The NY Times' Jason Zinoman traveled to San Francisco to watch Dave Chappelle do a secret stand-up gig and wrote a piece about it. This is all in the wake of Chappelle doing two shows in NYC with Chris Rock, spurring speculation about a comeback. Chappelle talked about making a comeback twice during the SF show but didn't get too specific, so maybe he's plotting something big.

Lost Roles is a weekly column that takes a particular comedic performer or writer and dives deep into all of their movie and TV projects that came close to happening but didn’t, for one reason or another. This week, we turn our attention to Dave Chappelle, who eight years ago was the hottest comedian in the country.
After spending more than a decade honing his chops as a stand-up comedian and appearing in supporting roles in other people's movies (and a starring role in his own, Half Baked), Dave Chappelle finally found the perfect vehicle for comedy in the Comedy Central sketch show Chappelle’s Show in 2003.
Chappelle’s [...]

Chappelle's Show is unlike almost any sketch comedy show before it. It doesn't come from the same sketch comedy tradition that SNL and Monty Python created; it's first and foremost a vehicle for Dave Chappelle. He and his co-writer Neal Brennan wrote every single sketch and Chappelle stars in almost every one. Although there are regularly featured actors like Charlie Murphy and Donnell Rawlings, there really is no permanent cast to speak of. The show really has more in common with vanity driven sitcoms starring stand-up comedians than any other sketch show in terms of it's approach to humor. Despite this, or perhaps because of it, the show became [...]