Criteria for being on this list; at least one classic stand up, and a successful career of any kind (be it stand up, movies, etc.)
5. Dave Chappelle – Still a relatively young comedian and actor, Chappelle had an insanely funny stand up, Killin’ Them Softly (2000), and a very successful TV show. Though he went legally insane for a while and moved to Africa (some say to kick some kind of addiction), he’s got a great mind for comedy.
Dave got his big break in Half Baked (which he also wrote), but sadly hasn’t done a single movie with a great deal of success since then. He does, however, have an “in-development” deal, which means it will be a couple years until we see something new from Dave, be it movie or TV series.
Killin’ Them Softly is wall-to-wall laughter, with subject matter that includes coming to grips with being famous, Bill Clinton’s blowjob scandal, the corruption of police and the government, and how bad ghettos have gotten. His wildly successful TV series had a great mix of music, stand up, and comedy bits (the most famous being the Rick James segments), not to mention the support of a very important demographic, high school and college students.
Chappelle has one other stand up, which I haven’t seen, For What It’s Worth (2004).
4. David Spade – One of the funniest stand up specials of all time, Take the Hit (1998). Although Take the Hit is the only stand up that’s been released by Spade, coupled with his very successful Hollywood career, it’s enough to land Spade a spot in my top 5.
This former SNL star has been on 2 great TV shows (excluding SNL), The Showbiz Show and Just Shoot Me. At first, I thought that he was nothing more than a Chris Farley sidekick, but shortly before Farley's death Spade decided to spread his wings, and eventually landed a spot on Just Shoot Me (playing the effeminate yet mouthy secretary for a popular fashion magazine). Spade has starred in some very funny movies such as Dickie Roberts, Black Sheep, Tommy Boy, PCU, and (written and starred in) Joe Dirt.
Take the Hit is a bit more topical than other stand ups, but I would say it still stands the test of time. JonBenet Ramsey, episiotomy operations, growing up in Arizona, teenage dating, and “…things that never happened, people I’ve never met” are some of the great Spade bits of this classic stand up. Plus, he has dated (is dating?) Heather Locklear.
3. Richard Pryor – This isn’t just the man that paved the way for “dirty” comics, he revolutionized stand up comedy. His stand up was the beginning of political in-correctness. He was able to inject humor into normally unfunny and racially tense situations, pointing out the absurdity of racism. The only super funny Pryor material I remember (from the 2 stand ups I’ve seen) would be the difference between a black guy and a white guy getting away from a snake.
Pryor had his own TV show for a short while, and did a few bad movies. His downfall was trying to get away from his roots of cursing and controversial material. Superman 3, The Muppet Movie, and Car Wash are a few of his more famous movies (and apparently, he was involved in writing Blazing Saddles). His more well known stand ups are Live in Concert (1979) and Live and Smokin’ (1971). Richard Pryor died in December 2005 of a heart attack in Los Angeles.
Coming Soon...the top 2 stand up comics, and runners up!