Here's three with two clips each; hopefully somebody steps up with a third clip for each of them!
DANIEL TOSH
Competely Serious -
The one-minute salvia/cinnamon/cracker/coconut-challenge (Tosh.0) - http://www.funnyordie.com/videos/eb187fc116/tosh-0-extreme-salvia-challenge
DOUG STANHOPE
Bobby Barnett -
Transvestite-Hooker Incident -
DAVE ATTELL
1995 Young Comedians Festival -
Jagermeister advertising (Captain Miserable) -
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http://img812.imageshack.us/img812/3492/eponaharr.jpg
Nominate SuperNiceDog's Guru-choice, then Epona.