It's a sunny Sunday afternoon in Silver Lake and Moshe Kasher is showing me how to buy heroin online. Lounging in a leather armchair in his country-style living room — which is accented with splashes of bright-orange paint and whimsical wallpaper — the 37-year-old comedian downloads onto his MacBook free software called Tor, an internet browser that acts as a portal to the so-called "dark web," the untraceable network where people from all over the world allegedly go to shop for sex, drugs and murder using Bitcoin. Kasher isn't looking to buy any of these things — and he hasn't committed any crimes by simply downloading the software — but he's fascinated by the idea that this kind of black market exists, and that it's accessible to nearly anyone with an internet connection.
"It's one of the last taboos that we have," says Kasher, who wears round tortoiseshell glasses and an unruly, pompadourlike mane that's tucked beneath a baseball cap with the letter M on it. "Everybody knows about the dark web, but everybody just assumes it's child pornography."
"But it's so much more!" Natasha Leggero chimes in from the piano bench where she's perched across the room, her voice mimicking the enthusiastic tone of a pitch woman in an infomercial. "Christmas in Prison," the folksy John Prine love song about missing his sweetheart while serving time, plays softly in the background. Leggero, wearing a short silk robe and cradling one of the couple's three Chihuahua mixes in her lap, turns from playful to serious. "You're really going to do it now?" the actor-comedian asks her actor-comedian husband, pointing out that he'll have to fill in the captcha, like, 20 times.
But by now it's too late: Kasher has already mastered captcha jiu jitsu (although Leggero was right; it took him several tries) and is staring mesmerized at his laptop screen. "OK, check this out. Boom!" he says, scrolling through dozens of customer reviews — "fast delivery, good quality" — for substances including heroin, LSD and MDMA on a site known as the dream market. "So what kind of drugs do you guys like?" (For the record, this was all for research purposes and no drugs were purchased.)
Kasher learned to use Tor three days earlier during a test run of his forthcoming Comedy Central series, Problematic With Moshe Kasher, a late-night talk show that, as its name suggests, might offend some viewers just as easily as it entertains others. During the live test show at Upright Citizens Brigade, Kasher and his guests — two comedians and one investigative journalist — logged onto the dark web and explored it onstage while taking questions from the audience, which may have been a first even for the typically anything-goes comedy theater.
The dark web is just one among the many topics Kasher plans to explore on his weekly half-hour series, which premieres April 18. Other themes might include cultural appropriation, fake news, border towns, safe spaces versus free speech on college campuses and the left versus the left (e.g., the Democratic Party versus the Democratic Socialists of America) — essentially everything Americans might not want to but probably should be discussing at a time when the country is incredibly politically polarized.
"I think people are really desperate for conversations," Kasher says. "I'm really fascinated by the idea that at the same time, the internet is sort of expunging our attention spans."
As inspiration for his own series, Kasher is taking cues from the zanier talk shows of the pre-internet era: The Dick Cavett Show from the 1970s and The Phil Donahue Show, which ran from the '70s through the '90s and often mined sensational subject matter using an audience-driven, improvisational interview style. Some of Donahue's episodes, such as one uploaded to YouTube called "Mulattoes Who Pass for White," undoubtedly would be considered problematic by today's standards, but the show's candidness also occasionally produced insights that are still relevant decades later. Kasher says he reached out to Donahue, or, as he calls him, "the spiritual godfather," via his publicist in an attempt to ask his advice about hosting a talk show, but never heard back.
"Donahue was almost stumbling his whole career into these conversations, but obviously he was doing it [purposely] so it wasn't a stumble," says Kasher, who is looking to explore similarly uncomfortable subject matter on his own show, often drawing from the spontaneity of crowd work — something he's known for in his stand-up. "I think going to the audience is the interesting elixir that's going to make this thing unique."
Kasher has had plenty of experience leading contentious conversations as the host of the Nerdist podcast Hound Tall — the name is a spoonerism for "town hall" — which regularly tapes at UCB, his preferred grounds for experimentation. The show has recently featured guests such as Leggero, Silicon Valley's Kumail Nanjiani and porn star Conner Habib. Each episode starts as a highbrow intellectual debate but often dissolves into a raunchy comedy roast over charged topics such as the Electoral College, Brexit and the case for ending civilization. Kasher also previously co-hosted, along with Chappelle's Show co-creator Neal Brennan, the decidedly un-PC podcast The Champs, on which the white hosts interview black people. That show ended its 4½-year run in early 2016.
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But Kasher's brand of smart, wildly unapologetic comedy has also provoked fierce criticism. His 2012 Netflix stand-up special, Live in Oakland, got him listed on the Tumblr blog Your Fave Is Problematic — a term favored by liberals to critique a public figure who may also be potentially racist, sexist or homophobic — for his jokes about Jews, Muslims, fat women, black people and just about every minority group in between. The blog post still bothers Kasher, a self-described political leftist who was born in Queens, spent summers in Brooklyn with his Hasidic father and was raised by his mother in Oakland, where he remembers being brought to gay rights marches and Gulf War protests.
"I've been politically radical my whole life, so when the left attacks, that hurts more," Kasher says. At the same time, he adds: "I'm not trying to make my show a vehicle for the left. [John] Oliver's the best that's been doing this version of [a] show."
If his previous projects were considered problematic, sometimes bashed by critics both progressive and conservative, then Kasher has decided to own up to — and double down on — that label by naming his new talk show after it. Problematic With Moshe Kasher will air just months after Americans elected the most trolling and unabashedly un-PC president ever, but it would be too easy (and exhausting) to make that the focus of every episode. "I don't want Donald Trump to be the head programmer of my show," he says.
By now, it's midafternoon and Kasher's once-tranquil home has become loud and chaotic. There are painters asking his feedback about the work they're doing in another room, Leggero has resumed her complaints of hunger that began nearly two hours prior — she suggests burritos at Al & Bea's Mexican Food — and all three of the couple's small dogs, Pablo, Cutie and Blanche, are yipping and barking in unison. The most problematic subject in their household, if only for this brief moment, is what to eat for lunch.