Comedian Dave Chappelle ended his sold-out, three-night run at Toronto’s Winter Garden Theatre on Wednesday, Aug. 22, on a bizarre note, backed by one of the biggest pop stars in the world.
After two evenings of warm-up music provided by Future the Prince, night three featured Drake instead, though Future remained onstage. Drake spun some obscure R&B and hip-hop, which was often subdued and muffled, but kept his and Future’s heads bobbing appreciatively.
Unlike Tuesday evening, when Chappelle incorporated Future into his set with playful asides and an elongated outro featuring Jay-Z’s “Jockin Jay-Z,” Drake never said a word on Wednesday. He and Future just laughed along with the rest of us, as Chappelle delivered a brilliant hour and 20 minutes of standup, much of it completely unique from the night before.
Chappelle riffed about meeting Toronto Mayor Rob Ford for a discussion about the city’s smoking bylaw (after word leaked about his onstage puffing on Monday, Chappelle was banned from smoking indoors for the next two shows). He also implored Canada to toughen up its image, starting with our flag and national anthem, and he discussed his personal life with great openness and bravado.
As the stage manager flashed a light to say his time was up, Chappelle slowly seemed to be winding down when something snapped. “There’s something weird in the air tonight,” he had observed earlier. “It’s like there’s something being left unsaid or something.”
That intuition (and Chappelle's compliance) led to a prolonged and, for some, frustrating "Q&A" at the end of the show. Audience members yelled out bewildering things like the names of characters from Chappelle’s Show, and requests such as “Talk about rap music!” “Make Half Baked 2!” “Ask Drake about Chris Brown!” and, most profoundly disturbing for Chappelle, “Are you happy?”
The crowd booed loudly at that one, and Chappelle made special note of the young woman, saying, if she could find him in the city later that night, he would personally address the question.
There was a kind of menace in his answer and, from then on, he just glared at the audience, as more and more stupidity rained down from the anonymous darkness. But Chappelle just let it come. Even Drake and a visibly shaken Future (who grinned and laughed all of Tuesday night) sat stupefied at the display. Sure, Chappelle’s retorts were priceless and hilarious at times, but it was also an awkward experience, where he willfully allowed the audience to antagonize and turn on itself.
After an hour of this, which included many false endings, Chappelle said farewell. The crowd gave him a standing ovation, and he gave us two middle fingers for our efforts. He seemed disappointed in us and, even though he pointedly enabled us by not ending the show, he really had every right to be.
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