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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.

Kevin Kane/WireImage/Getty

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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Kevin Kane/WireImage/Getty

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)

Sascha Baumann/WireImage/Getty

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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