9. Rob Reiner
In Reiner's roast, you can feel the smoke-filled, chummy back room of Friars Club slowing having its furniture rearranged by a network seeking viewership. Old-guard regulars like Freddy Roman and Abe Vigoda are there, but so are younger outsiders, like Kevin Pollak and walking punchline Vanilla Ice. Reiner is a wonderfully jovial target, egging on attackers who jab him about marriage to Penny Marshall, his weight, and then his weight again. Robert Smigel's appearance as Triumph the Insult Comic Dog is the best example of playing both sides against the middle, mocking the age of the club's members and its rituals while readily participating in them: "Have you ever seen Alan King naked in the steam room? Normally I have to eat grass if I want to puke."