12 Great Hip-Hop Guest Appearances On ‘Chappelle’s Show’

Dave Chappelle is Big Boi’s Annoying Friend

We all have that annoying friend that we dread talking to when we pick up the phone. Inevitably, you will be invited to some event that you have no desire of attending but will feel guilted into going because either you can’t come up with a reasonable enough excuse or because you don’t want to hurt this person’s feelings.

In this sketch, Dave is Big Boi’s annoying friend that he would like to avoid. After Chappelle had lost his show to his hated rival, Wayne Brady, Dave finds himself with too much free time to spare and calls to see if Big Boi wants to come out and hang. Big Boi registers that moment of annoyed disgust when he realizes that Chappelle is on the other line and offers a ridiculous excuse to avoid hanging out: Tennis with Don Cornelius on the Moon.

Later in the sketch, sort-of rapper, Nick Cannon, shows up to taunt Dave about his status as Chappelle’s son favorite comedian.