Chappelle's Revenge

At its peak, Chappelle’s Show could have been the funniest thing ever aired despite everyone yelling, “I’m Rick James Bitch!” incessantly for a few months. With most people without DVR or TiVo, it was a show many anticipated and watched in real time. The jokes, quotes, and sketches became part of pop culture moments after they aired and live on despite Dave’s retreat from the spotlight.

After signing a contract for $55 million the wheels fell off for Chappelle. Rumors of friction between Dave and co-creator Neal Brennan surfaced, and things unraveled quickly leaving the show’s third season unfinished. Everything from drugs to Oprah was blamed for the show’s demise and whole story might never been known.

Despite the last season being rough around the edges and largely unfinished, it was still packed with memorably moments including a revenge skit based on the $55 million Dave had just made before season three began.