Best: Aerosmith, Britney Spears, ‘N Sync, Nelly, & Mary J. Blige, 2001
There were a couple of things that made the 2001 Super Bowl performance so weird. First of all, it featured two performers at the peak of their careers: Britney Spears and Justin Timberlake of ‘N Sync. When Rolling Stone talked about the performance of “Walk This Way,” it said it “has to be one of the most demented three-minute spectacles ever aired on TV. Britney, in silver football pants, starring as the Missy Who Was Ready to Play. Mary J. Blige wailing along. Nelly rapping over Joe Perry’s guitar solo. Really, the whole gloriously sleazy history of American pop music is here in this performance.”