If you want to see Jon Stewart cry a little on the inside, ask him about his sadly brief career as an actor.
See which comedians made the cut after the jump.
Rundown: Adam Sandler may just be the most successful stand-up comic ever to transition to film. Using "Saturday Night Live" as his bridge, Sandler successfully did what his contemporaries (like Janeane Garofalo, the sweetly self-deprecating comic turned Fox News punching bag) couldn't: He maintained an acting career that lasted beyond the '90s, continuing to thrive in starring roles well past the peak of his SNL days. In films as diverse as Punch-Drunk Love, Reign Over Me, and yes, Happy Gilmore, Sandler has reinvented himself more times than John Travolta.
Memorable Quote: "The price is wrong, bitch."
Richard Pryor in The Toy
Rundown: The late Richard Pryor, the comedian whom Jerry Seinfeld once called "The Picasso of our profession," brought his brand of tell-it-like it is, social-commentary comedy to his role as a man selected to be the toy of a spoiled little boy. Like Pryor himself, the strange and whimsical film packs a punch as he teaches both the little boy and his father how to be better human beings.
Memorable Line: "We are gonna say, 'Hey God! life's unfair!' You know what he's gonna say? 'Tough Titties!'"
Russell Brand in Forgetting Sarah Marshall
Rundown: As sexually-sexual rocker Aldous Snow in Forgetting Sarah Marshall, Brand delivered a performance that more than lived up to Jason Segel's witty writing. Brand slinks across the screen imparting pearls of wisdom, like a very well-dressed and casual Christ. Overnight, the British stand-up comic became an international superstar, and America welcomed him with open arms.
Dane Cook in My Best Friend's Girl
Memorable Line: "Yet, I am concerned that you've had a few too many drinks and now your fingers are in this bowl like it's one of your sorority sisters."
Daniel Tosh in The Love GuruRundown: When I spoke with Daniel Tosh in 2008, Mike Myers' not-so-favorite mistake The Love Guru was out on DVD and universally acknowledged as one of the worst films ever. "I think it's good that I've never seen it, because that way when people make fun of me I'm like, 'I assume it was really good!' said Tosh. As the random angry man in a cowboy hat who starts a bar fight, Tosh is a rare gem in the movie for the self-awareness with which he delivers his awful, awful performance.
Memorable Line: "Looks like I'm gonna have to shove these love beads someplace special."