1999 – “Baby… One More Time”
Thoughts: My, how Brit-Brit grew up fast! She busted out her debut single “Baby… One More Time” for her premiere performance at the VMAs, and yet the difference between Spears-the-schoolgirl in the song’s video and the full-formed teen goddess we see here is staggering. However, the remix of the song itself is unappealing, and Brit announcing “I’d like to introduce a few friends of mine” a full minute before *NSync’s entrance makes this whole number sort of awkward. Still, Brit looks and dances fantastic.
2000 – “Satisfaction” / “Oops… I Did It Again”
Thoughts: Brit’s glittery tux stripped aside to reveal a nude bikini-top costume are the things classic clips are made of. As for the rest of the performance, we dare you to look away from the magnetic pop star as she bursts through every move with unbridled power and authority. And she’s only 18-years-old here! Plus, that feisty, sly look she gives at the end? We’re in love all over again.
2001 – “I’m A Slave 4 U”
Thoughts: The image of Britney in one of her sexiest outfits of all time slithering toward the camera with a snake around her shoulders became instantly iconic the moment it happened. Between this steamy performance and the previous year’s “Oops” number, Britney cements her title as the VMA’s unofficial mascot.
2003 – “Like A Virgin” / “Hollywood”
Thoughts: Pairing Britney with her supposed rival Christina Aguilera and well-known mentor Madonna sounds like pure perfection in theory, but the whole performance reeked of desperation. The kiss between Brit and Madge was all anyone talked about the next day, with the unexciting rendition of Madonna’s “Like A Virgin” and American Life single “Hollywood” — not to mention Madge’s smooch with Xtina and Missy’s entire appearance — quickly forgotten. All involved artists are a lot better than this. (Cutting to the look on Brit’s then-recent-ex Justin Timberlake after the kiss almost seemed like the entire reason for this stunt to take place.)
2007 – “Gimme More”
Thoughts: Britney’s return to the VMA stage — her first performance in four years — was THE reason to watch the awards show that year. She had been going through several months of extremely public struggles, and everyone wanted to see what the performance would be like. Would it be a return to form? Would she even show up? Turns out, yes, she did show up, but she probably shouldn’t of. The number was a complete mess, Brit was no longer the impeccable specimen of physical perfection (moreso for her hair than her body), and she looked either on the verge of tears or a nap the entire time. Like many of her previous trips to the VMAs, it became instantly iconic, but for the wrong reasons.