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.

Read more of Madonna's Career Diary...