Janet Jackson at Super Bowl XXXVIII
Air date: February 1, 2004
It's the Citizen Kane of televised nip-slips—so unexpected, and on such a large stage, that nothing else will ever come close. If Beyoncé were to whip out both breasts and put on a puppet show with them when she performs this year in New Orleans, it would rate as just the second most shocking Super Boob display. Janet's strangely ornamented right nipple is a living legend, and so is Justin Timberlake's terrified reaction.