Stand-up, then a sit-down with Dave Chappelle, Jon Stewart, and Michael Che at the Wang

Dave Chappelle and Jon Stewart
Mathieu Bitton/file
Dave Chappelle and Jon Stewart’s comedy tour brought them to Boston for five shows at the Wang Theatre.

Monday night’s show at the Wang Theatre presented two modern comedy titans, Dave Chappelle and Jon Stewart, in the first of five shows over three nights, and at a generous three hours that included a free-for-all conversation in its final stretch, it would likely stand as the one to see.

Surprise opener Michael Che got the first of several standing ovations for the night, and set the table with a punchy, pointed set for an evening of socially conscious humor and ridiculousness. (Che is not scheduled to appear for the remaining Boston shows.) For any difference in tone or delivery, Stewart and Chappelle share a similar approach to their craft. They think as deeply on a subject as they can, comment as honestly as possible, and make sure at some point, they honk the clown nose with something scatological or silly to remind you it’s a comedy show.

Stewart followed Che. Longtime fans might have recognized some of the opening material. He referred to Boston as a drinking town, wondering if we ever collectively wake up and ask ourselves, “Did we [expletive] New Hampshire last night?” echoing a line he used at a Comics Come Home show more than 20 years ago. He recounted his well-publicized 2016 Twitter fight with Donald Trump, made more surreal because Stewart didn’t have a Twitter account. His most charged material of the night came when he made the surprising revelation that he had purchased an AR-15 rifle, and how tough it was to get one. He detailed the paperwork and how long it took him, and the home visit, before admitting, “No, I’m sorry, I tried to adopt a cat.” Getting a gun, he said, would have been much easier. He ended on material about the joys of parenthood, or as he put it, “a chance to ruin someone from scratch.”


Chappelle is adept at keeping an audience off balance. You know the outrageous statements are coming, but they still land with force, and he was throwing haymakers Monday. The set took breakneck turns from earnest to filthy in bits about Chappelle buying guns to protect his farm, the Chuck Berry sex tape, Louis C.K., and a contemplation of growing up poor. (Legal language on the tickets forbids reviewers to quote Chappelle’s material. He also had audience members stash away their phones in pouches the theater handed out.)

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That should have been the end of the show, but Chappelle and Stewart came back out together for an informal rap session that lasted almost an hour. It started with them wrestling, mimicking the handshake they imagined was happening between President Trump and Kim Jong Un at that moment at their summit in Singapore. Then Che and Wil Sylvince, the show’s host, joined them, and Stewart reverted to a familiar role — thoughtful interviewer — asking increasingly serious questions about race, gender, and politics. The more animated Chappelle got in his answers, the more gravelly his voice became, leading Stewart to note, “The longer you talk, the more you sound like Harvey Fierstein.” Chappelle took the bait and launched into a full-on impression. Honk.

Around 30 minutes in, Stewart asked, “Why isn’t this on Netflix?” Your move, Netflix.

Dave Chappelle and Jon Stewart

With Michael Che. At Boch Center Wang Theatre, Monday night. Repeats Tuesday and Wednesday at 7 p.m. and 10:30 p.m. (Che is not scheduled to appear for the remaining Boston dates.)

Nick A. Zaino III can be reached at