Dave Chappelle has never been the type to do things the conventional way. In 2005, he abruptly abandoned the third season of Chappelle’s Show and took an extended, unexplained trip to South Africa. It shouldn’t have been much of a surprise, then, when he announced that he would return to Toronto for three shows with just two weeks’ notice.

Still, the Aug. 20-22 Winter Garden Theatre shows sold out in a hurry, demonstrating the funnyman’s sustained popularity seven years after his last true mainstream exposure. In honour of Chappelle’s surprise return, we list some of his funniest moments.

Kramer

Four years after Michael Richards’ racial tirade at The Laugh Factory, Chappelle riffs on the former Seinfeld star — and speculates about his own mental health – in this funny clip.

 


Racial Draft

Want to see race turned on its ear? Take eight minutes out of your day to catch this great clip envisioning what a “race draft” would look like, complete with commentary. This was one of the signature bits from the comedian’s Chappelle’s Show days.


 

Police Brutality

Part of his hit comedy special “Killing Them Softly,” Chappelle addresses racial stereotyping on behalf of cops in L.A. His “white” voice still gets us to this day.

 

Sesame Street

You’ll never see the iconic PBS children’s series in quite the same way after hearing Chappelle’s hysterical take on it. Poor Oscar!

 

I’m Rick James, Bitch!

This top five wouldn’t be complete without the most popular bit in the short history of Chappelle’s Show, and that legendary, oft-quoted line. Its popularity still lives on and holds up across second and third (and 27th) viewings.

Dave Chappelle, Winter Garden Theatre, 189 Yonge Street, 416-314-2874. Aug. 20-22