A couple of moments stand out from the first night of Dave Chappelle and Jon Stewart’s joint stand-up comedy shows, which started its limited three-city run in Boston on Monday. The first concerns just how, in the words of the former The Daily Show host, “lucky” everyone in attendance at the Wang Theatre was. He wasn’t wrong, for not only was the process organized by Ticketmaster’s Verified Fan program deceptively simple, but patrons able to successfully purchase tickets were treated to a unique, three-hour riff session between the co-headliners, special guest Michael Che and opener Wil Sylvince.
Another moment that stands out from the otherwise lengthy night of comedy is Chappelle, Stewart, Che and Sylvince’s time onstage together for the final hour of the evening. When the Chappelle’s Show co-creator concluded his set, Stewart joined him on stage for what many in the crowd thought was a joint goodbye. (Some were already heading down the aisles toward the exits.) But as anyone familiar with the Netflix comedian’s Radio City shows can tell you, finishing a planned routine isn’t enough for Chappelle. Most road comics are more than happy to grace their fans with an encore, and he didn’t disappoint.
After Stewart again highlighted how unique the group’s onstage banter was, Chappelle reminded the crowd that the cell phone ban was his idea. “I did the phone thing,” he quipped, “because this is going to be a special thing. This night, there won’t be any other night like it. I want everyone here to know this, and enjoy it for what it is.” By the end of the extra hour, the truth of Chappelle and Stewart’s sentiment rang true with most of the show’s attendees, as well as the four comics onstage. They joked about news items Sylvince read aloud from his phone, teased one another constantly and generally had a good time.
Yet there was also a thick layer of seriousness to the affair. When Chappelle and Stewart did their respective sets, the tension was palpable at times. This makes perfect sense, considering the latter used to host a pre-fake news “fake news” program and the former’s most recent special earned him plenty of scrutiny over its decidedly problematic #MeToo and Time’s Up comments. It also makes sense because of their mutual friend, Louis C.K.
In July, HBO announced that Stewart would be making his triumphant return to stand-up with a brand new special 21 years after 1996’s Unleavened. He kick-started things with Night of Too Many Stars in November, then promptly launched into a smattering of stand-up gigs here and there to prepare. The most recent before this tour was an appearance at Comedy Central’s Clusterfest in San Francisco, where he joked about his intent to “finish” Donald Trump. Sure enough, Stewart opened the show with a play-by-play of the infamous 2013 Twitter feud with the reality TV host. He also had no problem condemning Trump’s blatant sexism.
Gun ownership (via a wonderfully clever setup) and parenting were also choice topics of his, thereby providing a road map to what Stewart’s HBO special will look like. Even so, C.K. hung like a shadow over the set. Before the New York Times expose, the comedian had been a part of Stewart’s Night of Too Many Stars, but he was quickly removed from the roster thereafter. When asked about it at the time, the host said he was “stunned” and admitted “comedy on its best day is not a great environment for women.” During the show, the subject came up very little — again, unless Trump was the target.
Then Chappelle directly addressed his controversial comments from The Bird Revelation, the last of his four Netflix specials in 2017. “I said some things about one of the victims that a lot of people didn’t like,” he said. In the special, he acknowledges the accusers were “right” while noting the response — C.K. losing massive deals and projects — was “disproportionate.” He then targeted Abby Schachner, who said the comic’s misconduct left her “dispirited” and “discouraged her from pursuing comedy.” Chappelle’s response? “That is a brittle-ass spirit!”