Since moving to New York City with just a few dollars in her pocket up until the release of her 13th studio album Rebel Heart this year, Madonna has inspired countless fans, confounded expectations and never failed to entertain along the way. From her first top 10 hit on the Hot 100 to her f-bomb-laden Letterman appearance to her directorial debut, here are 33 of Madonna’s career highlights.
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1978
Image Credit: Michael McDonnell/Hulton Archive/Getty Images In 1978, Michigan-born Madonna Louise Ciccone dropped out of college and moved to New York City to pursue a career in dance.
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1982
Madonna released “Everybody,” her debut single, on Sire on Oct. 6, 1982. The 24-year-old singer wasn’t pictured on the single artwork, reportedly because the label wanted to market the song to an African-American audience.
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1983
Image Credit: Courtesy Photo On July 27, 1983, Madonna released her self-titled debut on Sire. It debuted at No. 190 on the Billboard 200, peaking at No. 8 in 1984. She wrote five of the album’s eight tracks, including “Burning Up” and “Lucky Star.”
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1983
Image Credit: Courtesy Photo “Borderline,” one of two Madonna tracks written by album producer Reggie Lucas, became Madonna’s first top 10 single on the Billboard Hot 100. The fifth single from her first album, the track peaked at No. 10.
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1984
Image Credit: Richard Corkery/NY Daily News Archive via Getty Images In what many now consider a career-making performance, Madonna performed at the first-ever MTV VMAs in 1984. Singing “Like a Virgin” in a wedding dress while gyrating and writhing suggestively on the floor, Madonna scandalized many and captured the attention of everyone. “Like a Virgin” became her first No. 1 single on the Hot 100 and No. 1 album on the Billboard 200.
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1985
Image Credit: Orion/Everett Collection Madonna starred alongside Rosanna Arquette in Desperately Seeking Susan, which opened on March 29, 1985. Playing a carefree version of herself, Madonna’s fashion in the film (and “Into the Groove”) made a huge impression on pop culture.
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1985
Image Credit: Frank Micelotta/ImageDirect In April of 1985, Madonna kicked off The Virgin Tour, her first North American tour. Her opening act? The Beastie Boys.
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1985
Image Credit: Laura Luongo/Liaison Madonna started dating actor Sean Penn (then best known for his role in Fast Times at Ridgemont High) while filming the “Material Girl” video and married him on her birthday in 1985. The two co-starred in the 1986 box-office bomb Shanghai Surprise, produced by George Harrison. She filed for divorce from Penn in 1989, citing irreconcilable differences.
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1986
Image Credit: Courtesy Photo Madonna’s third album, True Blue, was dedicated to her then-husband Sean Penn (“true blue” was her nickname for him). The 1986 album saw Madonna debut a more adult look, tackle more mature themes (including teen pregnancy) and gave her three No. 1s on the Hot 100: “Live to Tell,” “Papa Don’t Preach” and “Open Your Heart.”
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1987
Image Credit: Paul Natkin/Getty Images In July 1987, Madonna kicked off her first world tour, the Who’s That Girl World Tour. Named after a screwball comedy she starred in alongside Griffin Dunne (and the film’s No. 1 title track), the tour was a massive success, although Pope John Paul II urged people to boycott the show in Italy.
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1989
Image Credit: Courtesy Photo Madonna once again courted controversy in 1989 with the release of her “Like a Prayer” video, which featured her kissing a saint and dancing in front of burning crucifixes. As a result of the outrage, the Vatican condemned the video and Pepsi canceled a contract with Madonna. Both the single and album of the same name hit No. 1.
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1992
Image Credit: GI Madonna founded her entertainment company, Maverick, in 1992. Gus Oseary took over as CEO in 1998. After dueling lawsuits between Maverick and Warner Music Group in 2004, Maverick became a subsidiary of the latter.
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1990
Image Credit: Courtesy Photo Inspired by the New York underground ballroom scene (captured in the 1990 documentary Paris Is Burning) of the ’80s, Madonna took vogue-ing from the gay underground to mainstream America with her No. 1 hit and iconic video, which paid homage to classic Hollywood stars.
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1990
Image Credit: Everett Collection Madonna played femme fatale Breathless Mahone opposite Warren Beatty in the 1990 film Dick Tracy. Beatty and Madonna began a brief relationship during filming.
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1990
Image Credit: Courtesy Photo One of two new songs included on her compilation The Immaculate Collection, “Justify My Love” featured Lenny Kravtiz and a Public Enemy sample. The 1990 video — highlighting S&M and bisexuality — was banned by MTV. The VHS release of “Justify My Love” became a bestseller.
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1991
Image Credit: Mary Evans/Ronald Grant/Everett Collection The Madonna-approved 1991 documentary Truth or Dare followed her Blond Ambition World tour, including the Toronto show where police reportedly threatened to arrest her if she simulated masturbation on stage. Madonna did just that, but no arrests were made.
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1992
Image Credit: Columbia Pictures/courtesy Everett Collection Madonna played the cigarette-smoking, wise-cracking ball player “All the Way” Mae alongside pal Rosie O’Donnell in 1992’s A League of Their Own. “This Used to Be My Playground,” a ballad she sang over the end credits, reached No. 1 on the Hot 100.
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1992
Image Credit: Courtesy Photo Madonna released the coffee-table book Sex in 1992 alongside her Erotica album. The book featured erotic and nude photos, including shots that simulated S&M and analingus. Vanilla Ice, Big Daddy Kane, Naomi Campbell and Isabella Rossellini all appeared in the book. This marked the peak of Madonna’s transgressive period. While negatively received at the time, some now consider it a key piece of post-feminist art.
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1994
Image Credit: Courtesy Photo On March 31, 1994, Madonna appeared on Late Show With David Letterman. She said “fuck” 14 times, asked him to smell her underwear (after handing them to him) and told him, “Money’s made you soft.” It was the most-censored network talk-show appearance in history.
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1994
Image Credit: Courtesy Photo Released in 1994, Madonna’s Bedtime Stories single “Take a Bow’ hit No. 1 in 1995 and became her longest-running Hot 100 chart-topper, staying there for seven weeks.
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1996
Image Credit: Buena Vista Pictures/Courtesy Everett Collection After fighting hard to play real-life Argentinian First Lady Eva Peron in the theatrical adaptation of Broadway’s Evita, Madonna won the part in the 1996 film and a Golden Globe for her performance.
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1998
Image Credit: Courtesy Photo After becoming a mother and taking on her most serious dramatic role in Evita, Ray of Light signaled a similar maturation for Madonna, both musically and thematically. Several songs on the 1998 album nodded to her growing interest in Kabbalah.
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2000
Image Credit: Courtesy Photo Continuing in the techno direction of Ray of Light, Madonna released Music in 2000. The album was her first No. 1 on the Billboard 200 since 1989 and the title track was her first No. 1 on the Hot 100 since “Take a Bow.”
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2003
Image Credit: Chris Polk/FilmMagic Nearly 20 years after her breakthrough performance at the first VMAs, Madonna performed alongside Britney Spears, Christina Aguilera and Missy Elliott at the 2003 VMAs. Her onstage kiss with Britney and Christina remains one of the most talked-about moments in VMA history. Madonna duetted with Spears on “Me Against the Music” that same year.
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2007
Image Credit: Dave Hogan/Getty Images In 2007, Madonna left Warner Bros., starting a 10-year, $120 million deal with Live Nation.
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2008
Image Credit: Franziska Krug/Getty Images Madonna made her directorial debut in 2008 with Filth & Wisdom, a London-set comedy that received mixed reviews. Her next film, the historical drama W.E., received much better notices. Also in 2008, Madonna was inducted into the Rock and Roll Hall of Fame.
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2012
Image Credit: Kevin Mazur/WireImage In 2012, Madonna performed the most-watched Super Bowl halftime show up until that point. She was joined by Nicki Minaj, Cee Lo Green, LMFAO and M.I.A., who controversially flipped her middle finger during the performance.
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2014
Image Credit: Kevork Djansezian/Getty Images Madonna performed “Open Your Heart” at the 56th Grammys in 2014 while Queen Latifah officiated the weddings of dozens of gay and straight couples on live TV.
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2015
Image Credit: Courtesy Photo In 2015, Madonna embraced new media (Snapchat, Grindr) while promoting her 13th studio album, Rebel Heart. She also announced a massive worldwide tour in support of the effort, which will kick off Aug. 29 in Miami.