50. Vanilla Ice

From wannabe gangster, to wannabe MMA fighter... Looking back, it seems that Vanilla Ice may have actually been the greatest, most elaborate ongoing prank in pop culture history. Seriously, a to-the-extreme rapper gets street cred when he's wearing star-spangled windbreakers and Hammer-esque pants? He was basically Robert Matthew Van Winkle's Borat, punk'ing America into wicked album sales and a Grammy nomination. Two decades later, though, it's still not clear who got the last laugh.