Argentina.
- Nov (3) Madonna performs at Morumbi Stadium, Sao Paulo, Brazil.
- (6) Madonna performs to a sold-out crowd of 120,000 at Maracana Stadium, Rio de Janeiro, Brazil.
- (10,12,13) Madonna performs 3 sold-out concerts at Hermanos Rodriguez Autodromo, Mexico City, Mexico (which grosses a record $8,928,000) despite attempts by religious groups to keep her out of the country.
- (17) Madonna arrives in Sydney, Australia and, as a gift, she is presented with a didgeridoo, a sacred Aboriginal instrument that only men are allowed to play or touch; the Australians are enraged to see her accept it as a gift.
- (19) Madonna performs at Sydney Cricket Ground, Sydney, Australia. Dangerous Game premieres in New York, NY.
- (20) Madonna - Live Down Under: The Girlie Show (taped Nov 19 at Sydney Cricket Ground) is broadcast on HBO-TV. In Australia, Madonna cancels a scheduled concert at Sydney Cricket Ground due to severe weather conditions.
- (24) Madonna performs at Brisbane Anz Stadium, Brisbane, Australia.
- (26,27,29) Madonna performs 3 sold-out concerts at Melbourne Cricket Ground, Melbourne, Australia.
- (27) Madonna is named Most Popular International Solo Female Artist at the 3rd annual Australian Music Awards.
- Dec (1) Madonna performs at Adelaide Oval, Adelaide, Australia.
- (3,4) Madonna performs 2 sold-out concerts at Sydney Cricket Ground, Sydney, Australia.
- (7,8,9) Madonna performs at the Fukuoka Dome, Fukuoka, Japan.
- (13,14,16,17,19) "The Girlie Show" ends with 5 sold-out concerts at the Tokyo Dome, Tokyo, Japan.
     
1994

- Mar (8) "I'll Remember (Theme From The Motion Picture With Honors)" single is released.
- (12) Madonna makes a surprise unannounced appearance at the AIDS Dance-A-Thon benefit in San Francisco, CA.
- (15) Madonna attends the 8th annual Soul Train Music Awards at the Shrine Auditorium, Los Angeles, CA.
- (17) "I'll Remember (Theme From With Honors)" video premieres on BBC1-TV's Top Of The Pops.
- (20) Madonna wins a Razzie Award for Worst Actress in Body Of Evidence at the 14th annual Golden Raspberry Awards at the Hollywood Roosevelt Hotel Academy Room, Los Angeles, CA.
- (21) "I'll Remember (Theme From With Honors)" video premieres on MTV.
- (31) Madonna guests on CBS-TV's Late Show With David Letterman: during the 20-minute interview, she says the word "fuck" 13 times, makes obscene remarks and wisecracks, refuses to leave the set and is rude to her host; her lewd and vulgar behavior causes a public and media controversy and Letterman also expresses his displeasure by her appearance on his show.
- Apr (26) "Madonna: The Girlie Show - Live Down Under" is released on home video and laserdisc. Madonna attends the Los Angeles premiere of Alek Keshishian film With Honors.
- May (14) "Madonna: The Girlie Show - Live Down Under" hits US #3 on Top Music Videos chart. Madonna attends the opening of Planet Hollywood restaurant in Miami, FL.
- (18) Madonna makes a surprise appearance on NBC-TV's The Tonight Show (hosted by Jay Leno).
- (28) "I'll Remember (Theme From With Honors)" hits US #2.
- Jun (14) "I'll Remember (Theme From With Honors)" single is certified gold (500,000 units).
- (15) Dangerous Game is released on home video.
- (24) Madonna attends "The Beat Goes On: The LifeBeat Benefit Concert" at the Beacon Theatre, New York, NY.
- Jul Madonna films a cameo appearance as a singing telegram girl for Wayne Wang and Paul Auster movie Blue In The Face.
- (19) Madonna contributes "Goodbye To Innocence" to benefit CD Just Say Roe.
- (26) Madonna files a temporary restraining order against 26-year-old Todd Lawrence, a deranged fan who is stalking Madonna at her Los Angeles, CA mansion and also claims to be her husband.
- Aug (23) Todd Lawrence is sentenced to one-year in jail on misdemeanor charges for stalking Madonna.
- Sep (1) Madonna is named Diva Of The Decade by CD Review magazine.
- (8) Madonna and David Letterman present the Best Video Of The Year award to Aerosmith for "Cryin'" at the 11th annual MTV Video Music Awards at Radio City Music Hall, New York, NY.
- (14) "Secret" single is available for downloading on the internet on America Online (AOL) and CompuServe.
- (20) "The Immaculate Collection" video is certified 3x platinum (300,000 units).
- (27) "Secret" single is released.
- (29) Madonna and 3 ex-dancers reach an out-of-court settlement on a lawsuit they filed against her in 1992.
- Oct (4) "Secret" video premieres on MTV.
- (5) Madonna arrives in Paris, France on a promotional tour for her new CD Bedtime Stories.
- (15) Madonna participates in Jean-Paul Gaultier's spring/summer 1995 ready-to-wear collection fashion show in Paris, France.
- (25) Bedtime Stories CD is released.
- Nov (1) Madonna is voted Worst Actress, Worst Female Singer and Most-Overexposed Celebrity in US magazine reader's poll.
- (3) Madonna begins filming "Take A Bow" video in Ronda, Spain, directed by Michael Haussman.
- (5) "Secret" hits US #3.
- (12) Bedtime Stories hits US #3.
- (16) Madonna begins filming Four Rooms: she appears as a witch in "The Missing Ingredient" segment starring Tim Roth, Sammi Davis, Amanda de Cadenet, Valeria Golino, Ione Skye, Lili Taylor, Alicia Witt and directed by Allison Anders.
- (29) Madonna: Innocence Lost, a made-for-TV movie based on Christopher Andersen's 1991 book Madonna Unauthorized, premieres on Fox-TV. (Madonna is played by 26-year-old newcomer Terumi Matthews).
- (30) "Take A Bow" video premieres on MTV.
- Dec (5) Madonna begins filming "Bedtime Story" video at Universal Studios, Los Angeles, CA, directed by Mark Romanek.
- (6) "Take A Bow" single is released.
- (12) Madonna attends the New York premiere of Robert Altman film Ready-To-Wear (Prêt-A-Porter).
    
1995

- Jan Madonna releases her second book: The Girlie Show, with 70-pages of photographs, capital letter text and a 3-song live CD from "The Girlie Show" world concert tour of 1993.
- (5) "Secret" single is certified gold (500,000 units), Bedtime Stories is certified 1x platinum (1 million units).
- (11) Madonna is #10 on Mr. Blackwell's 35th annual list of the worst-dressed women of 1994.
- (30) Madonna and Babyface perform "Take A Bow" at the 22nd annual American Music Awards at the Shrine Auditorium, Los Angeles, CA.
- Feb (9) "Madonna: The Girlie Show - Live Down Under" video is certified gold (50,000 units), Like A Virgin is certified 9x platinum (9 million units) and True Blue is certified 7x platinum (7 million units).
- (13) Madonna makes a surprise appearance on CBS-TV's Late Show With David Letterman.
- (18) Madonna performs "Secret" and "Take A Bow" on Wetten Dass TV show in Ravensburg, Germany.
- (20) Madonna performs "Bedtime Story" at the 14th annual Brit Awards at the Alexandra Palace, London, England.
- (22) Madonna performs "Take A Bow" at the San Remo Song Festival in San Remo, Italy.
- (25) "Take A Bow" hits US #1 for 7 weeks - her first #1 single in 3 years.
- (27) "Take A Bow" single is certified gold (500,000 units), Bedtime Stories is certified 2x platinum (2 million units).
- Mar (1) Madonna begins a series of promotional ad campaigns in various North American magazines for Gianni Versace fashions.
- (13) After 10 years with CAA, Madonna changes agents by signing with the William Morris Agency.
- (15) Madonna is signed to star as the late Eva Peron in film version of Andrew Lloyd Webber's Broadway musical Evita.
- (16) The Immaculate Collection is certified 6x platinum (6 million units).
- (18) Madonna hosts a pajama party for 1,500 fans at Webster Hall, New York, NY, to celebrate the premiere of "Bedtime Story" video broadcast live on MTV and also reads a bedtime story of Miss Spider's Tea Party by David Kirk.
- (21) Madonna is featured in a public service announcement for VH1.
- (27) Madonna attends the post-Academy Awards party at Chasen's restaurant, Los Angeles, CA.
- Apr (13) "Bedtime Story" single is released.
- (25) After signing with the William Morris Agency on March 13, Madonna changes agents again by switching to ICM.
- (29) "Bedtime Story" hits US #42.
- May (6) "Bedtime Story" drops to #52 and completes Madonna's run of 32 consecutive Top 40 US hits.
- (15) "I'll Remember (Theme From With Honors)" is honored as one of the Most Performed Songs Of 1994 at the 12th annual ASCAP Pop Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
- (19) "Human Nature" video premieres on MTV.
- (29) Robert Hoskins, 37, is shot by a security guard outside Madonna's Castillo del Lago estate, Los Angeles, CA for trespassing on her property and threatening to marry or kill Madonna. Hoskins, who is shot in the arm and hip, is arrested on $150,000 US bail; Madonna is not at home during the incident.
- Jun Madonna films a cameo appearance as the madam of a telephone sex service for Spike Lee movie Girl 6.
- (1) Madonna attends the Parkinson's Disease Foundation salute to Muhammad Ali at the Marriott Marquis Hotel, New York, NY.
- (6) "Human Nature" single is released.
- (24) Madonna makes a surprise appearance to introduce a live performance by UNV at KISS-FM and Aquafina's 3rd annual KISS & Unite concert at the Irvine Meadows Amphitheatre, Irvine, CA.
- (27) Madonna reads the poem "If You Forget Me" by Pablo Neruda on The Postman (Il Postino) soundtrack CD.
- Jul (15) "Human Nature" hits US #46.
- Aug (17) Madonna celebrates her 37th birthday party at The Delano Hotel, Miami, FL.
- Sep (7) Madonna presents the Best Rap Video award to Dr. Dre for "Keep Their Heads Ringin'" and wins Best Female Video for "Take A Bow" at the 12th annual MTV Video Music Awards at Radio City Music Hall, New York, NY.
- (24) Madonna arrives in London, England to begin 2-month recording sessions for Evita movie soundtrack.
- Oct (1) Madonna attends the London premiere of film Assassins (starring Antonio Banderas).
- (2) Madonna begins recording Evita soundtrack at CTS Studios, London. "I Want You" video world premieres on VH1.
- (13) Blue In The Face is released in US.
- (17) Madonna (with Massive Attack) contribute a remake of 1976 song "I Want You" to Marvin Gaye tribute CD Inner City Blues: The Music Of Marvin Gaye.
- (18) "You'll See" is available for downloading on the internet at www.wbr.com.
- (19) "I Want You" video is featured on MTV documentary Inner City Blues: The Music Of Marvin Gaye.
- (21) "I Want You" video hits #11 on VH1.
- (23) Madonna begins filming "You'll See" video in London, England, directed by Michael Haussman.
- Nov (2) "You'll See" video premieres on MTV. Madonna performs "You'll See" on BBC1-TV's Top Of The Pops in London, England.
- (7) Something To Remember greatest ballad hits CD is released.
- (21) "You'll See" single is released.
- (22) Madonna is interviewed by Jane Pratt on VH1's VH1 To One.
- (25) Something To Remember hits US #6.
- Dec (3) Madonna attends the 1st annual VH1 Fashion & Music Awards at Lexington Avenue Armory, Manhattan, NY: she presents the Fashion's Future award to Gucci's Tom Ford and receives the Most Fashionable Artist award by ex-husband Sean Penn.
- (13) Madonna is interviewed by Forrest Sawyer on ABC-TV's PrimeTime Live.
- (16) "You'll See" hits US #6.
- (21) Madonna is subpoenaed to testify against her stalker, Robert Hoskins, at the Criminal Courts Building, Los Angeles, CA on Jan 3, 1996; if she ignores the order, a $5 million warrant will be issued for her arrest.
- (23) Madonna wins 2 Billboard Music Awards: Top Hot 100 Singles Artist - Female and Top Hot Dance Club Play Artist.
- (25) Four Rooms is released in US. "Oh Father" is released as a UK single.
  
1996
- Jan (2) The trial of Robert Hoskins begins at the Criminal Courts Building, Los Angeles, CA; Madonna's lawyer, Nicholas DeWitt, files a motion to seek approval from the court that she videotape her testimony, but it is rejected by Judge Jacqueline Connor who orders Madonna to testify in court.
- (3) Madonna appears at the Criminal Courts Building, Los Angeles, CA in Courtroom 116 to testify against Robert Hoskins.
- (6) "Oh Father" hits UK #16.
- (8) Robert Hoskins is found guilty and convicted on 5 charges of assault, stalking and threatening to kill Madonna.
- (11) Madonna is #1 on Mr. Blackwell's 36th annual list of the best-dressed women of 1995.
- (12) Four Rooms is released nationwide.
- (17) Madonna accepts an award for David Bowie, who is unable to attend his induction into the 11th annual Rock N Roll Hall Of Fame at The Waldorf-Astoria Hotel, New York, NY.
- (18) Something To Remember is certified 1x platinum (1 million units).
- (20) Madonna arrives in Buenos Aires, Argentina to begin film production on Evita.
- (25) Madonna receives death threats from Argentine conservatives who are enraged and insulted that she is playing Eva Peron in Evita; since her arrival in Argentina, over 50 walls throughout the city have been spray-painted with the words: Viva Evita! Fuera Madonna! (Long Live Evita! Get Out, Madonna!).
- Feb (6) Madonna and the cast of Evita attend a press conference in Buenos Aires, Argentina.
- (13) Madonna begins filming Evita, co-starring Antonio Banderas, Jonathan Pryce and Jimmy Nail, directed by Alan Parker.
- (24) Madonna is the centre of a controversy when animal-rights group PETA places a full-page advertisement in Billboard magazine as an attack on her for promoting bullfighting in "Take A Bow" and "You'll See" videos.
- (27) "You'll See" single is certified gold (500,000 units).
- Mar (4) Madonna is named Most Successful International Female Artist at the 5th annual Echo Awards in Hamburg, Germany.
- (10) Madonna lip-synchs "Don't Cry For Me Argentina" for a scene in Evita before a crowd of 2,000 extras on the balcony of the Casa Rosada, the same location where the late Eva Peron addressed her people 50 years earlier.
- (11) "One More Chance" is released as a UK single.
- (19) "Love Don't Live Here Anymore" (a remixed version of 1978 Rose Royce song originally recorded by Madonna in 1984 on Like A Virgin album) is released as a US single.
- (22) Robert Hoskins is sentenced to 10-years in jail for stalking and threatening to kill Madonna. Girl 6 is released.
- (23) "One More Chance" hits UK #11.
- (24) Madonna wins a Razzie Award for Worst Supporting Actress in Four Rooms at the 16th annual Golden Raspberry Awards at the Hollywood Roosevelt Hotel Academy Room, Los Angeles, CA. Madonna arrives in Budapest, Hungary to continue filming Evita.
- Apr (1) "Love Don't Live Here Anymore" video premieres on VH1.
- (16) Madonna announces she is 4-months pregnant by her 29-year-old boyfriend and personal trainer, Carlos Leon.
- (29,30) Madonna is interviewed by Bryant Gumbel on NBC-TV's Today.
- May (3) Madonna continues film production on Evita at Shepperton Studios in London, England.
- (18) "Love Don't Live Here Anymore" hits US #78.
- (20) "Take A Bow" is honored as one of the Most Performed Songs Of 1995 at the 13th annual ASCAP Pop Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
- (28) Madonna completes filming Evita in London, England after 84-days of production and a $60 million budget.
- Jun (11) Blue In The Face is released on home video.
- (13) A New Madonna: The Making Of Evita special (hosted by Kurt Loder) premieres on MTV.
- Jul (16) Four Rooms is released on home video.
- (18) Madonna makes a special appearance to introduce a live performance by Me'Shell NdegeOcello at the 9th annual Commitment To Life benefit for AIDS Project Los Angeles (APLA) at the Universal Amphitheatre, Los Angeles, CA.
- Aug (6) Madonna and brother-in-law Joe Henry contribute a remake of "Guilty By Association" to Vic Chesnutt tribute CD Sweet Relief II: Gravity Of The Situation - The Songs Of Vic Chesnutt. Girl 6 is released on home video.
- Oct (8) "You Must Love Me" video premieres on MTV.
- (14) Madonna gives birth to a 6-lb, 9-oz girl, Lourdes Maria Ciccone Leon, at Good Samaritan Hospital, Los Angeles, CA.
- (29) "You Must Love Me" single (from Evita) is released.
- Nov (12) Evita: The Complete Motion Picture Music Soundtrack 2-CD set is released.
- (15) Madonna appears via telephone call from Rosie O'Donnell on CBS-TV's The Rosie O'Donnell Show.
- (18) Something To Remember is certified 2x platinum (2 million units).
- (23) "You Must Love Me" hits US #18.
- Dec (3) "Don't Cry For Me Argentina" video premieres on VH1.
- (4) Madonna is honored with the Artist Achievement Award at the 7th annual Billboard Music Awards at the Aladdin Hotel Theatre For The Performing Arts, Las Vegas, NV. (It is her first public appearance since the birth of her daughter).
- (10) The Making Of Evita book, written by Alan Parker with a preface by Madonna, is released.
- (12) Madonna attends a press conference to promote Evita at the Ritz-Carlton Hotel in Marina Del Rey, CA.
- (13) Madonna guests on CBS-TV's The Oprah Winfrey Show.
- (14) Madonna attends the world premiere of Evita at the Shrine Auditorium, Los Angeles, CA.
- (16) Madonna is profiled on NBC-TV's Access Hollywood and is also featured in an interview on ABC-TV's Entertainment Tonight.
- (17) Madonna is interviewed on CTV's Canada A.M.
- (18) Madonna arrives in London, England to begin her world tour of Evita premieres.
- (19) Madonna attends the premiere of Evita at the Empire Theatre, Leicester Square in London, England.
- (20) Madonna attends the premiere of Evita at the Cinema Etoile in Rome, Italy.
- (23) Madonna completes her world tour of Evita premieres in Madrid, Spain and returns home to US for the Christmas holidays.
- (25) Evita is released in New York, NY and Los Angeles, CA.
- (29) Evita grosses $334,440 during its Christmas holiday release in New York and Los Angeles.
- (30) Madonna is named one of the "25 Most Intriguing People In The World For 1996" by People magazine.
 
1997
- Jan (3) Lourdes Maria Ciccone Leon is baptized at St. Jude Melkite Catholic Church, Miami, FL. Evita is released in 20 US cities.
- (5) Evita hits #20 at the US box-office with $2.22 million during its limited weekend release.
- (9) Madonna guests on CBS-TV's The Rosie O'Donnell Show.
- (9,10) Madonna is featured in a 2-part interview with Matt Lauer on NBC-TV's Today.
- (10) Evita is released nationwide.
- (12) Evita hits #2 at the US box-office with $8.4 million on its nationwide opening weekend (704 theatres).
- (13) Madonna is interviewed on CBS-TV's This Morning.
- (14) Madonna is #3 on Mr. Blackwell's 37th annual list of the best-dressed women of 1996.
- (15) Evita wins Best Motion Picture, Musical Or Comedy at the 1st annual Golden Satellite Awards in Los Angeles, CA.
- (19) Madonna wins Best Actress In A Motion Picture, Musical Or Comedy in Evita at the 54th annual Golden Globe Awards at the Beverly Hilton Hotel, Beverly Hills, CA; Evita wins Best Motion Picture, Musical Or Comedy and "You Must Love Me" wins Best Original Song, Motion Picture (Andrew Lloyd Webber & Tim Rice).
- (24) Evita: The Complete Motion Picture Music Soundtrack is certified 1x platinum (1 million units).
- Feb (1) Evita: The Complete Motion Picture Music Soundtrack hits US #2.
- (11) "Don't Cry For Me Argentina" (from Evita) is released as a maxi-single in US.
- (16) Madonna makes a special appearance at Elizabeth Taylor's 65th birthday party at The Pantages Theatre, Los Angeles, CA.
- (24) Happy Birthday Elizabeth: A Celebration Of Life premieres on ABC-TV.
- Mar (1) "Don't Cry For Me Argentina" hits US #8.
- (3) Madonna is named Most Successful International Female Artist at the 6th annual Echo Awards in Hamburg, Germany.
- (14) Madonna wins the American Moviegoer Award for Outstanding Performance By A Female Actor in Evita.
- (18) "Another Suitcase In Another Hall" (from Evita) is released as a UK single.
- (24) Madonna performs "You Must Love Me" from Evita at the 69th annual Academy Awards at the Shrine Auditorium, Los Angeles, CA and it wins the Oscar for Best Original Song by Andrew Lloyd Webber & Tim Rice.
- (29) "Another Suitcase In Another Hall" hits UK #7.
- Apr (8) Evita: The Complete Motion Picture Music Soundtrack is certified 2x platinum (2 million units).
- (19) Madonna is featured in a special pre-taped video at the 10th annual Nickelodeon's Kids' Choice Awards in Los Angeles, CA.
- (27) Evita has grossed $49 million US and a global total of $140.9 million.
- (29) Madonna contributes "Freedom" (recorded in 1994) to the Rainforest Foundation benefit CD Carnival!.
- May (15) Like A Prayer is named one of the "200 Best Albums Ever Made" by Rolling Stone magazine.
- (19) "You'll See" is honored as one of the Most Performed Songs Of 1996 at the 14th annual ASCAP Pop Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
- (20) "Madonna: The Girlie Show - Live Down Under" (1994) is released on DVD.
- Jun (28) Madonna attends the Mike Tyson vs. Evander Holyfield heavyweight fight at the MGM Grand Garden, Las Vegas, NV.
- (30) Madonna begins recording a new album with producer William Orbit at Larrabee Studios North, Los Angeles, CA.
- Jul (16) Like A Prayer is certified 4x platinum (4 million units).
- (28) Madonna writes a one-page tribute to Time magazine in memory of the late Gianni Versace, who was murdered on July 15.
- (29) Evita: Music From The Motion Picture CD (highlights from Evita soundtrack) is released in US.
- Aug (5) Evita is released on home video.
- (19) "Buenos Aires" (from Evita) is released only to club DJs and radio stations in US to promote Evita on video.
- (26) Truth Or Dare (1991) is released on DVD.
- (30) Evita: Music From The Motion Picture hits US #167.
- Sep (3) In an interview with The London Times, Madonna speaks about the death of Princess Diana, who was killed in a car accident in Paris, France on Aug 31, 1997.
- (4) Madonna makes a special appearance to introduce a live performance by Prodigy at the 14th annual MTV Video Music Awards at Radio City Music Hall, New York, NY.
- (8) Madonna attends a memorial service for Gianni Versace at the Metropolitan Museum of Art, Manhattan, NY.
- (9) A League Of Their Own (1992) is released on DVD.
- Nov (1) "Buenos Aires" hits #3 on US Hot Dance Music/Club Play chart.
- (3) Madonna attends Marc Jacobs fashion show at the opening of New York City's 7th On 6th annual Fashion Week.
- (13) Madonna, Tina Turner and Courtney Love are photographed on the cover of Rolling Stone magazine's 30th anniversary issue.
- Dec (8) Madonna attends the Gianni Versace tribute at the Metropolitan Museum of Art's Costume Institute, Manhattan, NY.
    
1998
- Jan (7) Madonna begins filming "Frozen" video in the Mojave Desert, CA, directed by Chris Cunningham.
- (13) Madonna is #3 on Mr. Blackwell's 38th annual list of the worst-dressed women of 1997.
- (18) Madonna presents the award for Best Actor In A Motion Picture, Musical Or Comedy to Jack Nicholson in As Good As It Gets at the 55th annual Golden Globe Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
- Feb (14) Madonna performs a surprise mini-concert at 2:00 am to a sold-out crowd of 2,500 at The Roxy Club, New York, NY to promote her new CD Ray Of Light - it is her first club performance in 14 years.
- (16) "Frozen" video premieres on MTV.
- (17) Madonna arrives in London, England to begin her European promotional tour for Ray Of Light.
- (21) Madonna performs "Frozen" on BBC1-TV's National Lottery Show in London, England.
- (24) Madonna performs "Frozen" at the San Remo Song Festival in San Remo, Italy.
- (27) Madonna performs "Frozen" and is interviewed on TF1's Les Années Tubes TV show in Paris, France.
- (28) Madonna performs "Frozen" on Wetten Dass TV show in Duisberg, Germany.
- Mar (1) Inside Madonna TV special premieres on MTV.
- (2) Madonna completes her European promotional tour for Ray Of Light in Madrid, Spain.
- (3) Ray Of Light CD and "Frozen" single are released.
- (6) Madonna visits Toronto, ON, Canada to promote Ray Of Light: she attends a press conference at The Sutton Place Hotel and is interviewed live at 6:00 pm on MuchMusic TV.
- (10) "Don't Cry For Me Argentina" wins Favorite Song From A Movie (Evita) at the 4th annual Blockbuster Entertainment Awards at the Pantages Theatre, Los Angeles, CA.
- (13) Madonna guests and performs "Frozen" on NBC-TV's The Rosie O'Donnell Show.
- (15) Madonna attends the New York premiere of film Wide Awake (starring Rosie O'Donnell) at the Ziegfeld Theatre.
- (21) Ray Of Light hits US #2.
- (23) Madonna presents the Oscar for Best Original Song to James Horner and Will Jennings for "My Heart Will Go On" from Titanic at the 70th annual Academy Awards at the Shrine Auditorium, Los Angeles, CA.
- (24) Evita is released on DVD.
- (25) Madonna begins filming "Ray Of Light" video in Los Angeles, CA and New York, NY, directed by Jonas Akerlund.
- Apr (1) Madonna attends the premiere of film Mercury Rising in Beverly Hills, CA.
- (4) Madonna presents the Kids' Choice Blimp Award for favorite movie to Titanic and introduces a live performance by Cleopatra at the 11th annual Nickelodeon's Kids' Choice Awards at the UCLA Pauley Pavilion, Los Angeles, CA. "Frozen" hits US #2.
- (12) Madonna Rising TV special premieres on VH1.
- (22) Madonna attends the New York premiere party of film Two Girls And A Guy at the club Moomba. Ray Of Light is certified 2x platinum (2 million units).
- (27) Madonna performs "Frozen" with the East Harlem Violin Project at the 9th annual Rainforest Foundation Benefit Concert at Carnegie Hall, New York, NY, and also joins Elton John, Sting, James Taylor, Billy Joel, Herbie Hancock, Roberta Flack, Emmylou Harris and Joe Cocker in a rendition of The Beatles' "With A Little Help From My Friends" and "Twist & Shout".
- (28) Madonna attends the New York premiere of film Artemisia.
- (30) "Frozen" single is certified gold (500,000 units).
- May (8) Madonna is signed to co-star with Rupert Everett in Paramount Pictures film The Next Best Thing.
- (12) "Ray Of Light" video premieres on MTV.
- (18) "Don't Cry For Me Argentina" is honored as one of the Most Performed Songs Of 1997 at the 15th annual ASCAP Pop Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
- (21) Like A Virgin is certified 10x platinum (10 million units).
- (29) Madonna guests on CBS-TV's The Oprah Winfrey Show: she performs "Ray Of Light" and "Little Star".
- Jun (23) "Ray Of Light" single and video single are released.
- (25) Madonna begins filming "Drowned World/Substitute For Love" video in London, England, directed by Walter Stern.
- (30) Madonna - BIOrhythm TV special premieres on MTV.
- Jul (1) Madonna and Lourdes attend a Spice Girls concert at Madison Square Garden, New York, NY.
- (7) Madonna is the centre of a controversy when The London Daily Mirror accuses her of exploiting the late Princess Diana's tragic death in "Drowned World/Substitute For Love" video; a spokeswoman for Madonna releases a statement explaining that the video has nothing to do with Princess Diana and her life or her death.
- (11) "Ray Of Light" hits US #5. "Ray Of Light" video single hits US #4 on Top Music Videos chart.
- (25) "Drowned World/Substitute For Love" video premieres in Europe. "Ray Of Light" wins Video Of The Year at the 1998 VH1 Viewer's Vote Awards.
- Aug (1) Madonna is named VH1's Artist Of The Month.
- (8) Madonna begins filming "The Power Of Good-Bye" video in Los Angeles, CA, directed by Matthew Rolston.
- (12) Madonna is interviewed on ABC TV's Entertainment Tonight.
- (14) Madonna wins Best International Act at the German VIVA Comet Media Awards at the Akropolis in Cologne, Germany.
- (16) Madonna celebrates her 40th birthday. Madonna: Behind The Music documentary premieres on VH1.
- (24) "Drowned World/Substitute For Love" is released as a UK single.
- (25) Madonna reads the poem "Bittersweet" on Deepak Chopra's 2-CD set A Gift Of Love - Deepak & Friends Present Music Inspired By The Love Poems Of Rumi.
- (31) Madonna is interviewed on the set of "The Power Of Good-Bye" video on ABC-TV's Entertainment Tonight.
- Sep (5) "Drowned World/Substitute For Love" hits UK #10.
- (10) Madonna performs "Shanti/Ashtangi" and "Ray Of Light" at the 15th annual MTV Video Music Awards at the Universal Amphitheatre, Los Angeles, CA; "Ray Of Light" wins Best Video, Best Female Video, Best Direction, Best Choreography, Best Editing and "Frozen" wins Best Special Effects. "Ray Of Light" single is certified gold (500,000 units).
- (9,10) Madonna is featured in a 2-part interview on ABC-TV's Good Morning America.
- (11) "The Power Of Good-Bye" video premieres on MTV.
- (16) The World Vaishnava Association (WVA) condemns Madonna's performance of "Shanti/Ashtangi" at the MTV Video Music Awards on Sept 10 as sacrilegious in which she wore a holy facial marking and a see-through blouse. The New York Post announces that Madonna is dating 29-year-old British film director Guy Ritchie.
- (17) Madonna releases a statement against the WVA's criticism of her MTV performance: "The essence of purity and divinity is non-judgement… they should practice what they preach… if they're so pure, why are they watching MTV?"
- (24) Madonna accepts the Best International Video award for "Ray Of Light" via taped message at the 9th annual MuchMusic Video Awards at the Chumcity Building, Toronto, ON, Canada.
- (27) Madonna is guest of honor at the 14th annual AIDS Walk Los Angeles at Paramount Studios, Hollywood, CA.
- (28) Madonna narrates a chapter of "The Emperor's New Clothes" story on the Starbright Foundation benefit CD The Emperor's New Clothes: An All-Star Retelling Of The Classic Fairy Tale.
- (29) "The Power Of Good-Bye" single is released.
- Oct (15) Madonna is featured in book Ladies Home Journal's 100 Most Important Women Of The 21st Century.
- (21) Madonna presents the Man Of The Year Award to Sting at GQ's Men Of The Year Awards at Radio City Music Hall, New York.
- (22) "Borderline", "Papa Don't Preach", "True Blue" and "You Must Love Me" singles are certified gold (500,000 units).
- (23) Madonna performs "The Power Of Good-Bye" at the 4th annual VH1 Fashion Awards at the Theatre in Madison Square Garden, New York, NY; she is honored with the Gianni Versace Tribute Award and wins Most Fashionable Artist.
- (30) Madonna begins a European promotional tour for "The Power Of Good-Bye" single.
- Nov (1) Madonna makes a surprise appearance in London, England to present a lifetime achievement award to film director Alan Parker (Evita) at the Directors' Guild of Great Britain dinner in his honor on a boat on the River Thames.
- (7) Madonna performs "The Power Of Good-Bye" on Wetten Dass TV show in Linz, Austria.
- (9) Madonna is interviewed on NRJ Radio Show in Paris, France.
- (10) Madonna performs "The Power Of Good-Bye" and "Drowned World" on TF1's Les Années Tubes TV show in Paris, France.
- (12) Madonna performs "The Power Of Good-Bye" at the 5th annual MTV Europe Music Awards at the Fila Forum in Milan, Italy and wins 2 awards: Best Female and Best Album (Ray Of Light).
- (14) Madonna attends a press conference at the Grand Hotel in Stockholm, Sweden - her first visit to Sweden in 8 years.
- (15) Madonna performs "The Power Of Good-Bye" and is interviewed on Luuk TV show in Stockholm, Sweden.
- (17) Madonna performs "The Power Of Good-Bye" and "Drowned World" on El Septimo De Caballeria TV show in Madrid, Spain.
- (19) Madonna performs "The Power Of Good-Bye" on BBC1-TV's Top Of The Pops in London, England.
- (20) Madonna is interviewed by Johnny Vaughan on his BBC-TV show in London, England.
- (28) "The Power Of Good-Bye" hits US #11.
- Dec (6) Madonna narrates "The Camel Dances" story on animated HBO-TV special Rosie O'Donnell's Kids Are Punny.
- (7) Madonna congratulates Tony Bennett on his 50th anniversary in show business via taped message during his A&E-TV special Tony Bennett - Live By Request: An All-Star Tribute.
- (9) Madonna attends the 9th annual Fire & Ice Ball at Universal Studios, Los Angeles, CA.
- (11) Ray Of Light is certified 3x platinum (3 million units).
- (26) Madonna wins 2 Billboard Music Awards: Top Dance Club Play Artist and Top Dance Club Play Single ("Ray Of Light").
- (30) In Denmark, Madonna and Ray Of Light are named the most popular artist and album of 1998.
   
1999
- Jan (1) Madonna is voted Artist Of The Year by readers of the music internet website Rock On The Net.
- (4) Ray Of Light is voted Favorite Album Of The Year by Billboard magazine.
- (5) Madonna and Ray Of Light are nominated for 6 Grammy Awards: Album Of The Year, Record Of The Year, Best Pop Album, Best Dance Recording, Best Recording Package and Best Short-Form Music Video.
- (9) Madonna begins filming "Nothing Really Matters" video in New York, NY, directed by Johan Renck.
- (12) Madonna is #2 on Mr. Blackwell's 39th annual list of the worst-dressed women of 1998.
- (18) Madonna guests on CNN-TV's Larry King Live.
- (21) Madonna wins Best Female Artist and Best Dance/Electronica Artist in Rolling Stone magazine's 23rd annual Readers Poll.
- (29) Ray Of Light is voted Pop/Rock Album Of The Year by Playboy magazine.
- Feb (2) Madonna signs a long-term licensing and marketing contract with Sony Signatures: she will lend her name and image to fashion designers and manufacturers of fragrances, cosmetics and collectibles, and Swiss watchmaker Ebel.
- (5) Madonna is interviewed on ABC-TV's Entertainment Tonight.
- (6) Madonna wins Best International Female Artist and Best International Album (Ray Of Light) at the 10th annual Dansk Grammy Awards at Tivoli's Garden Concert Hall in Copenhagen, Denmark.
- (8) Madonna wins Female Artist Of The Year at the 1st annual NRJ Radio Awards at Cirkus in Stockholm, Sweden.
- (10) Madonna attends a reception at Astra in the D&D Building, New York, for the unveiling of Esquire magazine's March 1999 issue about the AIDS crisis in which she is featured on the cover with other AIDS activists.
- (13) "Nothing Really Matters" video premieres on MTV.
- (16) Madonna attends the Los Angeles premiere of Guy Ritchie film Lock, Stock And Two Smoking Barrels.
- (22) Max Factor announces a $6.5 million agreement with Madonna to collaborate on a line of several new cosmetic products, and she will also appear in TV commercials and ad campaigns which will run in Europe, Japan and Asia.
- (24) Madonna performs "Nothing Really Matters" at the 41st annual Grammy Awards at the Shrine Auditorium, Los Angeles, CA; Ray Of Light wins Best Pop Album, Best Dance Recording, Best Recording Package and Best Short-Form Music Video.
- Mar (2) Maverick Recording Company and Warner Bros. Inc. announce a long-term extension of their joint venture which also includes a new long-term contract with Maverick partners Madonna, Guy Oseary and Ronnie Dashev.
- (3) Madonna is voted Electronic Artist Of The Year and Ray Of Light is voted Electronic Album Of The Year in the 2nd annual Sonicnet / Addicted To Noise Readers Poll.
- (4) Madonna wins Best International Female Artist at the 39th annual Edison Music Awards in Amsterdam, Holland.
- (9) "Madonna - Ciao Italia: Live From Italy" (1988) is released on DVD.
- (15) Madonna is named one of People magazine's "25 Legends Of The Past 25 Years".
- (17) Madonna wins Best Dance Artist - Solo and Best Dance Video ("Ray Of Light") at the 14th annual International Dance Music Awards at the Winter Music Conference in Miami, FL.
- (19) Madonna attends Sony Music's pre-Academy Awards party at Mondrian Hotel's Asia de Cuba restaurant, Los Angeles, CA.
- (20) Madonna begins filming Max Factor commercial in Los Angeles, CA, directed by Alek Keshishian.
- (21) Madonna attends the Vanity Fair post-Academy Awards party at Morton's restaurant, West Hollywood, CA.
- (29) Evita: The Complete Motion Picture Music Soundtrack is certified 5x platinum (5 million units).
- Apr (5) Madonna is voted the Most Positive & Influential Sexual Voice Of The Past 35 Years in a USA Today online survey.
- (9) "Ray Of Light" wins Pop Video Of The Year and "Frozen" wins Best Special Effects In A Music Video at the 8th annual Music Video Production Association (MVPA) Awards at the Egyptian Theatre, Los Angeles, CA.
- (13) "Nothing Really Matters" single is released.
- (14) Ray Of Light wins Best Foreign Album Of The Year at the Fryderyk Music Awards in Warsaw, Poland.
- (20) Four Rooms (1995) is released on DVD.
- (23) Madonna begins filming The Next Best Thing, starring Rupert Everett and Benjamin Bratt, directed by John Schlesinger.
- (25) Madonna is featured in various photographs in The UK Sunday Times for the Max Factor campaign.
- (30) The Max Factor commercial premieres on TV in Europe.
- May (1) Madonna begins filming "Beautiful Stranger" video at Universal Studios, Los Angeles, CA, directed by Brett Ratner.
- (2) Madonna wins Best International Pop/Rock Album (Ray Of Light) and Best International Music Video ("Frozen") at the 6th annual Croatian Porin Music Awards in Makarska, Croatia.
- (8) "Nothing Really Matters" hits US #93.
- (11) Madonna & Ricky Martin duet "Cuidado Con Mi Corazon (Be Careful With My Heart)" is featured on his CD Ricky Martin.
- (13) Ray Of Light is named one of Rolling Stone magazine's "Essential Recordings Of The 90s".
- (17) "Frozen" is honored as one of the Most Performed Songs Of 1998 at the 16th annual ASCAP Pop Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
- (19) "Beautiful Stranger" video premieres on MTV. Madonna is interviewed by Charlie Rose on CBS-TV's 60 Minutes II.
- (23) Guinness Book of Records - Top 100 Singles includes "Crazy For You" #16 and "Holiday" #33.
- (26) "Ray Of Light" is honored as Top ASCAP Dance Song at the 12th annual ASCAP Rhythm & Soul Music Awards in the Hammerstein Ballroom at Manhattan Center, New York, NY.
- Jun (1) "Beautiful Stranger" single (from film Austin Powers: The Spy Who Shagged Me) is released.
- (8) "The Immaculate Collection" (1990) is released on DVD.
- (10) Madonna and Rupert Everett attend the Los Angeles premiere of his film An Ideal Husband.
- (16) Madonna is interviewed on ABC-TV's Entertainment Tonight.
- (29) Madonna files a $2.5 million lawsuit against her ex-financial advisors, Padell, Nadell, Fine, Weinberger & Co. for malpractice and breach of contract: she claims to have paid $2 million in New York state income taxes in 1992 after the firm prepared her taxes saying she was a California resident; Madonna seeks $2 million in compensatory damages and $500,000 in punitive damages.
- (30) Madonna completes filming The Next Best Thing in Los Angeles, CA.
- Jul (15) "Beautiful Stranger" is the most-played song on radio ever in UK: it was played 2,462 times in only one week.
- (17) During a 2-week vacation in Europe, Madonna attends the Versace Fashion Couture party at Man Ray Club in Paris, France.
- (24) "Beautiful Stranger" hits US #19.
- (26) "Beautiful Stranger" wins Best Pop Song Of The Year on BBC2-TV's Gaytime TV Awards in London, England.
- Aug (2) Madonna attends the Talk magazine launch party on Liberty Island, Manhattan, NY.
- Sep (9) Madonna wins Best Video From A Film for "Beautiful Stranger" and co-presents with Paul McCartney the Best Video Of The Year award to Lauryn Hill for "Doo Wop (That Thing)" at the 16th annual MTV Video Music Awards at the Metropolitan Opera House, New York, NY. (Madonna is crowned Most Honored Artist Of The 20th Century in the 15-year history of the MTV Video Music Awards with a career total of 18 awards).
- (12) Madonna and Lourdes attend the Versace Spring 2000 Show at the Roseland Ballroom, New York, NY.
- (30) "Blond Ambition Tour" is named The Greatest Concert Of The 1990s by Rolling Stone magazine.
- Oct (7) Madonna wins Favorite Female Artist at the 1st annual ARTIST Direct Online Music Awards in Los Angeles, CA.
- (13) Madonna attends the Details magazine party at the Metropolitan Pavilion, New York, NY.
- (17) Madonna receives death threats from a telephone caller on her way to London, England to begin work on a new album; upon their arrival at Heathrow Airport, Madonna and Lourdes are escorted by police but there are no incidents.
- Nov (1) Guinness World Records: Madonna is the most successful female solo artist for selling 120 million albums worldwide.
- (7) Madonna is #5 on "Top Entertainers Of The Half-Century (1950-2000)" list by Entertainment Weekly magazine.
- (9) "Madonna: The Video Collection 1993-99" is released on home video and DVD. Madonna is named Top-Selling Female Rock Artist Of The Century by the Recording Industry Association Of America (RIAA).
- (13) In UK, Madonna is voted Female Performer Of The Millenium on Channel 4's Music Of The Millenium Poll.
- (17) Madonna is voted Favorite Female Music Artist Of The 80s (37.8% votes) on AccessHollywood.com - Millenium Poll.
- (27) "Madonna: The Video Collection 1993-99" hits US #3 on Top Music Videos chart.
- (30) MTV & TV Guide's Top 100 Videos Ever Made includes "Vogue" #2, "Express Yourself" #10 and "Lucky Star" #50.
- Dec (1) Madonna is crowned Artist Of The Millenium by MTV Asia. Madonna is voted #3 Artist Of The Decade and "Beautiful Stranger" is #2 Song Of The Decade in RollingStone.com and TDK's "90s Music Time Capsule" Online Survey.
- (5) Madonna presents the Male Celebrity Style Award to Rupert Everett at the 5th annual VH1/Vogue Fashion Awards at the Lexington Avenue Armory, Manhattan, NY.
- (12) Madonna is #8 on The Detroit Free Press newspaper's "100 Greatest Artists & Entertainers Of Michigan's Century".
- (14) Madonna is voted Female Artist Of The Century by readers of SongLink International, a UK songwriters and music magazine.
- (18) Madonna is #3 on VH1-UK's "Millenium Honors List" of the top 100 greatest artists of the millenium.
- (25) Madonna is featured in Billboard magazine's "Totally 90s - Diary Of A Decade": Top Pop Artist Of The Decade #6, Top Pop Female Artist Of The Decade #4, Hot 100 Singles Of The Decade "Take A Bow" #24 and "Vogue" #93.
- (28) Madonna is honored as Female Artist Of The Millenium by Radio Tel Aviv in Israel.
- (30) In Australia, Madonna is voted #1 "Female Music Star Of The Millenium" in a Virtual Time Capsule by 2DayFM radio station.
- (31) MuchMusic: Top 100 Videos Of The Century includes "Express Yourself" #3, "Ray Of Light" #8 and "Like A Prayer" #47.
   
2000

- Jan (1) Madonna and Guy Ritchie celebrate the new millenium at Donatella Versace's party at the Versace Mansion in Miami, FL.
- (3) In Israel, Madonna is named Female Artist Of The Decade by listeners of Galgalatz radio station.
- (4) Madonna is nominated for 2 Grammy Awards: Best Female Pop Vocal Performance and Best Song Written For A Motion Picture, Television Or Other Visual Media ("Beautiful Stranger").
- (10) Madonna begins filming "American Pie" video in London, England, directed by Phillip Stolzl.
- (14) "Beautiful Stranger" wins Best Song at the 3rd annual Las Vegas Film Critics Society Awards in Las Vegas, NV.
- (18) "Beautiful Stranger" is named the most-played song on UK radio in the year 1999: it was played 44,483 times to an audience of 1,468,204 radio listeners which makes Madonna the first female solo artist to top the Radio Airplay chart in England.
- Feb (2) Madonna is interviewed on ABC-TV's Entertainment Tonight.
- (4) Madonna and Benjamin Bratt (co-star of The Next Best Thing) guest on NBC-TV's The Rosie O'Donnell Show.
- (5) Madonna is a special guest at the 27th annual Evening Standard British Film Awards at the Savoy Hotel, London, England.
- (11) "American Pie" video premieres on MTV.
- (14) Madonna attends the London premiere of film The Talented Mr. Ripley at the Empire Theatre, Leicester Square.
- (22) The Next Best Thing: Music From The Motion Picture soundtrack CD is released and includes 2 new songs by Madonna: "American Pie" (a remake of 1971 Don McLean classic) and "Time Stood Still".
- (23) "Beautiful Stranger" wins Best Song Written For A Motion Picture, Television Or Other Visual Media at the 42nd annual Grammy Awards at the Staples Center, Los Angeles, CA.
- (26) MTV - Top 25 Most Played Music Videos includes "Like A Virgin" #8 and "Vogue" #18.
- (28) "American Pie" single (from The Next Best Thing) is released.
- (29) Madonna and Guy Ritchie attend the New York premiere of The Next Best Thing at the Loews Cineplex Theatre. Madonna Exposed - The Next Best Thing Movie Special premieres on VH1.
- Mar (1) Madonna guests on MTV's Total Request Live (TRL) at the MTV Building in Times Square, New York, NY.
- (2,3) Madonna is interviewed by Matt Lauer on NBC-TV's Today.
- (3) The Next Best Thing is released nationwide. Madonna is featured in an interview on MTV's Fanatic.
- (4) "American Pie" hits US #29.
- (5) The Next Best Thing hits #2 at the US box-office with $5.8 million on its opening weekend.
- (16) The Immaculate Collection is certified 9x platinum (9 million units), Ray Of Light is certified 4x platinum (4 million units).
- (20) Madonna announces she is 3-months pregnant with her second child and the father is Guy Ritchie.
- (23) Madonna and Guy attend the re-opening of the Tate Britain Gallery, London, England.
- (25) Madonna wins a Razzie Award for Worst Actress Of The Century at the 20th annual Golden Raspberry Awards at the Hollywood Roosevelt Hotel Academy Room, Los Angeles, CA.
- Apr (7) "Beautiful Stranger" wins Best Cinematography In A Music Video at the 9th annual Music Video Production Association (MVPA) Awards at the Directors Guild of America, Los Angeles, CA.
- (20) Madonna begins filming "Music" video in Los Angeles, CA, directed by Jonas Akerlund.
- (25) "Beautiful Stranger" is honored as one of the Most Performed Songs From A Motion Picture at the 15th annual ASCAP Film & Television Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
- May (21) The Next Best Thing has grossed a total of $14.9 million US at the box-office.
- (25) "Beautiful Stranger" wins PRS (Performing Rights Society) Most Performed Work at the 45th annual Ivor Novello Awards at the Grosvenor House Hotel in London, England.
- (31) A copy of Madonna's new single "Music" is illegally downloaded on the internet by Napster months before its release date and her record company is threatening legal action.
- Jun (1) Madonna attends a charity dinner hosted by HRH Prince Charles at his Highgrove estate in Gloucestershire, England.
- (6) Madonna attends the London premiere of The Next Best Thing at the Odeon West End Theatre, Leicester Square.
- (7) "Nothing Really Matters" is honored as one of the Most Performed Dance Songs Of 1999 at the 13th annual ASCAP Rhythm & Soul Music Awards in the Hammerstein Ballroom at Manhattan Center, New York, NY.
- (13) Desperately Seeking Susan (1985) is released on DVD.
- (18) In Singapore, Madonna is named Best Female Artist at the 1st annual Radio Music Awards at the Harbour Pavilion.
- Aug (1) The official website www.MadonnaMusic.com is launched by Warner Bros Records.
- (2) "Music" video premieres on MTV.
- (11) Madonna gives birth to a 5-lb, 9-oz boy, Rocco Ritchie, at 11:59 am at Cedars-Sinai Medical Centre, Los Angeles, CA.
- (22) "Music" single is released.
- (24) Madonna files a complaint with the World Intellectual Property Organization (WIPO) of the United Nations for ownership of the internet address www.madonna.com, a pornographic website presently owned by New Jersey entrepreneur Dan Parisi.
- (26) Madonna becomes the first female solo artist to have 10 No. 1 singles in UK with "Music".
- (29) The Next Best Thing is released on home video and DVD.
- Sep (5) "Music" DVD video single is released.
- (16) "Music" hits US #1 for four consecutive weeks - it is her 12th No. 1 and 33rd Top 10 single in US.
- (18) Madonna participates in her first live online chat on America Online (AOL).
- (19) Music CD is released. Madonna attends the Music launch party at the club Catch One, Los Angeles, CA.
- (22) Madonna makes a surprise in-store appearance at the Virgin Megastore, West Hollywood, CA, to sign copies of Music CD.
- (23) "Music" DVD hits US #3 on Top Music Videos chart.
- (24) Music has sold 420,000 US copies in one week and hits #1 in 23 countries such as: Austria, Brazil, Canada, Czech Republic, Denmark, Finland, France, Germany, Greece, Holland, Hungary, Ireland, Italy, Norway, Poland, Sweden, Switzerland, UK, US.
- (26) Madonna announces she will perform mini-concerts in New York and London clubs in Nov 2000.
- Oct (3) Madonna is certified 5x platinum (5 million units), Something To Remember is certified 3x platinum (3 million units).
- (7) Music hits US #1 for one week - her first No. 1 album in 11 years.
- (10) VH1 - 100 Greatest Dance Songs includes "Vogue" #4 and "Into The Groove" #40.
- (16) Madonna wins her case for ownership of the internet address www.madonna.com and the World Intellectual Property Organization orders businessman Dan Parisi to transfer the site back to her.
- (17) Madonna begins filming "Don't Tell Me" video in Los Angeles, CA, directed by Jean-Baptiste Mondino.
- (24) Madonna contributes "Shanti/Ashtangi" to all-star Tibetan benefit CD Mantra Mix.
- (25) Music is certified 2x platinum (2 million units), "Music" single is certified 1x platinum (1 million units).
- (26) RIAA Top Selling Artists: Madonna is #10 with 57 million certified units in US.
- Nov (1) Guinness World Records: Madonna is the most successful female solo artist for selling 130 million records (singles and albums) and having 35 Top 10 singles and 12 Top 10 albums in US with a UK total of 47 Top 10 singles and 14 Top 10 albums.
- (3) Madonna guests and performs "Don't Tell Me" on CBS-TV's Late Show With David Letterman.
- (5) Madonna performs a mini-concert at the Roseland Ballroom, New York, NY.
- (7) Madonna announces she will perform at Brixton Academy, London on Nov 28 - her first UK concert in 7 years.
- (10) "Music" wins Best Pop Clip Of The Year at the 22nd annual Billboard Video Awards at the Universal Hilton, Los Angeles, CA.
- (11) Madonna guests and performs "Don't Tell Me" on Wetten Dass TV show in Freiburg, Germany.
- (12) Madonna is interviewed on CNN-TV's World Beat.
- (13) Madonna is named Best International Female Artist at the 4th annual Premios Amigo Awards in Madrid, Spain.
- (16) Madonna performs "Music" at the 7th annual MTV Europe Music Awards at the Globe Arena in Stockholm, Sweden and wins 2 awards: Best Female and Best Dance Act.
- (17) "Don't Tell Me" video world premieres on BBC1-TV's Top Of The Pops in London, England.
- (18) Madonna is interviewed on NRJ Radio Show at the Champs Elysées in Paris, France.
- (19) Madonna performs "Music" and "Don't Tell Me" and is interviewed on Nulle Part Ailleurs TV show in Paris, France.
- (20) Madonna is interviewed on TF1's Journal de 20 Heures in Paris, France.
- (24) Madonna performs "Don't Tell Me" on BBC1-TV's Top Of The Pops in London, England.
- (25) Rolling Stone & MTV: The 100 Greatest Pop Songs includes "Like A Virgin" #4, "Vogue" #19 and "Papa Don't Preach" #62.
- (27) "Don't Tell Me" video premieres on VH1.
- (28) Madonna performs a mini-concert at Brixton Academy, London, England, which is webcast live on the internet on Microsoft Network (MSN) at 8:00 pm GMT and seen by 9 million viewers in UK, US and Europe - it is the biggest live webcast ever and breaks the record of 3 million set by Paul McCartney's online concert at Liverpool's The Cavern Club in 1999.
- (30) In UK, Madonna's house is burglarized while she and her family are asleep: reports confirm that thieves stole her boyfriend's Range Rover and various other items; the vehicle is recovered and the matter is being investigated by police.
- Dec (2) Madonna performs "Don't Tell Me" on Carramba Che Fortuna TV show in Rome, Italy.
- (7) Madonna announces her engagement to Guy Ritchie and that they will marry in Scotland on Dec 22, 2000.
- (15) Madonna purchases an $8 million estate in London, England. "Music" is named Single Of The Year by People magazine.
- (17) "Music" is voted Best Pop Single and Best Pop Album in Dotmusic.com Records Of The Year Readers Poll.
- (18) Madonna and her family arrive in Scotland to begin wedding preparations; upon her arrival at Inverness Airport, she is greeted by journalists, fans and a bagpiper who welcomes her with a rendition of "Like A Virgin".
- (21) Rocco Ritchie is baptized at Dornoch Cathedral, Dornoch, Scotland.
- (22) Madonna and Guy Ritchie are married at Skibo Castle in Dornoch, Sutherland, Scotland with Gwyneth Paltrow, Stella McCartney, Sting, George Clooney, Jon Bon Jovi, Celine Dion, Bryan Adams, Rupert Everett and others in attendance.
- (23) Madonna and Guy leave Scotland for their honeymoon: it is reported that they will spend Christmas with Sting and his wife Trudi Styler at their holiday-weekend estate in Wiltshire, England.
- (25) Madonna performs "Music" on a special Christmas episode of BBC1-TV's Top Of The Pops in London, England.
- (29) Madonna is named Woman Of The Year, Hype Of The Year (Madonna at Brixton) and "Music" is named Best Promo Video Of The Year by the writers of Dotmusic.com.
- (30) Madonna wins Top Hot Dance Club Play Artist, Top Hot Dance Club Play Single ("Music") and Top Hot Dance Maxi-Singles Sales ("Music") in Billboard magazine's The Year In Music survey.
 
2001
- Jan (3) Madonna is nominated for 4 Grammy Awards: Record Of The Year, Best Female Pop Vocal Performance ("Music"), Best Pop Vocal Album and Best Recording Package (Music).
- (4) VH1 - 100 Greatest Albums Of Rock N Roll includes Like A Prayer at #100.
- (9) Madonna contributes "Lucky Star" (1984) to Snatch: Original Motion Picture Soundtrack CD. Madonna is #4 on Mr. Blackwell's 41st annual list of the worst-dressed women of 2000.
- (14) In Canada, "Music" and "American Pie" are named the No. 1 and No. 2 Top Singles Of The Year 2000 - it is the first time in Canadian chart history that an artist holds both the top 2 positions on the year-end music charts.
- (16) "Don't Tell Me" single (which includes a bonus CD-ROM video) is released.
- (18) Madonna and Guy attend the Los Angeles premiere of his film Snatch at the Directors Guild of America. Madonna wins Best Single ("Music"), Best Video ("Music") and Best-Dressed Artist in Rolling Stone magazine's 25th annual Readers Poll.
- (20) Madonna wins Best International Female Artist and Best International Album (Music) at the 2nd annual NRJ Music Awards at the Midem Music Conference, Palais des Festivals in Cannes, France.
- Feb (3) "Don't Tell Me" hits US #4 - it is her 34th Top 10 US single and surpasses The Beatles to become the second artist behind Elvis Presley with the most Top 10 hits on the US charts.
- (7) Madonna is named Best International Female Artist at the 3rd annual NRJ Radio Awards in Heron City, Stockholm, Sweden.
- (11) Madonna begins filming "What It Feels Like For A Girl" video in Los Angeles, CA, directed by Guy Ritchie.
- (18) Madonna writes a letter to the Los Angeles Times newspaper in defense of controversial rap artist Eminem over the public and media criticism of his offensive song lyrics and Grammy Award nominations: "What is the big deal about Eminem? Since when is offensive language a reason for being unpopular? I find the language of George W. much more offensive. I find the hypocritical nature of most popular figures in our culture much more offensive. I like the fact that Eminem is brash and angry and politically incorrect. At least he has an opinion. He's stirring things up, he's provoking a discussion, he's making people's blood boil. He's reflecting what's going on in society right now. That is what art is supposed to do. And after all he's just a boy. Thank God he's rebellious and not well-groomed. He gets my vote. Yours truly, Mrs. Ritchie".
- (21) Madonna performs "Music" at the 43rd annual Grammy Award
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