#8: Janet Jackson And Justin Timberlake’s Nipplegate

You can bump ‘n grind while simulating orgasm on MTV, and you can cram prime-time TV with cleavage galore, but you can’t bust out the right half of an R&B diva’s very substantial rack during the world’s most-watched sporting event. Justin Timberlake probably had no idea what kind of maelstrom he’d set off when, during the halftime show of the 2004 Superbowl, he ripped open Janet Jackson‘s bustier and her luscious boob popped out, replete with a sunburst nipple shield, The stunt – famously deemed a “wardrobe malfunction” – sparked over half a million complaints to the FCC, and framed Jackson a pop pariah.

The so-called Nipplegate scandal happened at a time when Jackson could have benefited from a little notoriety. But the dreary Damita Jo, released a few weeks later, kinda stiffed, and Jackson never pulled out of her career slump – a bummer. But perhaps the real bummer is that even the slightest whiff of sex has been banished from Superbowl acts ever since.