#5. Janet Jackson's Nipplegate
Time Stamp: 2/1/2004
A former Mouseketeer and white male pop heartthrob, exposed the pierced nipple of Jackson, a black female music icon, during the Super Bowl, which is the biggest TV event of the year. The phrase “wardrobe malfunction” became a thing, and the half-second exposed boob became a launch pad for discussions on indecency, race and sex, and countless jokes. Biggest loser of the night was Viacom as MTV lost Super Bowl halftime production duties and CBS got hit with the biggest FCC fine in history.