‘That Damn Michael Che’ Wants to Be the Next ‘Chappelle’s Show’

On any given episode of Saturday Night Live, the “Weekend Update” segment, hosted by Colin Jost and Michael Che, is either the sharpest or the most painful part of the night.

Part of that is owed, of course, to the almost impossible production schedule of a weekly TV sketch show meant to be topical and lacerating up to the minute of its 11:30 p.m. launch—a challenge that’s especially evident when it comes to Jost and Che’s weekly news desk outing. But that can also—and frequently—be owed to their comedy’s wild spectrum of taste level, provocation, so-called “wokeness,” and tried-and-true late-night edginess.

That can get the pair in trouble with the think-piece crowd. It can sometimes be almost unforgivably unfunny. But also, that’s just the job. Just as often, the content lands in that zone where the audience gasps, claps, and even thinks for a minute because the joke’s insight was that good.

That happens especially when Che is making commentary about race, injustice, and the reality of the Black experience in America, something still new in SNL’s storied history. And it’s certainly not been done before with Che’s frankness, which often speeds too far ahead of the P.C. patrol for them to catch up.

That’s to say that, however you feel about the endless discourse surrounding SNL’s quality, there’s reason to be intrigued by Che’s new HBO Max comedy/sketch series That Damn Michael Che. Premiering Thursday night on the streamer, the six-episode series centers a different theme each episode, like police brutality, racial profiling, unemployment, falling in love, and more.

Che offers insight on each topic in a format that’s part-stand-up and part-storytelling. His conversational musings bookend a series of sketches on those same issues, in turn revealing his own perspective on the experiences. As he says in the trailer, “It might be uncomfortable to watch.”

There are elements of the series that will inevitably draw comparisons to Chappelle’s Show, particularly in the sketches that use broad comedy to make a statement about the realities of racial injustice in America. It’s a more micro approach than the underrated Wyatt Cenac’s Problem Areas, which spent entire seasons exploring multiple facets of one social justice issue through Cenac’s comedy perspective.

But That Damn Michael Che has a similar effect as Problem Areas. The comedy and the intimacy of Che’s personal experience create a show that feels funnier, more resonant, and more current than he could ever hope to be on SNL.

There’s also reason to be exasperated by how Che has handled himself as a public figure since gaining fame on the sketch show. When called out and criticized for offensive jokes perceived as transphobic, homophobic, sexist, and ageist, he has in the past taken to social media to harass those lobbying the complaints. In one case, he doxxed former Daily Beast writer Samantha Allen after she wrote about transphobia in comedy.

Because That Damn Michael Che asks for a certain level of empathy as he details so much of his personal history and feelings, that behavior is something to square with when you watch. Che clearly thrives on baiting controversy and then engaging with the fallout. And That Damn Michael Che certainly pokes the bear. But what the show wants to say and what Che wants people to glean from its provocations also, then, indicate the humbling of a maturing comedy agitator.

Che’s mischievous streak is undeniably appealing. It’s his biggest asset on SNL. And it carries through to his new series: as he told Seth Meyers this week, he originally wanted to title it That Black Ass Michael Che, with the fantasy that should it ever win an award, the presenter would have to announce, “The winner is ‘That Black Ass Michael Che.’” (He also relayed a story about gifting Jost a Minnesota State Trooper uniform for his birthday, a few weeks after the police killing of George Floyd. The card read, “Dress for the job you want.”)

The so-called “danger” of his strain of humor is necessary for a show like this, and it succeeds when it does push the envelope.

The premise of the premiere is that Che gets stuck in an elevator with a white woman, who can’t help engaging him in a conversation about the police.

“Everywhere I go now, for whatever reason, every time I see a white person, they’re like ‘Black Lives Matter! Black Lives Matter!’” Che says at the beginning of the episode. “They’re so excited to tell me. It’s very strange. I don’t know how to respond. I’m like [mimes tipping his hat], ‘And a Black Lives Matter to you?’”

The episode highlights the fine line culturally we’ve walked between good intentions and privileged, arguably abusive, and triggering behavior. Che’s SNL co-star Cecily Strong plays the white woman, bringing extreme Girl You Wish You Didn’t Start a Conversation With at the Party energy to the sketch, except for the harsh truth that no one started a conversation with her. Throughout the whole scene, she unknowingly weaponizes her white guilt. Her first words to this stranger when the elevator gets stuck: “I just want to say I’m sorry!”

Other sketches include a PSA from the NYPD about steps a Black person could take to not get shot by police. For example: “Please don’t do something dumb like trying to run away from us. We don’t get paid to run.” There’s compassion there too, though! “We know that being pulled over by police can be a big ole pain in the neck,” says one cop. Adds another: “Literally.”

An SNL-like fake commercial advertises a special Protest edition of a FitBit that tracks your heart rate and your real-time contribution to social change. (When it’s time to apologize to a member of a marginalized community, it sends an alert.)

Another episode centers on the different ways Black people fear death, and how they deal with that fear. It’s profound, enlightening stuff, delivered with Che’s matter-of-fact smugness. That attitude of his makes the power of his jokes sneak up on you. It also makes the ones that miss their mark—jokes about getting raped in prison and prostate exams being emasculating land with a hollow, antiquated thud—all the more noticeable.

That Damn Michael Che is making the most of a chance to do something different with comedy at a particular cultural moment. There are people for whom that title will be whispered in awe-filled praise: “Wow, that damn Michael Che…” And there are critics who will deliver it as a curse: “Ugh, that damn Michael Che…” That alone should make the show worthwhile.