Theo Von’s interview with Donald Trump makes more sense than you think

Even among a long list of bizarre Donald Trump moments, this clip was a head-turner: The former president asking his interviewer a series of questions about his cocaine use. “That’s down and dirty, isn’t it?” Trump asked Theo Von, who interviewed him on August 20 for his YouTube podcast, This Past Weekend.

The clip went viral almost immediately, not only because it’s rare to hear a presidential candidate so openly discussing drug usage, but because Trump, for once, seemed genuinely interested in a conversation that wasn’t about himself. It was also a strange “...who?” moment for those unfamiliar with Von, a mulleted stand-up comedian turned podcaster, in the style of Joe Rogan. Digital media has responded with a series of Theo Von explainers, attempting to convey what about the relatively unobtrusive comic may have caught Trump’s attention.

But in fact, there really isn’t that much to explain — at least not about Von himself. The shifts in internet culture that brought him his platform, though, are a bit more interesting.

Von — his full name is Theodor von Kurnatowski — is something of a one-size-fits-all commentator, one whose personal political beliefs seem anodyne enough to make him palatable to people across the political spectrum; he interviewed Sen. Bernie Sanders (I-VT) the week just prior. With Trump, Von stuck mainly to the personal (mutual friends from the world of UFC, Kid Rock’s brother’s golf swing, sobriety, how good the Trump boys are at hunting) before getting lightly political (they briefly discussed health care reform but mostly talked about how much they hate lobbyists). The interview’s big viral conversation about cocaine came when Von tried in vain to get Trump to talk policy regarding the opioid epidemic. The subsequent chat about doing drugs was Trump redirecting the subject, but it was much more aligned with Von’s typical podcast conversations, which normally veer away from more incendiary subjects and toward topics like wrangling drunk mall Santas.

A veteran of the same early-2000s reality TV industry that former Fear Factor host Rogan once thrived in, Von first made his mark as a young contestant on MTV’s reality travel competition show Road Rules. He later gained acclaim on comic competition shows like Last Comic Standing and Reality Bites Back, holding his own against other comedians like Amy Schumer and Tiffany Haddish. In the early era of comedians turning into podcasters and vloggers, Von became popular as a guest on other standups’ shows, all while his own show, launched in 2016, took off and grew to its current audience of nearly 3 million subscribers.

The interview, which the pair alluded to having been orchestrated by UFC CEO Dana White, was apparently part of a recent series of drop-ins to UFC-adjacent podcasters, including Von, Adin Ross, and Logan Paul. Yet there’s a lot more at play here than Trump appealing to wrestling fandom. In his newsletter, writer Max Read coined the term “dipshit outreach” to describe the kind of everyman tour Trump and his running mate Sen. JD Vance have embarked on. Read’s thesis is that Von, along with the other podcasts, vlogs, and livestreams that Trump has appeared on, attract a specific type of Trump-loving demographic. As he puts it, these are “guys who like ‘edgy,’ trollish, hedonistic, attention-seeking personalities.”

Von has skillfully branded himself as a relatable, down-to-earth type, a Southern boy originally from what he’s described as the rural, poor side of Covington, Louisiana. He comes across as more interested in people than in their politics, so we might think of Von as more or less on the wholesome end of the troll-magnet spectrum. That may well be true compared to the other men on Trump’s roster, but he has had his moments.

Most notably, his 2015 appearance on Bertcast with Bert Kreischer includes an extended segment in which Von repeatedly drops the n-word — hard ‘r.’ Von couches his use in an anecdote in which he claims that Black kids in his neighborhood were the ones ironically using the word, which he’s just conveying to his audience. He then proceeds, with Kreischer, to spend several minutes expounding upon why his use of the n-word in this context is fine, actually. That’s not the only time he and Kreischer defended the indefensible; last year, he joined Kreischer’s show Two Bears, One Cave to do the same sort of performative justification — this time for white men doing blackface.

While difficult to listen to, these conversations sum up what might set Von slightly apart from some of his colleagues in comedy — he doesn’t think just anyone should be able to say the n-word because of free speech; he thinks he personally gets to say it, because he somehow earned it. As for blackface, he doesn’t think it should “count” when it’s donned by someone who’s marginalized in a different way, because that person also somehow earned it. This is, in America, a whole type of guy.

This is exactly the kind of content Von’s demographic loves and the kind of contrarianism Trump himself delights in and gravitates toward. Though most of Von’s more recent content is inoffensive, it’s not insignificant that his popularity was built on this kind of vibe.

Von is older than both Ross and Paul, who carry a more direct appeal to Gen Z. But Von’s own persona, while less brash and irony-tinged, has its own broad allure; much like country mega-star Morgan Wallen, he’s frequently self-effacing and self-deprecating, both as a way of performing relatability and as a way of preempting any moral objections to his tone. Like Wallen, he’s already confessed to being an imperfect narrator and commentator, so how can you hate him for it?

His stand-up comedy weaponizes this strategy as well. At one point during a 2012 Comedy Central special, he pauses mid-sentence to admonish people who are laughing at the “wrong” part of a joke about Black people. “That’s not the joke, people that are laughing, that’s racism,” he says, in the middle of a string of jokes full of racist assumptions. The admonishment functions as both a deflection and a defense.

Of course, many comedians believe the cause of comedy itself makes it an unimpeachable high ground that justifies the performance of outlandish and offensive material, and likewise lament the rise of fabled “woke scolds” who criticize comedy that targets the vulnerable and the marginalized. Unlike other similar comics — Shane Gillis comes to mind — who’ve doubled down on their offensive material in recent years, Von tends to avoid falling back on this rhetoric and mostly seems to avoid the conversation altogether. He’s interested in pushing the buttons, but he’s not so interested in pointing to the consequences he might face for pushing them. Much like Rogan, while he aligns with Trump on vibes, and his jokes frequently give trolls and racists permission to laugh for all the wrong reasons, his own politics seem far more middle-of-the-road. In comedy, that effectively makes him a moderate.

Trump’s appearance on Von’s show, then, just a week after Sanders, says something about the breadth and potential of these so-called dipshits in his audience. That two major figures from either side of the political spectrum chose to appear on a former Road Rules-er’s video podcast is a shockingly in-kind outcome for a modern internet culture that turns comedians into influencers and podcasters into pundits. Who will ultimately win their hearts — and votes — remains the question.