Comedian Moshe Kasher on His Deliberately ‘Problematic’ Talk Show

In his new Comedy Central talk show, Moshe Kasher takes on the thorniest topics of our time through humor, wit, and in-depth conversations

It’s early on a Thursday evening in April and a slightly nervous-seeming Moshe Kasher is making sure everything is ready to go before he tapes an upcoming episode of his new Comedy Central talk show Problematic. The host mingles with friends that include Nick Kroll, who will appear as a guest on the show, and comedian Ali Wong, who’s there to watch and support from backstage. The studio audience is arranged in a full circle around the small set, only a few rows deep so that no one is too far from the stage.

Each episode of the new show will be dedicated to a singular “problematic” theme — the first one is cultural appropriation. Unfortunately, the ill-fated Pepsi protest ad had not yet debuted when Kasher taped what will be Problematic’s premiere episode. (“Don’t I wish,” he jokes.) Instead, he talked to Black-ish creator Kenya Barris about what it means for white people to co-opt black culture.

“The worry with a topic like that is that it’s so fraught with people’s ideological baggage that you won’t be able to make it funny,” Kasher tells me by phone the day before the show’s April 18th premiere, “but so far that’s been the fun of the show.”

Standing in front of a large screen, Kasher opens each episode with a multi-media monologue in the style of Full Frontal's Samantha Bee, but in his dogged efforts to get inside a specific issue, the late-night host he most resembles at the moment is John Oliver. Except instead of sitting behind a desk for 30 minutes, as that HBO host does, Kasher moves around — a lot.

“I’m definitely feeling like a plate-spinner up there,” Kasher says, describing the challenge of trying to keep the conversations on the show both meaningful and funny at the same time. “It’s very hard to have your own show,” he jokes.

The life of a talk show host is a new one for 37-year-old Kasher, who was born in New York but grew up in the Bay Area and now lives in Los Angeles with his wife and fellow comedian Natasha Leggero. After years of popping up as a guest on shows like Chelsea Lately and @midnight, Kasher is ready to show the world what his version of a late-night talk show is. It turns out, it looks a lot like a daytime talk show. As Kasher said when the show was first announced last fall, he sees himself as “the Phil Donahue of the Internet Age.”

With that role model in mind, Kasher ventures into the audience during each episode to hear from both invited experts and regular people who might have something to say about that episode’s topic.

“The biggest challenge is the audience interaction, which is also the most unique part of it,” he says. If there is a screening process for this segment, it is going to need a bit more fine-tuning: most people Kasher walked up to on the night I visited either didn’t have a lot to say or were trying to sell something.

Kasher says he thinks audience members “could get more” instruction ahead of time in terms of what makes a compelling comment or question on television. “For sure that’s the thing I can tell will get better, I knew that the first day,” he says. “How do you get people to understand that if they give a five-minute diatribe on the issue they’re most charged up about that probably it’s not going to make the cut?”

For the taping of the premiere, Kasher invited a Native American community leader to come and talk about his experience with cultural appropriation. “He gave this really beautiful, impassioned, powerful speech and then I, this white guy, had to ask him, ‘Do you think you could just distill the last thousand years of native oppression and suffering into kind of a sound bite?’ That was a very weird position to be in, but it had to be done or that wouldn’t have made the cut.”

The decision to call the show Problematic stems from Kasher’s own experience being labeled that word by a supposedly liberal critic who took offense to several jokes in his 2012 stand-up special Live in Oakland. So what does “problematic” mean to him?

“I think that the word means ‘you have engaged in a behavior that I find worthy of shame,’” he says. “The line of it is so wildly different for everybody. That’s why we wanted to call the show Problematic, because the whole thing is about the varying lines that we walk.”

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“One of the main principles of the show is, just because you disagree with me doesn’t mean I won’t engage in the conversation with you,” he continues. “So hopefully the show will be ‘problematic’ in a good way — engaging and challenging.”

His fears that heavy topics like cultural appropriation will be too hard to make humorous are mostly unfounded in the first episode, thanks to Kasher’s uncanny ability to drop improvised jokes into the mix at every possible opportunity.

In the exclusive clip below from Tuesday night’s premiere, his guest Kenya Barris talks about the experience of realizing that his own “black-ish” kids had white friends who were “more black” than they were. Kasher gets a laugh by simply pointing to himself and nodding in response.

In this time of heightened awareness of the various “bubbles” we live in, Kasher says he wants the show to help bridge those gaps in any ways it can. “When people disagree with each other is when they stop talking. And I think that’s actually the time for the conversation to begin,” he says. But that doesn’t mean he’s out to start arguments.

“My primary point of doing the show is not to find people that I can fight with, but in fact have conversations that I find interesting and substantive and fun,” he adds. “It’s not like a Jerry Springer, mud-slinging show, as much as it is a deep dive into conversations.”

But the tapings have produced some genuine Jerry Springer-esque moments, including when Kasher tried to talk to one woman in the audience but another man across the set kept yelling out his thoughts on the matter. For a moment, the comedian became part referee, part matchmaker, and you could feel some of the dynamic energy that can come from truly unscripted television.

“Hopefully that will continue,” Kasher says of the time he nearly lost control of his own show. “I’m still waiting for the moment I can kick someone out, that will just make my life.”

For tonight’s taping, the topic is how the internet is changing our brains. Following a panel discussion that Kasher kept moving and alive with quick-witted jokes and a hilarious field piece in which he talked to post-millennial teens about their relationships with their phones, the show ends on a surprisingly sentimental note.

Kasher sits down for a sign language conversation with his mother, who is deaf. After an episode that mostly focused on the downsides of technology, we learn how much the internet has improved her ability to communicate. The short video makes us completely rethink everything we’ve just seen in a profound and unexpected way.

“I feel like art and sentimentality is really missing from comedy,” Kasher tells me, adding that part of the “power” of his memoir Kasher in the Rye, which tells the story of how he became a teenage drug addict, is that it “doesn’t shy away frightenedly from things that would make you feel stuff.”

If Kasher can continue to present nuanced moments like this one, he has a better chance of getting people to think outside of their closed-minded bubbles on any number of issues plaguing our country right now than some of his more outraged late-night peers.

“What is life if you’re not laughing, thinking and feeling?” he asks, optimistically. “And hopefully my show will make you do all three.”