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").