2. Hugh Hefner
Sure, going after Hef feels like shooting fish in a barrel. But in the world of roasts, easy targets can inspire comedians to transform overworked premises into barbs with perfect accuracy. Take this summation from roastmaster Jimmy Kimmel: "What can you say about Hef that hasn't already been said by 1,000 young women with his cock in their mouths?" There's also a kind of easter egg in this roast, material that was cut from the final broadcast but was highlighted by 2005 documentary The Aristocrats, that pushes it to legendary status. The roast itself was filmed in late September 2001, and Gilbert Gottfried made jokes about the World Trade Center attacks that were too close to home. Rather than give up, Gottfried redoubled his efforts in telling the well-known dirty joke known as "The Aristocrats," and won only the audience's love with a wild torrent of filth. In one fell swoop, the diminutive comic led the room through some of the most cathartic, you-have-permission-to-laugh-again howling you've ever heard. It's one for the ages.