Britney Spears cemented herself as a pop culture icon with the release of her suggestive first single, “…Baby One More Time” and its tantalizing music video in 1998. Throughout her chart-topping career, the entertainer has gone through her fair share of highs and lows. From her electrifying performances to her heartbreaking breakdown in 2007, the superstar has kept Us watching her every move for nearly two decades. Click through to see the undisputed Princess of Pop’s most iconic moments.
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Britney Spears cemented herself as a pop culture icon with the release of her suggestive first single, “…Baby One More Time” and its tantalizing music video in 1998. Throughout her chart-topping career, the entertainer has gone through her fair share of highs and lows. From her electrifying performances to her heartbreaking breakdown in 2007, the superstar has kept Us watching her every move for nearly two decades. Click through to see the undisputed Princess of Pop’s most iconic moments.
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The singer burst onto the music scene with the 1998 release of her now-legendary first single, "...Baby One More Time" and its accompanying music video, for which the then-16-year-old donned a provocative schoolgirl ensemble. She immediately became an idol to young female fans and an object of affection for legions of teenage boys.
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Britney shot her first Rolling Stone cover in 1999, the same year her debut album, ...Baby One More Time, shot straight to No. 1. The pop star, then just 17, slipped into a number of skin-baring ensembles — including lingerie — for the David LaChapelle shoot, which sparked outrage among her tween fans' parents. In 2008, the singer's mother, Lynne, explained how her daughter ended up posing for such controversial photos. “We were in shock at what was going on, and we were in awe. We didn’t have any choice in the pictures," she said during a Today show appearance. "We had no one that could tell us what we were supposed to be doing.”
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Britney attended the Grammy Awards for the first time in 2000 when her track "...Baby One More Time" was nominated for Best Female Pop Vocal Performance and the pop ingenue, herself, was nominated for Best New Artist. While she went home empty-handed (and lost the Best New Artist award to then-rival Christina Aguilera), the young star still made a splash at the ceremony by stunning on the red carpet in a Marilyn Monroe–inspired gown and slaying on stage with an epic live performance.
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Britney dropped her record-breaking sophomore LP, Oops!...I Did It Again, in 2000. She flaunted both her talent and her insanely fit physique for an energetic performance of her second album's titular single at the 2000 MTV Video Music Awards, in which she stripped down to a sparkly nude bra top and sheer pants.
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Britney's next career milestone came in January 2001, when she performed at the Super Bowl XXXV halftime show. The "Stronger" songstress took the stage with Aerosmith and boy band du jour 'N Sync, the group that her then-boyfriend Justin Timberlake fronted at the time. Dressed in a football-inspired crop top and low-rise pants, Brit joined Steven Tyler and his iconic rock band for a hard-hitting rendition of the 1975 anthem “Walk This Way.”
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Britney and Justin Timberlake, one of the most cherished celebrity romances of the early aughts, took couple dressing to the next level at the 2001 American Music Awards when they wore coordinating head-to-toe denim ensembles. In 2002, the former All New Mickey Mouse Club costars — who secretly began dating in 1999 — called it quits amid reports that Brit cheated on JT with choreographer Wade Robson.
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She lit up the stage at the VMAs yet again in 2001, when she performed her sexy song "I'm a Slave 4 U," the lead single from her eponymous third album. While it seemed uncertain whether Britney could live up to her titillating performance at the same awards show the year before, the singer amped up the shock value by writhing with an albino python in the middle of her dance-heavy set.
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Britney played the nerdy-yet-beautiful Lucy in the 2002 feature film Crossroads. While her acting in the Shonda Rhimes–penned teen drama was widely panned by critics, the Britney Army still has a soft spot for the movie, which also starred Zoe Saldana, Orange Is the New Black's Taryn Manning and former heartthrob Anson Mount.
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Yet another standout moment from the MTV VMAs. Britney opened the 2003 show with Madonna for a medley of the pop queen's hits including "Like a Virgin" and "Hollywood." Brit kissed the Material Girl (whom she calls her idol) midperformance and caused a media firestorm. The "Overprotected" singer's musical peer Xtina also participated in the number and gave Her Madgesty a peck, but failed to make headlines quite the way Miss Spears did.
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Britney was honored with her own star on the Hollywood Walk of Fame on November 17, 2003, shortly after she released her fourth studio album, In the Zone, which spawned hits such as "Me Against the Music," featuring Madonna, and her Grammy award–winning single "Toxic."
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Britney released the epic video for her No. 1 hit "Toxic" in 2004. Directed by Joseph Kahn, it featured the chart-topper dressed as several variants of herself: a sexy flight attendant, a raven-haired temptress, a redheaded dominatrix and, most iconic of all, an angelic blonde doused in nothing but diamonds.
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After filming several Pepsi commercials and serving as the face for the cola brand in 2001 and 2002, Britney appeared in a 2004 ad, which featured fellow hitmakers Pink and Beyoncé. The trio — standing in the middle of Rome's Colosseum and dressed in gladiator gear — sang a sexy cover of Queen's 1977 hit "We Will Rock You" and kicked back a few cans of the sparkling soda. The spot also starred Latin heartthrob Enrique Iglesias as a Caesar-inspired emperor.
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On New Year's Eve 2004, the "Everytime" singer married her childhood friend Jason Alexander in a quickie Las Vegas wedding ceremony. The marriage, Britney's first, created an uproar in the media and within the superstar's inner circle. Fifty-five hours later, their union was annulled. Alexander, who admitted to ABC News in 2012 that he and Brit were "doing drugs" before they tied the knot, claimed their short-lived romance was the real deal. "I went with my feelings," he said. "I was in love with her. ... I feel like she felt the same way."
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Britney met her future husband, Kevin Federline, during a night out in Hollywood in April 2004. Just a few weeks later, she invited the backup dancer and aspiring rapper on the European leg of her Onyx Hotel Tour. Not long after, the two became engaged and wed in a private Studio City, California, wedding ceremony September 18, 2004. They documented their love story via camcorder and their personal footage was packaged into a reality show called Britney & Kevin: Chaotic, which premiered on UPN in 2005. That same year, the couple welcomed their first child, Sean Preston. In 2006, Britney gave birth to her second son with K-Fed, Jayden James. Two months later, in November 2006, the pop star filed for divorce.
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During her second pregnancy, a black-haired Britney posed nude for the cover of Harper's Bazaar's August 2006 issue. "I think being pregnant is such an empowering feeling," she told the fashion magazine at the time. "And for mothers out there in general, you don't feel the most beautiful all the time."
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Britney's breakdown — reportedly fueled by substance abuse and an undisclosed mental illness amid a painful split and custody battle over her sons with now-ex-husband Kevin Federline — became strikingly apparent on February 16, 2007, when she made an after-hours trip to Esther's hair salon in Tarzana, California. She asked the shop's owner, Esther Tognozzi, to shave her head, but the beautician refused. So the troubled singer took the clippers herself and buzzed off her long tresses. Once she was finished, Tognozzi told the L.A. Times that the former child star looked in the mirror, with tears in her eyes, and said, "Oh, my God, my mom is going to be so upset at me."
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Shortly before checking into and out of rehab, a bald-headed Britney attacked a paparazzo's car with an umbrella following a visit to her estranged husband Kevin Federline's home in February 2007. Months later, she provided a bizarre explanation for her behavior. "I apologize to the pap for a stunt that was done 4 months ago regarding an umbrella," the "My Prerogative" songstress wrote on her website. "I was preparing my character for a role in a movie where the husband never plays his part so they switch places accidentally. I take all my roles very seriously and got a little carried away. Unfortunately I didn't get the part."
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In September 2007, Britney fans had hoped that her long-anticipated return to the VMAs stage would be the catalyst for a comeback. However, when the singer opened the award show in Las Vegas with a lackluster performance of "Gimme More," the lead single from her fifth studio album, Blackout, it was apparent that Britney had a long way to go before reclaiming her throne in the world of pop music.
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On January 3, 2008, Britney reportedly refused to turn over her two children to their father and her ex-husband, Kevin Federline. While the agitated singer's then-court-appointed monitor had put her eldest child, Sean Preston, in Federline's bodyguards' car, Britney locked herself in her bathroom with her younger son, Jayden James, who was 15 months old at the time. After authorities retrieved Jayden from Britney's bathroom, the mom of two was hospitalized on a 51/50 psychiatric hold, which set the stage for her road to recovery.
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Britney made a triumphant return to the VMAs in September 2008 when she took home three Moonmen for her "Piece of Me" music video, an autobiographical visual that illustrated the complicated relationship she'd had with the paparazzi in recent years. It won the awards for Best Female Video, Best Pop Video and Video of the Year.
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Less than a year after her psychiatric hospitalization, Britney bounced back better than ever. With the help of her family (especially her father, Jamie, who became her court-appointed conservator following her public breakdown), the pop star reclaimed her career with the release of her sixth album, Circus, which she dropped on her 27th birthday, December 2, 2008. She marked the occasion with an energetic performance of her hits "Womanizer" and "Circus" (which her sons were present for) on Good Morning America. Afterward, GMA's Diane Sawyer presented the singer with an elaborate birthday cake.
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After the release of Circus, Britney dropped her highly successful seventh studio album, Femme Fatale, released in 2011, which featured the chart-topping singles "Hold It Against Me," "Till the World Ends" and "I Wanna Go." After that, she took a brief break from recording and touring to become a judge on season 2 of Fox's The X Factor, alongside Demi Lovato, music exec L.A. Reid and the show's creator, Simon Cowell. Her 2012 stint on the singing competition lasted only one season. "I had an incredible time doing the show, and I love the other judges,” the blonde beauty said of her departure. “But it's time for me to get back in the studio."
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Following the December 2013 release of her eighth album, Britney Jean, the pop diva began her Las Vegas residency, Piece of Me, at the Axis at Planet Hollywood. The concert — which includes the "Work Bitch" singer's greatest hits — has been touted as the "best show in Las Vegas." Piece of Me remains a staple on the Sin City strip and has been extended into 2017.
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At the 2016 Billboard Music Awards, Britney — who performed an epic medley of some of her biggest hits, as well as a few deep cuts from her 2003 album In the Zone — was also honored with a Millennium Award. The coveted award has previously been given to artists such as Beyoncé and the late Whitney Houston.
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