Super Bowl XXXVIII, 2004
Performers: Janet Jackson, P. Diddy, Nelly, Kid Rock, and Justin Timberlake
Finally, we arrive at what's arguably the most controversial moment in Super Bowl halftime history. While it was a hot topic at the time, anybody who still thinks that Justin Timberlake forcefully ripping off a piece of Janet Jackson's top to reveal a perfectly placed nipple adornment was anything but intentional is giving way too much credit to these stars. Justin Timberlake croons, "I'm going to have you naked by the end of this song," and with not an ounce of surprise on either performer's face, or effort to cover it up, does just that (well, for one boob at least). Whether Janet was the mastermind or simply the recipient, we'll never know (except we know she was totally in on it), but what better way to keep your name relevant to the modern pop scene than by cementing your nipple in the annals of history? One breast to rule them all. And one moment to crown 2004 as the most ridiculous half time show in Super Bowl history.