1988
- an 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.
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