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.
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.
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.)
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.
Music Awards, 2000
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.
