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Britney Spears’ 11 Best Award Show Moments

From wearing a live python to that Madonna kiss, a look back at live awards show performances that made her a star

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Britney Spears, Madonna and Christina Aguilera perform opening act at the 2003 MTV Video Music Awards.

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On Sunday, the Billboard Music Awards will open with a performance by pop superstar Britney Spears, who'll run through a medley of her hits and accept the Millennium Award for "outstanding career achievements and influence in the music industry." Among those achievements: A slew of appearances both performing and presenting at awards shows, which have been so impressed by her dominance that they've invented new trophies just for her. Here are a few of her biggest moments from ceremonies past.

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Britney Spears at the 1999 Teen Choice Awards in Los Angeles.

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Teen Choice Awards, 1999

Britney's first awards-show performance began on a show that she introduced alongside fellow Mousketeer-turned-legit-pop-star Christina Aguilera. Her breakthrough hit "…Baby One More Time" picked up the Choice Music: Single award, and the versatile all-white outfit she wore during her medley of the ballad "Sometimes" and the feisty "(You Drive Me) Crazy" helped her show off her serious side and her slick moves.

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Britney Spears performs during the 1999 MTV Music Video Awards in New York City on September 9, 1999.

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Video Music Awards, 1999

Britney and the Video Music Awards would go on to have a storied history together, and for her first appearance on MTV's annual bacchanal, she ran through a technofied remix of "…Baby One More Time" before ceding the cafetorium floor to 'N Sync. (She didn't pick up any Moonmen, but those would come raining down on her later.)

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Britney Spears performs on stage at the 42nd Annual Grammy Awards in Los Angeles, California on February 23rd, 2000.

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Grammy Awards, 2000

Music's most serious ceremony got its first taste of Britney as Artist with her heartfelt version of "From the Bottom of My Broken Heart," which opened with a sequence depicting Young Britney as an aspiring pop star and led into Britney playing balladeer while clad in a cloud of tulle. That, however, quickly led to an army of robots taking over the stage, and Britney ditched the fairy-princess garb for a bodysuit that made dancing to "…Baby One More Time" (not to mention a brief interlude where Britney's footwork took center stage) much easier. Britney was shut out of the Grammys that year (she lost Best New Artist to Christina Aguilera), but her time would come in 2005, when "Toxic" took home the Best Dance Recording trophy.

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American pop singer Britney Spears performs onstage at the 2000 MTV Video Music Awards held at Radio City Music Hall in New York City on September 7, 2000. (Photo by Scott Gries/Getty Images)

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Video Music Awards, 2000

Britney's symbiotic relationship with the VMAs continued in her second year on the broadcast, when she performed the Rolling Stones' "(I Can't Get No) Satisfaction" while clad in a suit; that garment was quickly disposed of in favor of a nude, glitter-covered bodysuit, which she wore while performing the similarly sultry "Oops!… I Did It Again." (That bodysuit, or an homage to it, would show up again in the spy-catching clip for "Toxic.") The video was up for three Moonmen that year, but lost.

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Britney Spears & Justin Timberlake of NSYNC (Photo by Jeffrey Mayer/WireImage)

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American Music Awards, 2001

Britney performed her against-all-odds hit "Stronger" at Dick Clark's annual celebration of America's favorite musicians, which had awarded her with the Favorite New Pop/Rock Artist trophy the year prior. But this appearance of Britney's is probably more notable for her red-carpet wear — she and then-beau Justin Timberlake showed up in their own brand of formalwear, namely matching light-dyed denim outfits. (It was a more innocent time.)

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Britney Spears performs (Photo by KMazur/WireImage)

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Video Music Awards, 2001

The Neptunes collaboration "I'm A Slave 4 U" was a sign that Britney was growing up, and her live debut of the song on the 2001 Video Music Awards (at the Metropolitan Opera House, for added grown-up effect) proved that she wasn't messing around — she carried a live Burmese python while dancing around the stage, as a white tiger prowled nearby. The song's spaced-out beat was neatly matched by the nervous energy that can only be achieved by the possibility of a star being devoured by something non-human on TV.

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Michael Jackson speaks after Britney Spears presented Michael with a birthday cake at the 2002 MTV Video Music Awards at the Radio City Music Hall in New York City, New York (Photo by Kevin Mazur/WireImage)

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Video Music Awards, 2002

"I'm a Slave 4 U" was up for three Moonmen in 2002, and Britney was brought out to give King of Pop Michael Jackson a special trophy in honor of his 44th birthday. "I consider him the artist of the millennium," Britney said while introducing Jackson, who took this to believe that the award he was being given was actually an Artist of the Millennium Award. He'd already had one Moonman — the Michael Jackson Video Vanguard Award, which was rechristened in 1991—named after him, so why not go all the way?

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Video Music Awards, 2003

As a member of Madonna's wedding party during the show-opening medley of "Like a Virgin" and "Hollywood," Britney was allowed to kiss the bride — and kiss she did, in a Sapphic smooch that was felt around the world and that finally, once and for all, shed her teen-pop image for good. "She's been looking for her Olivia Newton-John in Grease moment for the last couple of years," industry observer Sean Ross told the New York Daily News. "Toxic," which came out a few years later, would cement the shift in her rep.

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LOS ANGELES, CA - SEPTEMBER 07: Singer Britney Spears on stage at the 2008 MTV Video Music Awards at Paramount Pictures Studios on September 7, 2008 in Los Angeles, California. (Photo by Chris Polk/FilmMagic)

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Video Music Awards, 2008

After a shaky show-opening performance at the similarly shambolic 2007 Video Music Awards in Las Vegas, Britney was ready for redemption, and the 2008 VMAs, held in Los Angeles, provided plenty. Britney opened the show with an introduction and subsequently swept all her categories, including Video of the Year, for the self-referential "Piece Of Me"; even with her many VMAs appearances, the trophies were her first. She ended the show by being whisked away by host Russell Brand into the wilds of Paramount Pictures Studios on a golf cart. A happy ending – even if she didn't perform.

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OFFENBURG, GERMANY - NOVEMBER 27: Britney Spears performs at the Bambi Awards 2008 Show on November 27, 2008 in Offenburg, Germany. (Photo by Sascha Baumann/WireImage)

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Bambi Awards, 2008

Britney continued her comeback tour with a rollicking performance of "Womanizer" at this German awards ceremony, where she showed off the ringleader getup that she'd wear during the campaign for her comeback album Circus and took home the Best International Pop Star trophy.

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LOS ANGELES, CA - AUGUST 28: Lady Gaga and Britney Spears speak on stage at the The 28th Annual MTV Video Music Awards at Nokia Theatre L.A. LIVE on August 28, 2011 in Los Angeles, California. (Photo by Kevin Mazur/WireImage)

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2011 Video Music Awards

Lady Gaga's alter ego Jo Calderone, channeling both Gaga and Andrew Dice Clay, introduced Britney as a "pop music legend" who had irrevocably changed the music industry before the Michael Jackson Video Vanguard Award tribute during which a phalanx of dancers recreated some of Britney's biggest MTV hits. While Gaga-slash-Jo got rebuffed when she tried to recreate the starlet-on-starlet buss that got tongues wagging in 2003, Britney was still gracious, thanking the audience for what would be her fifth Moonman.

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