The teen queen made her MTV Video Music Awards debut in 1999. Decked out in a glistening purple crop top, matching pants and sneakers, Spears performed her smash hit first single “Baby One More Time.” Her sultry dance moves heated up the stage, which was set to look like a high school in a nod to the track’s now- iconic video. After her song, Brit Brit passed the baton to ‘NSYNC, who performed “Tearin’ Up My Heart.”
Spears’ second VMA performance – the show opener – made quite the sexy splash. She began with her Rolling Stones cover “Satisfaction,” modestly clad in a black-and-white tuxedo and hat. But soon, Spears was stripping down to a nude, shimmering two-piece that flaunted her world-dominating abs. Blonde locks flowing, the pop star topped off her set with the title track to her then-latest album, “Oops!… I Did It Again.”
Perhaps the most unforgettable of Spears’ many VMA performances, her 2001 gig included one shocking onstage guest. Spears began by emerging from a cage, which also contained a white tiger, belting “Slave 4 U” and busting some seriously steamy dance moves. Mid-song, a back up dancer helped Britney drape the ultimate accessory across her shoulders: a yellow python. The slithering dance partner earned a lasting place in Spears’ heart. “Sometimes I wonder what this snake is up to these days,” she tweeted in 2012. Later adding, “Snake update: I’ve hear she’s alive and doing well, and that her name is Banana! This makes me smile.”
The world was denied a Britney Spears VMA performance in 2002, but received a pretty satisfactory consolation prize: The star was tasked with introducing Michael Jackson for a special celebration of the king of pop’s birthday, which happened to be the same day as the ceremony. Spears wore a leather mini dress and hat for the occasion. The moment became infamously awkward when Spears described Jackson as “the artist of the millennium” in her introduction, prompting the “Beat It” singer to deliver an acceptance speech for an imaginary “artist of the millennium” award.
It was the year of the kiss heard ’round the world. Spears joined Christina Aguilera, Madonna and Missy Elliot in the VMA opener. Aguilera and Spears kicked off the performance with a “Like a Virgin” tribute to the OG pop star’s 1984 VMA appearance, each wearing ’80s-inspired wedding dresses. Madonna then appeared at the top of the stage’s giant cake where she began her song “Hollywood.” The three singers had the crowd going wild when they engaged in a racy triple kiss, quickly securing the performance a spot in VMA history.
It was supposed to be Spears’ triumphant comeback to the VMA stage after a challenging era in her personal and professional life, but her much-buzzed about performance of “Gimme More” was widely deemed lackluster. “She was extremely nervous. It’s been awhile since she’s done this, and she was performing in front of all her peers, on live TV. She just got out there and froze,” a source told PEOPLE about the mishap shortly after the show. “People who were at rehearsal saw something else. It was good. It really was.”
A year after her disappointing “Gimme More” showing, Spears triumphantly returned to the VMAs and took home the first-ever Moonman statues of her career. She nabbed the awards for best female video, best pop video and even the night’s biggest honor, video of the year, for “Piece of Me.”
Spears earned the award for best pop video for “Womanizer,” but was away on tour during the broadcast. She accepted the honor from afar alongside her backup dancers in a sweet video.
A team of dancers dressed in Britney Spears-inspired costumes paid tribute to the Michael Jackson Video Vanguard Award-winner’s career with an explosive routine. “One of my biggest inspirations was Britney Spears,” Lady Gaga said in her introduction. “Britney taught me how to be fearless – she taught us all how to be fearless. She’s a pop music legend and the industry would not be the same without her. Throughout the years, Britney has given us some of the most iconic music videos and stage shows of our time, and that’s why tonight MTV and myself are honoring Britney and her influence on music videos and dance.” When she ascended to the stage to accept the statue, Spears teased the crowd – and Gaga – by almost kissing the famous fan. Brit Brit also took home the best pop video award for “Till the World Ends.”
Returning to the VMAs stage for a hotly anticipated performance, Brit brought the sex appeal for a racy rendition of her new single “Make Me.” A barley there bodysuit, lots of dancing and even more hair flips took fans back to classic Britney.