The connection between improvisational comedy and improvisational music is on display throughout the film. At one point, Chappelle observes that "All comedians want to be musicians, and all musicians think they're funny" and later advises aspiring comedians to listen to Thelonious Monk to learn about timing. Watching Chappelle improvise on stage or in a back room, telling jokes over slow drumbeats, the parallel is undeniable (as is the fact that he's most likely stoned out of his gourd).
Block Party has some great moments, and tends to be at its best when Chappelle' comedy comes together with the great music on display. For instance there is a great game of musical Simon-says with The Roots giving Chapelle a James Brown-style stinger every time he says "hit me," despite the comedian' best efforts to screw them up. Another great moment comes when Chappelle tells momma jokes to Mos Def, who keeps time on the drums, their banter lending the whole affair a playful, breezy vibe.
Throughout the film, Chappelle is in complete control of the audience, not only at the actual Block Party, but the audience in the theater as well. There' no hint of the tormented, reclusive, paranoid guy that supposedly killed Chappelle' Show, just the easy, ambling comedian that audiences love, making observations in his flat Midwestern drawl and smoking what is quickly becoming a trademark cigarette.