Dave Chappelle and Jon Stewart offer a masterclass in social comedy


It may be futile to attempt to fully describe what Dave Chappelle and Jon Stewart did this week at the Wang Theatre, so let’s just focus on Monday night (June 11), the first of three nights (and the first of five shows) the tag team spent on Tremont Street.

So we’ll offer up this: Sweet baby J, what a night.

Providing a three-hour masterclass on how to effectively unite brutally honest social commentary with your recommended daily dose of dick jokes and religious humor, the pop culture icons brought the Wang to a roaring Standing O on a number of occasions, while keeping them on the edge of their seats for the duration of the evening.

And they had some rather unexpected help kicking things off.

By the warm welcome he received, you never would’ve guessed that Michael Che, who surprised everyone as he stepped onto the stage as a guest opener, had been all but shunned by the city of Boston after he pointed out the city’s racist history during a set at Boston University last March. To reciprocate the roaring applause, the Saturday Night Live star doubled down on his original claims about the city, but a lot has changed in the last year. After asking “How did you guys not know?”, Che was greeted with a significantly light-hearted applause. (In case you’re wondering, he’s back at The Wilbur on June 30.)

Of course, that was just a warm-up. If desire can be accurately gauged by applause, or a nearly earth-shattering ovation in this case, Jon Stewart — who is by no exaggeration largely responsible for lighting the socially-conscious fire under young America for the better part of the last decade — journeyed from his post-Daily Show cave to deliver exactly what the crowd wanted and needed on Monday night, in what feels like such dire and confusing Orwellian times, where the viewpoint of the now-gray haired satirist would be most appreciated. Once the pandemonium over his return died down, Stewart dove beard-first into a slew of topics, ranging from the background of his 2016 Twitter fight with Donald Trump to how painfully easy it is to legally buy a gun in the US.

But it wasn’t all doom, gloom, and inept world leaders for Stewart, as he channeled his material from his political comfort zone to family life, raising kids, and the frustration of growing up in a Jewish household during all the fun Christian holidays, which had the crowd bellowing their approval for the entirety of his set. His confidence oozed through the PA system, but that level of confidence and undeniable ability to grip to the crowd would be closely challenged by what was lurking just behind the curtain at stage left.

Taking the stage with his fist in the air and a rock star’s swagger, Dave Chappelle exuded a type of confidence so potent, that it made attendees forget about the fact that they were completely disconnected from the outside world, as they took their gaze off their phone-concealing Yondr bags a little more with each hearty laugh. Further cementing why he’s widely considered today to be stand-up’s GOAT, mixing hard-to-swallow truths with the same unrestrained brand of observational comedy that attracted his droves of fans to him all those years ago, a muscular-framed Chappelle ran the gauntlet on a laundry list of topics, most memorably a filthy scene-by-scene description of a Chuck Berry sex tape, all the while reserving the set-up to nearly every knee-slapping punchline for some sort of genuine and thought-provoking sentiment about the state of the country, ranging from school shootings to racism to the #MeToo Movement. We’re not going to spoil any of it; we’ll just recommend seeing it for yourself as soon as possible.

A post-show sit-down followed a child-like dramatization of Trump and Kim Jong-Un meeting at their summit, where the two chased each other around the stage until Stewart stepped on Chappelle’s ashtray he had placed on the floor. Featuring the trio of the night’s performers, as well as host Wil Sylvince, the “after hours” bull session marked an informal return of sorts of Stewart’s Daily Show Q&A format, as he asked Che and Chappelle their thoughts on an array of social topics, offering an even more in-depth look into the minds of some of comedy’s most beloved and respected figures.

On paper, what transpired at the Wang Theatre on Monday night was many things. It was fun, oftentimes filthy, and above all else — for all intents and purposes — an absolutely legendary bolt of commentary for our crazy and unimaginable times.

Featured image by Jason Greenough; follow him on Twitter @DadBodVanilla.