Is Theo Von podcasting from the right or the left? That depends from where you’re looking.
When he sat with Donald Trump last summer in the run-up to the presidential election, he led a surprisingly affecting and humanizing conversation about drugs and addiction unlike any Trump had ever publicly had. But also: With Gabor Maté, a Canadian physician who has written extensively about the Middle East, the conversation about the thousands of children killed by Israel in Gaza reduced Von to tears.
Is Von compassionate or crude? With the professor and podcaster Scott Galloway, Von spoke openly about his struggles with pornography: “It was the first kind of interaction with women that I could manage.” But also: joking with Grace O’Malley, an up and coming comedian, about her romantic dry spell, Von assured her, “I think there’s a lot of semen heading your way in 2025.”
As an interviewer and the host of “This Past Weekend,” a podcast that routinely garners millions of views and listens, ranking among the most watched shows in the country, Von’s chameleonic chill is both his superpower and his mask. The result is a kind of lenticular effect — depending on the week, he’s a sophisticate or a naïf, one of the bros or a sly interloper.
Von, an aww-shucks 45-year-old with hair somewhere between shag and mullet and a persistent mien of latent mischief, is often lumped into the inelegantly grouped “manosphere,” a loose aggregation of podcast hosts and social media figures — Joe Rogan being the sun of that solar system — whose politics lean rightward and whose attitude is allergic to doubt. They have built, in short order, a parallel mainstream media ecosystem, with personality-driven platforms that often let guests hawk their viewpoints unchecked, creating an echo chamber of boast and brag.
Last month, when Von was a guest on the “Full Send” podcast, hosted by the MAGA-prankster Nelk Boys, he poked at their spacious moral window in regard to booking guests: “Finally somebody that’s not a sex trafficker on here.”
But unlike those peers, Von is pointedly tough to pin down, culturally or politically. His fear-free, lightly oddball and unselfconscious inquisitiveness and his comfort playing with jumbled signifiers — of political affiliation, race, class and more — make him a far more nebulous performer. Under the cover of the manosphere, he’s become one of the defining conversationalists in America.
Theodor Capitani von Kurnatowski III, who describes his heritage as Polish and Nicaraguan, grew up in small-town Louisiana. He speaks often about his challenging relationship with his family (his father was over 60 when Theo was born), and has said he was legally emancipated at 14. His first brush with celebrity came in 2000, as a teenage cast member on Season 9 of MTV’s “Road Rules”; footage shows that Von was already conversant in the same kinds of socially skeptical and laconically self-lacerating humor that still shape his work. He went on to become a stand-up comic.
“This Past Weekend” began in the mid-2010s, in part as a platform for Von to talk about his addiction recovery process. (He has spoken about his struggles with alcohol and drugs, and intimacy disorder.) As it has become an interview destination for comedians, musicians, actors and politicians, Von has repositioned himself as a Forrest Gump-esque Everyman careening his way to the top of American popular culture and democracy. “You’re exceptional at being average,” the right-wing media personality Candace Owens told him.
Rogan, perhaps his closest analog, treats interviews like bouts of conspiratorial one-upmanship; Von’s mode is almost completely the opposite. In his rangy, vibey conversations, he presents as a proxy for the average American citizen, getting bombarded by opinions at all times and simply trying to forge a coherent path through the competing streams of information and misinformation. Last fall, his show went into overdrive, becoming a must visit for politicians and proxies from both parties: Trump, Bernie Sanders, JD Vance, Mark Cuban (stumping for Kamala Harris), Robert F. Kennedy Jr.
But his motivations weren’t purely political. Von said he was partly drawn to Trump knowing that one of Trump’s brothers died of alcoholism-related causes and thought talking about that with him might be revealing.
“You don’t hear a lot about his feelings, Trump’s feelings,” Von told the comedian Tom Green during a recent episode. “And if you do, he doesn’t communicate it in a way where it’s very emotional to people, I don’t feel like. So I was just curious about that.”
Von tried to host Harris and Tim Walz, to no avail. “It was kind of a bummer — I think it would have just let them be more normal,” he told Green, before pivoting to a thought on why the unvarnished world of podcasts is so disproportionately effective. “If something’s too much behind the glass these days, people don’t trust the glass.”
And there is no glass on “This Past Weekend,” which has the anything-might-happen élan of public access television. Von’s interviews generally run around two hours, and can feel even less hurried than that — key to their effectiveness is that neither Von nor his guests appear to have anywhere else to be. A jagged conversationalist, Von sometimes leads with spicy wit, sometimes with curiosity and sometimes with silence. Often he’s holding onto his thoughts — or maybe formulating them — just a couple of seconds longer than is comfortable, nudging his guests to fill the void.
Von’s show, with its afterthought set design (his studio is in Nashville, where he now lives) and unassuming affect, is the antithesis of the canned talk shows that network television has been refining for half a century. And while it’s difficult to compare metrics across platforms, Von’s audience often tops a million views on YouTube, and he competes with the glib performances of the three major late-night hosts — Jimmy Fallon, Jimmy Kimmel and Stephen Colbert.
He can draw on a wider range of guests, as well. After the wave of social-media “cancellations” that began in the 2010s, it’s unsurprising that an alternate media universe would emerge to provide safe harbor for actual, alleged or purported transgressors — of social mores or politics or misbehavior — who would have been derided but maybe not disqualified in earlier generations.
By dint of his down-home edginess and comfort with slick filth, Von somewhat overlaps with the rest of the manosphere. What sets him apart is that he is not particularly cowed by fame or wisdom or authority or aggression. He blends curiosity with humility, and treats his guests as conveyors of mystical information, as if he’s always slightly punching above his weight.
Occasionally, Von’s guests say things to his face that scan as lightly dismissive. Criticizing Von for his Trump interview, the leftist streamer Hasan Piker told him, “You’re not going to hit him on stuff that he has no answer for.” But Von doesn’t take offense; instead, he concedes his shortcomings. “I thought that just because I had some political people on last year that I knew about politics,” he told Piker. “I do not. That was a trap.”
He knows what he doesn’t know, and thereby leaves room for chats with unexpected tributaries. His naïveté is both honest and strategic, a carefully laid roadblock protecting Von and forcing everyone else to move at his unlikely rhythm. Through humor, he asserts a quiet dominance over the chats. And sometimes, he’s the butt of the joke. In almost every episode, there comes a moment when Von’s guest stumps him. It’s never a gotcha, and the topic is rarely something terribly obscure. It could be as simple as an event or word or person that Von hasn’t encountered before. Some recent examples: Mitchell-Lama housing, the Kurds, who wrote the song “This Land Is Your Land,” misandry.
Other hosts might nod along or bluster their way through or be arrogantly dismissive. But Von does something quite different: He stops the conversation and asks for clarification. He’s keen to be the student. It’s a small gesture, but a meaningful and revealing one.
Even the way Von sits appears guileless — sometimes his hands gather in his lap shiftily, or he rubs his thighs for comfort, little fidgets that suggest unease. Much of the time, one foot rests at a 90-degree angle to the floor with the other foot atop it, like an idle middle schooler.
The pacing of Von’s conversations can be herky-jerky, as if both Von and his guests are tentatively exploring a new world together. Offscreen, a producer pulls up text and images from the internet for them to look at, and sometimes there’s a slight silence as they take in the information. (A rare exception was when Timothée Chalamet came on the show — his antic energy and active shilling for his role in the Bob Dylan biopic “A Complete Unknown” tugged Von out of his chill.)
Von, primarily, wants to sit back and have his mind blown; he almost never disagrees with his guests, though his access is beginning to activate some more definitive stances. Sanders, the senator from Vermont, treated his time with Von like a civics lesson, and Von was a deeply game student. America, Von groaned, is “a shell LLC for [expletive] big corporations.” He added, “Then what am I? I’m just an idiot. You almost feel ashamed of yourself,” he said, as Sanders agreed enthusiastically.
Von paid equally rapt attention to Laila Mickelwait, an anti-sex-trafficking activist who led a campaign urging PornHub to remove underage content, as he did to Wayne Owen, a former New York City sanitation worker, who brusquely recalled his smelliest stories and mused on ways one might dispose of a body undetected. (“What ethnicity probably has the worst smelling garbage?” Von wondered.)
He can sometimes free-fall into inventive left-field phrasing that achieves a sort of bliss. He said he once saw the boxer Evander Holyfield eating, putting French fries in his “Panamouth Canal.” Kissing someone with lip filler is “like trying to eat two shrimps that won’t give up.” Nudity is “the Lord’s matte finish.” When Sanders spoke about staying in a centuries-old home in Oxford, England, Von replied, “You got to bring your own plumbing, I’m sure.” You’ve never seen Sanders guffaw so deeply, one of three genuine belly laughs Von extracted from the normally unshakable curmudgeon.
While Von might socially caucus with other manosphere figures — they’re all regular presences at Ultimate Fighting Championship events and some of them sat together at Trump’s inauguration — his alignments aren’t terribly political, or even terribly masculinist, at least not by comparison. (That said, by my count, less than 20 percent of his guests in the past 12 months have been women.)
His politics, to the extent that he reveals them, don’t fall neatly along party lines. They reflect the choose-your-own-adventure political affiliations of huge swaths of Americans. Lest he be pigeonholed, Von airs political guests roughly back to back, to provide balance — Sanders and Trump last August, Owens and Piker last month.
Instead, he seems to be moved by an inner morality — an instinctual defense of the downtrodden. He returns frequently to the Israel-Hamas war, as he did in Owens’s episode. A clip of their conversation, with both Von and Owens criticizing Trump’s support of Israel, was circulated widely by left-leaning accounts, and painted as antisemitic by the right.
But occasionally his views tilt the other way. In February, he posted and deleted a message on X that was critical of President Volodymyr Zelensky after the Ukrainian leader’s calamitous Oval Office meeting: “Tell that guy to give us our tax dollars back.”
Morality doesn’t preclude humor, though, or offense. In Von’s calculation, they come from the same soil: an upbringing among the dispossessed. His fault lines don’t harden along lines of race or gender or sexual orientation or political affiliation. Instead, he asks, Are you getting stepped on? If not, you’re on the wrong side. It’s the clearest point of distinction between him and the rest of the manosphere.
That’s even more clear when Von leaves his podcast studio and heads out on the road to do stand-up. In early April, Von’s “Return of the Rat” tour went to the University of Mississippi, in Oxford.
“Lotta white people,” he deadpanned about the audience composition at the beginning of his hourlong set. “Thank you for coming to this very special meeting.” Awkward laughs. “I’m not racist, bruh. Unless you are. You first.”
On “This Past Weekend,” Von deploys affability to put others at ease; onstage, he uses the same to soften up crowds so as to leave them vulnerable to shock.
Face-to-face with his audience, Von — limber, mischievous, aware of his own silliness — toyed with the gap between who shows up and who he’s really addressing. Most of Von’s comedy is about have-nots, loving roasts of people who might be at varying valences of societal disadvantage: Black people, gay people, people with developmental disability. This is the racy and bawdy comedy of two or three decades ago, when identity politics was a luxury product, but delivered with warmth and affection, a dynamic that was often lost on Von’s roisterous crowd.
His politics, such as there were politics, were those of equal opportunity discomfort, the permission to insult equally — gay jokes that also triggered straight people’s discomfort with gay people; jokes about Black people that also toy with white racial anxiety. The laughter, when it came, was stilted and uncomfortable. Was Von with them or against them?
He had flickers of Bill Burr’s ethical common-man exasperation, and also the quicker-than-he-seems gumption of Larry the Cable Guy. In one segment, he glibly described Black-on-Black gun crime as “chocolate freeze tag” and bemoaned how violence can ensnare innocent bystanders. The solution, he said, was to teach young Black men to shoot in the same place as young white men: “In school!”
Referring to Oxford’s trapped-in-the-antebellum-South quaintness — the clock at the top of the town square courthouse “said 5 p.m.” He paused. “In 1862.” — Von joked that someone there jumped out from the bushes and asked him, “You got any news from the North?”
Von exulted, “You’re free, buddy!” Then he talked about ordering okra at a restaurant, calling the vegetable “slave jalapeños.”
These bits — the line-crossing race talk, the hot-button words, the naughty glee — were rude, and presumptuous, and like many offensive things predicated upon a fluency with life’s endless tragedies, also funny, or close to it. But Von delivers them without vitriol or judgment. His comfort is, depending on the audience member, an invitation to boorishness, a safe place for liberal friskiness, or a squeamish line too far. Von plays to them all, while poking at them, too.
He painted the younger version of himself as an aimless drug user, a person whose family all but dismissed him as a child. And he sprinkled raw childhood pain throughout his set. He described his mother’s reaction to his being placed with learning disabled schoolmates, booming, “‘Oh, you’re retarded? How much is that going to cost us?’” He wasn’t delving into damaged relationships with family to demean, he said: “I’m just trying to tell you how I ended up on drugs.”
Ultimately, the person he was the harshest on — or the most willing to sink teeth into — was himself. Stories about his upbringing turned Von into a fritzed-out Garrison Keillor. At the ice cream shop where he worked as a teen, “We were the Underground Railroad of autism,” he said. “You open up the freezer, Harriet Tub-ism would jump out that bitch.”
Those early letdowns “burned off a part of me that was hopeful.” But those mishaps and misadventures made him observant, tolerant and also ambitious. At the end of the set, he showed a trailer for a movie, written with and co-starring David Spade, that Von said would come out later this year though it had been rejected by countless studios. He spoke about feeling ostracized by Hollywood and not seen for who he is — the same sort of language he’d earlier used to describe his family, his friends, the people of his childhood.
Being the one onstage, he suggested, didn’t make him any different now. Von’s comedy — and increasingly, his political worldview — boils down to a crucial framework: You’re either one of them, or one of us. How far he goes, however, may hinge on making sure both sides continue to claim him as their own.
Jon Caramanica is a pop music critic who hosts “Popcast,” The Times’s music podcast.
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