- Dave Chappelle: [playing bongos in front of a crowd] 5,000 black people chillin' in the rain. 19 white people peppered in the crowd. Trying to find a Mexican.
- Dave Chappelle: Did you hear the one about the industrious prostitute?
- Mos Def: No, Dave.
- Dave Chappelle: She had a vagina implanted on her hip.
- Mos Def: Why, Dave?
- Dave Chappelle: So she could make some money on the side!
- Dave Chappelle: BAM!
- Dave Chappelle: [in a freestyle emceeing battle with a random fan] Your shirt says Free Tibet... ain't no niggas in Tibet!
- Dave Chappelle: That was "'Round Midnight" I was playing. That's the Thelonious Monk song. One of my favorite musicians, 'cause his timing was so ill. Every comedian is a stickler for timing, and Thelonious Monk was off time, yet perfectly on time. You should study it. If you're an aspiring comedian, or an aspiring musician, you should study it. Which brings me to my next point. Comedians and musicians were like this:
- [interlocks fingers]
- Dave Chappelle: . Every comic wants to be a musician. Every musician thinks they're funny. It's a very strange relationship that we have. Some musicians are funny. Some comedians can play. I'll give you an example: Mos Def - funny guy; Jamie Foxx - good singer and piano player. So you never know, you never know what kind of talent a person has. I ain't mediocre at both, but I've managed to talk my way into a fortune. Life, is a funny and unpredictable thing!
- Dave Chappelle: [regarding music and comedy] I'm mediocre at both and yet have managed to talk my way into a fortune.
- Dave Chappelle: Attention, Huxtables, there is a block party down the street. Bring Yourselves. BRING YOURSELVES! And bring Rudy, Theo, and Denise.
- Dave Chappelle: [singing a blues song] I woke up this morning, 'bout quarter to four. Went back to sleep, and I woke up... at... eight.
- [crew laughs]
- Dave Chappelle: Went back to sleep again and woke up at two 'cause I'm a comedian and I ain't got shit to do. Oh, yeah, baby, I got them comedy blues. I just hang out all day, baby, cause I ain't got shit to do with you.
- Dave Chappelle: [Talking] Right, now, now. What kind of blue musician would I be if I didn't talk shit over the music?
- [crew laughs]
- Dave Chappelle: Then I can say a whole story.
- Dave Chappelle: [Back to blues song] My baby left me. My car broke down. I lost $20 and it can't be found. I got issues. That's right, I'm bad as shit. That's right, I got more problems than I can count. That's why I say fuck you.