
The top distinction may belong to the time he inked a deal with ABC to star in the Home Improvement spin-off series called Buddies, based on a 1995 guest appearance in the Tim Allen vehicle by Chappelle and collaborator Jim Breuer.
The series lasted just six episodes on air before ABC mercy killed the dumpster fire, and Dave has spent the last 26 years distancing himself from the disaster while trying to prevent the footage that remains from ever seeing the light of day. Buddies is to Dave Chappelle what “The Star Wars Holiday Special” is to George Lucas if 20th Century Fox slapped George’s face on the DVD cover and marketed it as “The Special George Lucas DOESN’T Want You To See!”
It all started when Dave Chappelle and Jim Breuer made a guest appearance on Home Improvement playing two “Tool Time” audience members whom Tim pulls onstage to discuss their relationship issues. The scene is a classic 90’s sitcom men-versus-women segment that revolves around Tim teaching Dave and Jim how to avoid getting nagged.
The duo had chemistry, with Dave being the obvious stand out star. The episode was well received by critics and audiences alike, and as Home Improvement wrapped up its fifth straight year dominating network TV ratings, Walt Disney Studios and ABC were itching to double dip on its success.
The plan was hatched to launch a spin-off series featuring Dave Chappelle and Jim Breuer playing the same pair of friends who captivated Home Improvement viewers in their brief, four minute cameo in the previous season. Much like another catastrophic ABC flop, the decision was inexplicably made to center the tone of the show around a lighthearted discussion of race relations in America.
Basically, one guy is black, one guy is white, and they’re friends. They make jokes about the differences between black guys and white guys. That’s pretty much the whole show.