Chappelle's Show (Comedy Central)
Air date: 7/23/2006
Few shows in their prime have ended with as much disappointment as Chappelle's Show. Just as athletes rarely hang up their cleats in their prime, hit TV shows don't often make a voluntary exit, especially not after two short seasons. Dave Chappelle's reasons for stepping away from his show are well-documented and pretty hard to argue with, but that doesn't mean that anyone is ready to look back at what could have been and not hurt at least a little bit.
Chappelle's Show ended with three awkward "Lost Episodes" that aired almost two full years after the conclusion of the second season. Though Chappelle is physically in the sketches that end the series, his spirit isn't anywhere to be found. The interludes are awkward, the sketches rough, uncurated. In his thoughtful, melancholy analysis of the Lost Episodes over at the the A.V. Club, Ryan McGee describes the beginning of the "Lost Episodes" with a sentence that sums up the entire ill-fated third season: "Neither [Charlie Murphy nor Donnell Rawlings] seems quite sure what to do, so they simply throw things over to one of the few sketches completed before Dave's departure." Sad, man.