With seemingly every comedian of a certain age getting a show on Comedy Central to do with what they will (Inside Amy Schumer and Kroll Show being the most successful, but Gorburger, @midnight, This Is Not Happening and The Jeselnik Offensive also qualify), none stem more logically from that comedian’s prior body of work than Moshe Kasher’s new talk show Problematic. Kasher’s upbringing at the intersection of many different communities has been well documented (particularly in his excellent memoir, Kasher in the Rye). He spent half his time raised by his feminist mother and grandmother in Oakland—while also one of the only white kids in his school—and half his time with his father, a strict, religious jew in Satmar Brooklyn. Kasher was a drug addict and mental patient before getting sober as a teenager and finding a new home in the Bay Area rave scene before eventually becoming a comedian. Oh, and both of his parents are deaf—his delightful mother makes a wonderful appearance on the show’s second episode.

It follows, then, that he’d be particularly interested in how these communities, ideologies and perspectives bump up against each other. His pre-Problematic work reflects that. Kasher has hosted two podcasts—The Champs (with Neal Brennan, who has also, it seems, been granted/earned certain cross cultural permissions) which interviewed black celebrities, and his live Hound Hall Discussion Series, which brings on one expert guest and several inexpert comedians to talk about a given topic (from harems to hip-hop to Brexit to sex and the occult) before throwing to the audience for questions. This same format, more or less, is used for Problematic, which airs its fifth episode tonight at midnight on Comedy Central, and aims to start difficult conversations and address modern concerns within a late night comedy show.

Now, some things have been lost in translation, at least for now. Kasher has been bumped down from an hour-plus podcast length to a twenty-minute TV episode, so you lose what is gained from the playful meandering and the silly tangents within which Kasher and his comedian guests generally thrive. Similarly, no one on those panels seemed to anticipate what they were about to learn from an expert. Everyone could be surprised, leading to some genuinely uncomfortable moments, especially when the audience is given the chance to ask questions of controversial guests (they had some choice words for legendary pimp Fillmore Slim). Perhaps because Kasher plays so well in a loose format, episodes of Problematic are sometimes noticeably edited to cram the discussion into the allotted time.

But these are just growing pains. It’s actually thrilling to watch Kasher find his footing on a larger platform, and Problematic gains a lot in its transition from the Hound Hall format. The presence of cameras makes everything run a bit more smoothly; Kasher freely admits that guests on Hound Hall tend to talk over each other and experts are almost certainly going to be routinely interrupted by comedians. Basically, it’s television, and Kasher knows he can do more with that, using visuals (a hilarious live walkthrough of the dark web) and pre-recorded segments to his advantage in a way you obviously can’t on a live podcast. Plus, Comedy Central’s influence means that Kasher—already scrappy and inventive in getting interesting people for his Hound Hall panels—now has even more access. The expert guests on Problematic are uniformly fascinating, from Reza Aslan to rapper MC Serch, Amna Nawaz of ABC News and the #uncomfortable podcast, and awesome hacker Morgan Marquis-Boire. Finally, Kasher is a consummate host, packing a lot into his quick introductory monologues (he notes Bill O’Reilly’s comments on Sharia law as “ironic, coming from the one man in the world women should wear a burqa around”) and for such a gangly oddball he has a unique ability to put everyone at ease.

Kasher has described Problematic as a Phil Donahue Show for the internet generation, without the irony that you’d think would accompany that pitch. “I say I’m doing a Phil Donahue thing,” Kasher told Pete Holmes on You Made It Weird, “and they go ‘oh, like a satire?’... ’Oh, like a fake one?’ No.” Donahue, who focused on politically polarizing issues between liberal and conservative Americans, would approve. He actually managed to reach across one of the largest divides of the late twentieth century, televising and hosting discussions between U.S. and Soviet citizens via TV-link in the ‘80s. That’s a question Kasher’s critics are quick to ask; is he actually going to be able to reach the people we all desperately need to get through to?

Well, if the members of the Opie and Anthony subreddit are any indication: um, no? Here are a few responses from that crew, some reacting to the pilot of Problematic, and others reacting to the idea of it. (If you don’t want to read some real horrible bullshit, I’d skip this part). Ahem…

“...this made me more sympathetic to the Alt Right than the Richard Spencer speech at Auburn I watched today.”

“You’d just have to look through his twitter to see hes a typical LA fa—ot.”

“The only stuff I can stand to watch on their awful network anymore is South Park and Tosh. Tosh obviously isn’t great but I’ll take anything I can get that doesn’t follow the pc fa—ot rules apparently every comedian thats on tv is supposed to follow these days.”

“’minorities’ can just say fuck whitey cause slavery and vague anecdotes of institutional discrimination?”

“why are jews doing this? don’t they know how this turns out?”

“Guilty white people and guilty white men are the ones who deserve a fucking hollow point to the brain stem.”

Cool! Nothing too surprising there, but what sucks is that that response is enough to make some people say ‘okay, a good try but it didn’t start the conversation, didn’t work, better luck next time.’ To those people: The pilot of a show on a major basic cable network came out of the gate discussing cultural appropriation and bringing on voices to clarify what it means and how it affects people. That’s a massive leap forward. Plus, the fact that this is an uphill battle isn’t new to anyone, least of all Kasher, who knows exactly what he’s doing.

Kasher is starting where he thinks he can gain the most ground, finding necessary conversations to start among people who might think that they’re already on the same page. The “Islamaphobia” episode dives into contention amongst liberals surrounding Islam, and another episode has Nicholas Carr, Baratunde Thurston and Alexandra Katehakis—three intelligent, reasonable people with subtly different views on the internet—approach the topic from different angles, challenging them himself when he isn’t satisfied with an answer, and always guiding the conversation towards someone’s relatable personal experience. Reddit might think he’s preaching to the choir, but of course he’s not. It’s less bombastic than that.

Plus, the second episode (“Is Technology Ruining Our Brains”) adds variation to what people might perceive as an unbroken string of ‘woke’ topics (not that he wouldn’t, in these times, be completely justified in doing just that). This isn’t an example of Kasher not wanting to alienate a potential audience that might be reticent about his approach (cough Opie cough and cough Anthony). This guy doesn’t give a shit. In fact, he’s managed to positively reclaim the one vaguely admirable trait the internet shitlords possess: a giddy joy in provoking the opposition, a quality in Kasher that somehow co-exists with his more diplomatic side without trouble. (Take the topic of tonight’s episode “The Liberal Case for Guns,” which I suspect will back up this point). No, Kasher has tried to cover ground in as many quadrants as possible in a few short weeks because he wants to see the show grow into a something that could cover anything, jumping in between disparate topics the way its ever-changing opening credits do, with unlikely subjects brought up as suddenly and freshly as they were on Hound Hall. That’s where Kasher’s initial vision is going to come to life: a show of genuinely uncomfortable considerations and confrontations between diametrically opposed ideas.

If a season renewal should go to someone, let it go to Kasher, who, having lived half a dozen lives before this one, knows how to play—and is playing—the long game. These first few entertaining episodes are just the opening moves. Plus, with Problematic airing in a block of Tuesday night shows that starts with tosh.0 and ends with South Park reruns (the two shows the Opie and Anthony subreddit thinks are still worth watching), who knows? It might just hit someone at the right time.

Problematic with Moshe Kasher airs Tuesdays at midnight on Comedy Central.