18. Denis Leary
With a line-up primarily made up of straight, white guys, the Leary roast hearkens back to the boys' club feeling of the Friars' events — minus the elderly Jews. While friends and Rescue Me costars like Adam Ferrara and Lenny Clarke take pot shots, Leary perches on a barstool next to Kiefer Sutherland and Liz Hurley because, uh, he knows people. When highlights include a swearing priest, Christopher Walken's taped appearance and a ridiculous bit about Leary's joke-slinging Irish wolfhound, it's easy to wish that a seasoned MVP like the late Greg Giraldo hadn't riled Leary during their Tough Crowd With Colin Quinn appearance (the two almost came to blows) ; this one desperately needed a ringer.