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Celebrating Madonna: The Queen of Pop’s 50 Most Iconic Moments

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Madonna's 50 Most Memorable Moments: 1984 STYLE bracelets

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The Queen of Pop's 50 Most Iconic Moments

Madonna's 50 Most Memorable Moments: 1985: Penthouse and Playboy Covers

Madonna on Penthouse and Playboy Covers (1985)

When: July 1985
What: Capitalizing on her rising fame, both Playboy and Penthouse unearthed nude black-and-white photos of Madonna taken in 1978, when she earned money as an artists' model. Madonna was paid only $30-$50 per session when the shots were snapped, and couldn't prevent their publication. Both magazines greatly increased their print runs to satisfy demand, and Madonna refused to give in to the media frenzy and remained uncharacteristically mum. A New York Post headline at the time screamed, "Madonna: 'I'm not ashamed.'"

Madonna's 50 Most Memorable Moments: 1986: Sean Penn

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Madonna Marries Sean Penn (1985)

When: 1985
What: Madonna got married for the first time – to actor Sean Penn, who she met on the set of her "Material Girl" video – on her 27th birthday. A year later, the pair starred in the ill-fated film Shangai Surprise. But one of them loved the spotlight and the other shunned it, and their stormy relationship ended in divorce in January 1989.

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Weird Al’s ‘Like a Surgeon’ (1985)

When: 1985
What: "Weird Al" Yankovic remade "Like a Virgin" as "Like a Surgeon," putting Madonna in the same league as the also-mimicked Michael Jackson. Legend has it Madonna actually suggested the idea, and after it got back to "Weird Al," he decided to act on the tip.

Madonna's 50 Most Memorable Moments: 1986: True Blue

Photograph by Herb Ritts

Madonna’s ‘True Blue’ (1986)

When: 1986
What: Madonna's True Blue album cover was shot by esteemed photographer Herb Ritts as she cemented her relationship with high-power visual artists. Ritts would go on to direct her 1989 video for "Cherish" as well as shoot Rolling Stone's September 10, 1987 Madonna cover.

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‘Papa Don’t Preach’ Video (1986)

When: June 11, 1986
What: Released "Papa Don't Preach" as a single, which set off a firestorm of debate over whether Madonna was pushing a pro- or anti-abortion agenda – or taunting the Pope. After she dedicated the tune to Pope John Paul II, the Catholic leader instructed fans to boycott her 1987 Who's That Girl Tour.

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Madonna’s First Letterman Appearance (1988)

When:July 1988
What: Tried to convince the world she was having a lesbian affair with actress Sandra Bernhard. Madonna has always loved to play with sexual boundaries, and she had a ball on an episode of David Letterman's show when she and Bernhard pronounced "I love you" to each other while wearing matching jean shorts and white T-shirts. "We hook up, sometimes with Jennifer Grey," Bernhard said during the provocative interview, Madonna's first of many appearances on Letterman.

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‘Like a Prayer’ Video (1989)

When: 1989
What: Madonna's scandalous video for "Like a Prayer" – featuring the star dancing in a field of burning crosses, plus simulated stigmata and interracial relationships – derailed her lucrative deal with Pepsi. Once the video premiered, the soda maker nixed their agreement to use the song in a commercial and yanked the money they had committed to supporting her Blond Ambition tour. The video became one of the singer's most iconic small-screen moments.

Madonna's 50 Most Memorable Moments: 1990: Blond Ambition

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‘Blond Ambition’ Tour (1990)

When: April 12, 1990
What: On the first date of her Blond Ambition Tour, Madonna unveiled what would become one of the most signature wardrobe selections in rock history: the cone bra. The undergarment (employed by Madonna as an over-garment) was designed by Jean-Paul Gaultier and worn during the opening part of the show, when Madonna hit the stage with "Express Yourself."

Madonna's 50 Most Memorable Moments: 1990: Masturbation

Photo: Preston/Corbis

‘Blond Ambition’ Tour (1990)

When: April through August 1990
What: Madonna's Blond Ambition Tour also saw the debut of one of her most famous onstage moves: simulating masturbation on a bed to "Like a Virgin." The extremely sexual nature of the show got it banned — notably in Rome, after the Pope called for a boycott. Police threatened to shut down the tour in Toronto, but Madonna performed without legal trouble.

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‘Justify My Love’ Video (1990)

When: 1990
What: "Justify My Love" became Madonna's first video to be banned from MTV. The song, off hits compilation The Immaculate Collection, was co-written by Madonna, Lenny Kravitz and Ingrid Chavez. The track was definitely salacious, but its video – which starred Madonna's then-boyfriend Tony Ward – stirred up the most controversy with its simulated sex and bondage scenes. The clip was shot like an arty sex film and actually debuted on ABC's Nightline, after which it was sold as a video single.

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Madonna In ‘Dick Tracy’ (1990)

When: 1990
What: Teamed with then-beau Warren Beatty in a big-screen adaptation of comic strip Dick Tracy. Madonna played blond bombshell Breathless Mahoney and performed "Sooner or Later" at the Oscars, where it received the prize for Best Original Song. Madonna released I'm Breathless (Music From Dick Tracy) that year, which included collaborations with Stephen Sondheim.

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‘Vogue’ (1990)

When: 1990
What: "Vogue" was a song off Madonna's I'm Breathless but its influence was felt far beyond her Dick Tracy role. The Shep Pettibone-produced track brought the gay dance craze to the mainstream, and had an entire generation mimicking the arm-waving choreography from David Fincher's music video. Madonna adapted a version of the dance for MTV's VMAs, which she performed in full Victorian garb on September 6, 1990.

Madonna's 50 Most Memorable Moments: 1991: Truth or Dare

‘Truth or Dare’ Documentary (1991)

When: October 9, 1991
What: Madonna released tour documentary Truth or Dare, which featured footage from her Blond Ambition shows mixed with offstage scenes that aimed to depict her close relationships with her dancers and hectic, complex life. The star bickers with Warren Beatty onscreen, makes an emotional visit to her hometown, and concludes the tour by crawling in bed with all her dancers for some final bonding time. The film's most famous scene features Madonna deep-throating a bottle during a game of Truth or Dare.

Madonna's 50 Most Memorable Moments: 1992: (VIDEO) Erotica Sex Book

‘Erotica’ Sex Book (1992)

When: October 21, 1992
What: Released her Sex book, a coffee-table title that pictured Madonna in a variety of Rated-R positions alongside Vanilla Ice, Naomi Campbell and Big Daddy Kane, among others. The majority of the photographs were credited to Steven Meisel, and the book's limited run sold out in days. Madonna released the book in tandem with Erotica, a concept record about sexuality that earned a Parental Advisory sticker and furious public debate.

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‘A League of Their Own’ (1992)

When: 1992
What: Madonna returned to the big screen alongside Rosie O'Donnell and Geena Davis in A League of Their Own, a fictional story based on the real women's baseball league that cropped up during World War II when many male players went off to war. Madonna portrayed "All the Way" Mae Mordabito, a tough-talking center fielder with a taste for men. She contributed ballad "This Used to Be My Playground" to the film's soundtrack.

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Madonna Appears on SNL (1992)

When: 1992
What: Perhaps rehearsing for her later interest in the Jewish mysticism Kabbalah, Madonna was "like buttah" on "Coffee Talk," kvelling over Barbra Streisand on Saturday Night Live alongside Mike Myers. She portrayed "Liz Rosenberg" (the name of her longtime publicist) alongside Roseanne. Two years earlier, Madonna thrilled Wayne and Garth with a special SNL cameo.

Madonna's 50 Most Memorable Moments:(1993)Girlie Show controversy with Puerto Rican flag

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‘Girlie Show’ Tour Controversy (1993)

When: August 25, 1993 – December 19, 1993
What: Unsurprisingly, Madonna's Girlie Show Tour – featuring songs from Erotica – met some controversy. But it wasn't the stripping and simulated orgies that had Puerto Rican fans in a fury: Madonna rubbed the nation's flag between her legs onstage during her performance there.

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Madonna on Letterman (1994)

When: March 31, 1994
What: If Madonna didn't set a record for number of times a guest used the word "fuck" during a David Letterman appearance in 1994, she sure came close. The two sniped at each other in an extremely awkward interview that would go down in infamy.