15. Drew Carey
One of the few Friars Club productions to be broadcast on Comedy Central, this special features a number of older, revered comedians whom very few young viewers would know on sight: Kip Addota, Dick Capri, Alan King. It's also got a hammy, old-fashioned borscht-belt sensibility, and not even younger all-stars like Margaret Cho can't stave off a certain sense of mustiness. Thankfully, Dave Attell livens things up by working blue when talking about "Mr. Las Vegas TV Show" ("We all know what your favorite song is, and that's your balls slapping against a hooker's ass — it's got a great beat and it always makes you hungry"), and Jeff Ross makes his first roast appearance here, dropping zingers like, "Drew Carey is to comedy as Mariah Carey is to...comedy."