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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: Desperately Seeking Susan

Photograph by Herb Ritts

Madonna in ‘Desperately Seeking Susan’ (1985)

When: May 9, 1985
What: Returned to the cover of Rolling Stone to promote her new film Desperately Seeking Susan with costar Rosanna Arquette. Madonna's first foray onto the big screen was pretty smooth: the film about a suburban housewife who gets mixed up in the seamy New York underworld earned a Golden Globe nomination, and Madonna's "Into the Groove" appeared on the movie's soundtrack. " 'Into the Groove' is another song I feel retarded singing," she admits to RS now, "but everybody seems to like it."

Madonna's 50 Most Memorable Moments: 1985: Like a Virgin tour

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‘Like a Virgin’ Tour’ (1985)

When: April through June 1985
What: Madonna surprised North American cities with the Virgin Tour, which featured newcomers the Beastie Boys as her opening act. The tour set the tone for Madonna's future treks: frequent costume changes (including "Like a Virgin"-style wedding gowns), big dance numbers and an interpolation of a contemporary's tune (in this case, Michael Jackson's "Billie Jean").

Madonna's 50 Most Memorable Moments: 1985: Live Aid

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Live Aid (1985)

When: July 13, 1985
What: Madonna showed that her seemingly light-hearted pop had a humanitarian side by taking the stage to perform "Holiday," "Into the Groove" and "Love Makes the World Go Round" at Philadelphia's JFK Stadium as part of the Live Aid concerts that raised money to fight famine in Ethiopia. The Thompson Twins and Nile Rodgers joined her for the final song, and Madonna was introduced by Bette Midler.

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

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‘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.

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Courtney Love Crashes Madonna’s VMA Interview (1995)

When: September 7, 1995
What: Madonna's chat with MTV's Kurt Loder outside the Video Music Awards got crashed by another blond who loves the spotlight – Courtney Love. "No, don't, please," Madonna said when Loder started to invite the Hole singer in to the interview.

Madonna's 50 Most Memorable Moments: 1996: Lourdes is born

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Lourdes Is Born (1996)

When: October 14, 1996
What: Madonna gave birth for the first time to Lourdes, her daughter with personal trainer Carlos Leon. Becoming a mother had a profound effect on Madonna, who lost her own mom to cancer at age six, and many songs on 1998's Ray of Light reflected her new perspective.

Madonna's 50 Most Memorable Moments: 1997: EVITA Golden Globe

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Madonna Wins Golden Globe for ‘Evita’ (1996)

When: December 25, 1996
What: Evita was released. The film, which starred Madonna as Eva Peron, was her best-received onscreen performance, earning her a Golden Globe for Best Performance by an Actress in a Motion Picture; her song, "You Must Love Me," scored an Oscar. Madonna underwent significant vocal training for the role, which she credited with strengthening her voice on subsequent albums.

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Madonna Sings on ‘Austin Powers’ Soundtrack (1999)

When: 1999
What: Madonna teamed with the hottest English spy on the big screen for the Austin Powers soundtrack song "Beautiful Stranger."

Madonna's 50 Most Memorable Moments: 2000: Guy Ritchie (Rocco) (2000)

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Madonna Marries Guy Ritchie (2000)

When: 2000
What: In 1999, Madonna's close friends Sting and Trudie Styler introduced her to British director Guy Ritchie at a dinner party. A year later, she and Ritchie had a son, Rocco, and married at a lavish ceremony at a Scottish castle. After months of tabloid speculation, the pair split in October 2008 and were officially divorced in December.

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‘Music’ Video (2000)

When: 2000
What: Madonna demonstrated her ability to sniff out up-and-coming talent when she cast British comic Sacha Baron Cohen (in his guise as a clueless hip-hopper Ali G) in her video for "Music."

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‘What It Feels Like For a Girl’ Video (2001)

When: 2001
What: Madonna's video for "What It Feels Like for a Girl," a warm, throbbing track from Music, was banned from MTV for what the network deemed excessive violence. Guy Ritchie directed the clip, which depicts the singer as a dangerous car thief who goes on a tear of destruction before killing herself and her elderly passenger.

Madonna's 50 Most Memorable Moments: 2001: Drown World Guitar

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‘Drowned World Tour’ (2001)

When: June 9, 2001
What: Debuted her new guitar skills on the first date of her Drowned World Tour. The trek, Madonna's first world tour since 1993's Girlie Show, was broken into themed segments that explored English punk, the Asian geisha craze, western style, Latin flamenco and urban funk. She picked up a black electric guitar for the first time onstage (her touring guitarist, Monte Pittman, taught her the ropes) and plucked an acoustic six-string, as well.

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‘Swept Away’ Trailer (2002)

When: October 11, 2002
What: Madonna and Guy Ritchie teamed up for the ill-advised Swept Away, a big-screen bomb that became one of the year's biggest pop culture punch lines. The remake of an Italian flick from the '70s hit all the wrong notes, depicting the singer as a bratty rich housewife who gets stranded on a remote island with a hunky member of her ship's crew.

Madonna's 50 Most Memorable Moments: 2003: Author English Roses

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Madonna Writes ‘The English Roses’ (2003)

When: 2003
What: Madonna showed off more of her nurturing side by authoring her first in a series of children's books called The English Roses


Madonna's 50 Most Memorable Moments: 2003: Madonna Britney kiss VMA

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Madonna Kisses Britney Spears (2003)

When: September 13, 2003
What: Madonna passed the torch to younger pop sensations Britney Spears and Christina Aguilera – with her lips – at MTV's Video Music Awards. After the three sang "Like a Virgin" together, Madonna kissed the two starlets, then Missy Elliott jumped onstage and the quartet performed "Hollywood" while the stunned audience (including Britney's recent ex, Justin Timberlake) stared in shock.

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Madonna Performs with Britney Spears (2003)

When: 2003
What: Appeared in Britney Spears' video for "Me Against the Music." Madonna had been spotted out and about wearing a Britney Spears T-shirt, and she brought her fandom to a new level by lending her dancing to Spears' clip. After the younger star's very public meltdown, Madonna again showed her support by putting Spears in one of the video clips that ran during her Sticky & Sweet Tour, and inviting Britney to join her onstage at a November 2008 concert in Los Angeles.

Madonna's 50 Most Memorable Moments: 2004: Kabbahlah

Photos: Rawlings/Kabbalah Center Israel

Kabbalah (2004)

When: June 2004
What: Madonna's devotion to Kabbalah reached a new height as she announced she had adopted the Hebrew name Esther.

Madonna's 50 Most Memorable Moments: 2005: Horse accident

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Madonna Suffers From Horse Accident (2005)

When: August 2005
What: Madonna posed as the lady of her English manor with her husband and children for the August issue of Vogue, but her relationship with horses got a little more complicated after she was thrown from one on the grounds of her Ashcombe estate. She suffered cracked ribs, a broken collarbone and a broken hand in the accident; she rode again for the first time during an October episode of David Letterman's show, and incorporated horse imagery into her 2006 Confessions Tour. She was thrown again in 2009 while riding in the Hamptons, and placed the blame on nearby paparazzi photographers spooking the animal.

Madonna's 50 Most Memorable Moments: 2006: Madonna on cross

Photo: Mazur / Wireimage

‘Confessions Tour’ (2006)

When: May 21, 2006
What: The image of the crucifix has always played a role in Madonna's art, and she racked up controversy once again on her Confessions Tour by performing "Live to Tell" while suspended from a giant glittery cross. She explained the number as a commentary on the devastation of AIDS in Africa.

Madonna's 50 Most Memorable Moments: 2006: David Banda

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Madonna Adopts David Banda (2006)

When: October 2006
What: Madonna traveled to Malawi and filed papers to adopt a boy she found in an orphanage there named David Banda. The seemingly selfless gesture still attracted criticism: Madonna found her actions questioned after it came to light that David wasn't exactly an orphan (he had a father who at first contested the adoption), and that Malawi had laws requiring residency in the nation before an adopted child could be moved. The adoption wasn't finalized until May 2008. Madonna also started a foundation called Raising Malawi and made a documentary about the plight of the country's orphans called I Am Because We Are.

Madonna's 50 Most Memorable Moments: 2008: Hall of Fame

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Rock and Roll Hall of Fame Induction (2008)

When: March 10, 2008
What: Madonna entered the Rock and Roll Hall of Fame. Fellow Michigan native Iggy Pop and the Stooges performed her "Burning Up" and "Ray of Light" at the ceremony, and Justin Timberlake inducted her with a light-hearted speech in which he recalled the star giving him a B-12 shot: "That's what Madonna was and will continue to be for all of us: A shot in the ass when we need it most," Timberlake said.

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‘4 Minutes’ Video (2008)

When: April 2008
What: Madonna hooked up with Justin Timberlake for "4 Minutes," the first video from Hard Candy. Though she often worked with under-the-radar producers and underground dance DJs, Madonna teamed with Timberlake, Timbaland and Pharrell on the album, which saw her exploring a more urban-disco sound.

Madonna's 50 Most Memorable Moments: 2009: Celebration lourdes

Lourdes Films ‘Celebration’ Video (2009)

When: September 1, 2009
What: Madonna watched her eldest daughter morph into her Eighties self. On the set of the video for "Celebration," Lourdes dressed up in Madonna's "Like a Virgin" get-up with jaw-dropping results.

Madonna's 50 Most Memorable Moments: 2009: Sticky and sweet

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‘Sticky & Sweet’ Tour (2009)

When: September 2, 2009
What: Madonna broke her own record as her Sticky & Sweet trek wrapped after 85 shows: $408 million grossed, more than 3.5 million fans attended and 32 countries hit, according to Live Nation, the tour's producer.

Madonna's 50 Most Memorable Moments: 2009: MJ tribute

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Michael Jackson VMA Tribute (2009)

When: September 13, 2009
What: Surprised the crowd at MTV's VMAs in New York by taking the stage as the show opened and delivering an emotional, sobering speech about Michael Jackson and his relationship to herself and fame.

Madonna's 50 Most Memorable Moments: 2009: SNL with GAGA

Photo: Edelson/NBC

‘Saturday Night Live’ with Lady Gaga (2009)

When: October 3, 2009
What: Made a cameo alongside Lady Gaga on Saturday Night Live and convincingly play-fought with her newest protégé while trading barbs like, "What the hell is a disco stick?!"

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