19. Janet Jackson, Justin Timberlake, P. Diddy, Kid Rock, Jessica Simpson and Nelly (2004)
We've seen the nipple and the damage done. Without question the most famous halftime show ever, the one that forced a generation of Americans to hear their moms utter the word "aureole." It killed off Janet Jackson's previously unstoppable career – almost 20 years of hitmaking, zapped in one breast-bounce. It damn near killed Justin's too, as his clumsy (and none too gallant) handling of the controversy ended his post-N'Sync honeymoon with the public. (It took two years and Timbaland for JT to get his sexy back.)
The music was mostly great, but the fallout was poisonous. The Bush administration (especially Colin Powell's son at the FCC) led a hysterical crusade to demonize MTV and Miss Jackson. You could pinpoint this as the moment MTV decided to bail out of the music business entirely. All around, a disastrous moment for America. Also, Jessica Simpson sang.