I believe Richard Pryor to be the best stand-up comic of all-time (closely followed in the social-critic realm by Bill Hicks and George Carlin), but Dave Chappelle is promising to be a worthy successor. This HBO special from 2000 has achieved something of a cult status on peer-to-peer networks since its airing, especially in audio form, and as such has gained even more popularity since Chappelle's venture into Comedy Central's "Chappelle's Show" (which is finishing its third and apparently final season right now).
Looking back, I find this to be even funnier than his comedy show. Whereas his (hilarious) sketch show can become a bit repetitive at times and is almost always dealing with racial stereotypes and such, "Killin' Them Softly" touches on everything - beginning with blacks and whites ("DC has changed!"), moving on to crime, then television shows, and of course marijuana.
My personal favorite bit has got to be Chappelle's observations on children's entertainment. He remarks how Pepé Le Pew is practically a rapist and encourages children to "take the pussy(cat)" and how racist "Sesame Street" was. ("Yeah, Oscar! You're a grouch." - "I live in a trash can! What do you expect!") Don't forget The Count: "I know a pimp when I see one!" To be honest I've found Chappelle's television show to become a bit stale sometimes (even though I'm a huge fan of it) but I was blown away - his stand-up comedy is even better. It's rare that I find myself laughing out loud at comedy acts, but even without watching him on stage, his vocal performance is gut-busting. The 911 phone call bit is classic.
I don't want to discredit Richard Pryor and say this is funnier, but if you listen to some of Pryor's older stuff, Chappelle is touching on the same issues as he did in the 1960s and '70s and is, at times, actually doing it even funnier. Of course, Chappelle has some way to go before matching Pryor's iconic status or even his later fusion of outrageous comedy and social satire in the mid-'70s through the early '80s (which surpasses the stuff here), but those comparing him to Pryor have a reason to do so.
