Why Trump Was on Andrew Schulz’s Flagrant Podcast

On October 9, just days after Kamala Harris’s media blitz — which included appearances on 60 Minutes, Call Her Daddy, The View, The Howard Stern Show, and The Late Show With Stephen Colbert — Donald Trump was a guest on Flagrant, a comedy podcast hosted by stand-up Andrew Schulz, Akaash Singh, AlexxMedia, and Mark Gagnon. Liberals online laughed at the contrast. One tweet read, “Imagine voting for a guy who won’t sit down with 60 minutes but will sit down with Andrew Schulz 😂.” But the audience of Flagrant and its cohort of male-dominated podcasts should not be so casually mocked. With his Flagrant appearance and August guest spot on the even more popular This Past Weekend With Theo Von, Trump has raked in more than 14 million views combined so far (for comparison, Harris’s Call Her Daddy clip on YouTube has yet to hit 1 million); it’s clear that Trump sees this comedy sphere as central to his attempt to, as the New York Times wrote, “court the Manoverse.”

Von and Schulz are two of the biggest stars of the world of independently branded bro-comedy podcasts in the vein of Joe Rogan, along with names like Shane Gillis, Tim Dillon, and Legion of Skanks. Regardless of Netflix’s significant embrace of these comedians, they all position themselves as outside the mainstream due to their resistance to political correctness, contrarian takes on liberal conventional wisdom, and “both sides are corrupt” nihilism. While the comedians of this world all appear on one another’s shows, their podcasts range in how they approach that sensibility. Flagrant is more of a hangout podcast, where conversations about politics are a jumping-off point for easy jokes. Schulz is obsequious, either chummily laughing along to whatever is being said or clearly waiting for his turn to talk. In contrast, Von listens. Unbelievably naïve and undeniably charming, Von asks simple, basic questions and, unlike Schulz, seems genuinely curious about his guests’ answers. But his guilelessness does lead to him being open to conspiracy theories and lazy stereotypes. As Von’s show has grown more popular — it has 3.2 million subscribers on YouTube and is the fifth-most-popular comedy podcast on Apple Podcasts — he has deliberately booked guests he feels can inform his audience of what’s going on in the news. Still, while they differ stylistically, both Schulz and Von’s shows have found massive success. Over the past six years, both comedians graduated from performing in clubs to theaters to arenas, thanks to their appeal to massive audiences of largely disaffected young men.

The politics of these comedians can be hard to pin down since they tend to reject both political parties and support both socialist and libertarian policy ideals. The liberal media has ignored or dismissed these shows as right wing and, in turn, the right-wing media have claimed these shows and this spirit of comedy. (Ben Shapiro and Tucker Carlson both made documentaries celebrating these comedians as warriors defending comedy under attack from cancel culture and/or “wokeness.”) Trump’s targeting these podcasts in the final months of his campaign is arguably the final step in these shows embracing and being embraced by the Trump movement. “When we talk about right-wing comedy, people will ask, ‘Are they really right wing?’” says communications professor Matt Sienkiewicz. “And we say, ‘We don’t mean their politics necessarily, but they’re tying into a right-wing media sphere.’ But with this podcast tour, Trump was trying to include them in his brand, and these people are accepting that branding.”

Sienkiewicz has been studying this thread of comedy for years with his colleague and fellow professor Nick Marx. In 2022, they published the first book on the subject, That’s Not Funny: How the Right Makes Comedy Work for Them. In the book, they describe a new right-wing media ecosystem that includes Fox News, online conservatives like Shapiro, right-wing extremists, and ostensibly independent podcasts like The Joe Rogan Experience. “The ways in which people discover new comedy today — algorithmic suggestions on YouTube, retweets on Twitter, cross-promotion on podcasts,” they write, “provide a set of pathways that connect more banal right-wing humor to the truly evil stuff, up to and including actual neo-Nazi comedy spaces.” While the left may dismiss this comedy as not funny or irrelevant, Sienkiewicz and Marx argue, the large audiences these shows have built mean they must be taken seriously. After the Flagrant episode was released, we talked to the professors to get a better sense of why Trump made these moves — and why they might work.

What does it mean to you that Trump has appeared on these podcasts?
Matt Sienkiewicz: It is the total victory of this avenue of media over legacy media. The book we wrote said we were approaching parity — that these networks of podcasts that trade guests and promote one another were getting toward having the critical mass that would be the equivalent of the late-night shows. That’s where we’re at now, basically: You have comparable audience sizes, you have better audience targeting, and it’s very clear that the Trump campaign has decided this certain set of youngish men is where it’s going to make its gains.

Nick Marx: Young men are a deficiency of the Harris campaign and a strength of Trump. He’s hammering that strength. What’s changed in the past two years is that you’ve seen the door that’s been opened by comedy lead to this bigger growing entertainment complex. And it’s not just limited to comedians. Figures like UFC CEO Dana White loom so large as this connector among Theo and Rogan and Schulz and all these others. Trump can speak the language of this type of comedian who’s also aspirational in moving beyond comedy and being a sort of mini entertainment mogul.

These hosts often refer to themselves as moderate or independent. When Bernie Sanders was on Theo’s show the week before Trump appeared in August, Theo said his dream ticket would be Bernie and Trump running together. How do you reconcile this?
M.S.: Bernie and Trump are also the dream ticket of Blue Chew, a product geared toward a certain kind of man. It is a demographic play. It’s a way to court a certain audience, and Rogan’s been doing this for a long time. Rogan was a Bernie guy in 2020 and then when that ended he became a Trump guy. The best explanation is just this is the next best guy to go to to appeal to the audience that buys the off-brand Viagra and meat boxes they are trying to sell on these programs.

N.M.: I just read it as being attracted to anti-Establishment figures, first and foremost. The smart-perspective voters of either Bernie or Trump can follow their respective paths, but the initial attraction is very strong to people who feel alienated by whatever perceived mainstream that the two parties represent. I get that you come to see very quickly what the differences are between their two ideologies, but the initial impression of anti-Establishmentarianism is a pretty easy draw.

What did you think of the interviews themselves?
N.M.: What stood out is both Flagrant and Theo led off with questions about Trump’s sons and role as a father. I can’t help but read that as sort of an alienated-young-male demographic that tends to flock to those shows searching for some kind of strong paternalistic daddy figure. So you have Donald Trump having to grit his teeth while complimenting his elder adult sons, whom he clearly doesn’t love — he compliments Don Jr.’s hunting abilities at one point — but his campaign and the interviewers understood that Trump talking up his strong fatherly role was good for both of them.

M.S.: Schulz turning Barron into a character — joking about how Barron’s gonna get laid in college — was actually a very effective way comedically to moderate Trump’s abortion position for the Blue Chew demographic.

One thing that jumped out was how much the Flagrant hosts laughed, both with and arguably at Trump.
M.S.: They want to say that Trump is funny. That does not mean that he is crafting jokes, but they like how he shoots from the hip. One of the guys begs him to shoot a little bit less from the hip, essentially begging for moderation, but they want to give the impression of a very loose, open-ended, anything-can-happen conversation.

N.M.: I made the connection between what those shows were doing and what Gutfeld! successfully did. They’re less invested in the specific policy points and plans — what little there is of those — and more interested in the reaction and the discourse that his appearance will generate and sort of riffing about that. You see Andrew and Akaash saying the kind of points that they know will get circulated online, and they punch those up with big laughs.

M.S.: Did you watch Trump’s Gutfeld! appearance? Gutfeld’s a professional comedian, in that he’s got jokes you would expect in a late-night show. They were talking about the assassination attempt on the golf course, and he asked Trump if he could have taken him out with his three wood. That’s a Johnny Carson joke. These guys are not doing that so much. Theo Von is definitely not doing that. But by making him seem like less of a threat, it makes him seem more moderate.

As people who have studied these kinds of comedy podcasts, what were the moments that felt most typical for the shows? 
M.S.: It’s these moments on Flagrant where, for no real reason, somebody says something that has to do with bad driving and then somebody’s like, “It was probably my wife driving.” Just a stupid misogynist joke tossed in there to say, “Hey, we’re just boys hanging out!” Those are the moments that tie politics into this thing.

How would you differentiate Theo Von from the Flagrant guys, both in general and how they approached Trump?
M.S.: Von is one of the most remarkable performers that I’ve seen, insofar as he truly portrays himself as knowing nothing. Literally nothing. There’s one time where he asserts a fact about health care and then after, he says, “I don’t even think I’m lying.” But that’s his thing. My favorite moment from that one, comedy wise, was when Trump goes off on this riff on Jake Tapper and Von just looks at him and says, “I saw him at a Whole Foods once.” And then Trump says, “Yeah?” It’s like this bizarro anti-comedy.

But also, when he’s sitting there talking to Donald Trump about cocaine and the difficulties of his substance abuse, it seems much less artificial. It doesn’t seem like he’s reaching for the joke about the bad woman driver. He’s not reaching for some edgy joke about Barron getting women pregnant. He is reactive, and he is willing to go in a funny direction that isn’t a crafted joke, which also leads to moments of sincerity. It’s really interesting hearing Trump talking about how his brother Fred’s alcoholism resulted in him never drinking, for example. Flagrant is much more planned out and charted and strategic to me, and there is an awareness of We’ve got to get a joke in every six minutes.

N.M.: Von is interesting in contrast to someone like Rogan, who often seems to be waiting to make his point and be like, “Have you seen this cool article?” I was struck by how much Von just kind of listens and then is like, “Wait, what’s a third party?” — the sort of childlike questions you might have about politics that I assume mirror the mind-set of his listenership.

N.M.: It’s probably a simple point, but it’s one worth reiterating: It’s no accident that Harris is on the more shortform, sound-bitey platforms, like Colbert and 60 Minutes. And these podcasts are the longform, rambling, hour-and-a-half episodes. Rogan episodes push into the four-hour territory. We take that for granted now because it’s been around for ten years, but that was a pretty big innovation. That’s firmly branded podcasting as this alternative, freeform space that’s a little bit more amenable to right-leaning politics and grievances and diatribes. And for their male audience, it also plays into the grievances with identity-driven politics today. If there’s a perception that mainstream media is overly catering to historically minoritized populations, then men need to create their own space.

Theo Von said he would love to have Kamala Harris on. Do you think she should do it?
M.S.: Let’s say yes.

N.M.: Yeah, me too.

M.S.: He’s a remarkable know-nothing, but he’s a fair voice in that sense. He did not, unlike Flagrant, reach for these low-hanging-fruit jokes. If she thinks she can do a good job, she should do it. I’m not willing to say I trust knowing how she would perform, but going on there and doing a good job would be very valuable, whereas going on Flagrant and doing a good job would not be.

N.M.: Tim Walz should go on Theo Von! What happened to the sort of Menards dad persona that they got such a big bounce off of when they announced that ticket a month or two ago? Why is he not out there showing how Midwestern and funny he is? To take nothing away from Harris, I don’t know why we put him on a leash and why he’s not out there pounding the pavement with these very likable, have-a-beer-with-me, let-me-talk-about-your-gutters types of things. I understand on the one hand wanting to control and minimize Harris’s weaknesses, especially on specifics and whatever else she’s accused of. But Walz is such a likable person that he seems like a natural fit, especially for Von’s show.

In your book, you describe this cohort as “the legions of libertarian podcasters.” How have you seen the politics of this group evolve into where Theo and Schulz are now?
M.S.: Schulz is drafting off of the sensibility of the libertarian gang, but at a remove. The more intentional parts of this movement — Dave Smith, the Skanks, et al. — try to really closely connect offensive speech with the virtue of free speech. In the Trump interview, Schulz has a touch of this when he talks about America as a place that gives you the freedom to be your best self (and Trump just refuses to stop saying America sucks). But honestly, I see Schulz as so much more strategic and scripted, at least in the Trump episode, where the little offensive digs seem like window dressing to avoid making the episode seem like a pure political ad.

Von … is just so committed to not having an affirmative set of information and beliefs. He ties in a little through his “I’ll ask anyone anything” ethic. However, even just by being critical of things like drug use, he creates a fundamentally different sensibility.

In your book, you argue that what got these podcasts associated with the right is whom they give platforms to, which at the time was done under the guise of free speech. How does that lead to Trump?
M.S.: There has been a sort of testing with Rogan putting on voices that are a little bit different. He’s definitely found voices that are hard to place politically, and some that are less hard to place but from across a spectrum. But over time, you’ll see a trend of more and more of these right-wing voices being the people he chooses to give the outside perspective. That is A/B testing of what plays better. It also has to do with perceptions of the mainstream media. As more and more people understand mainstream journalism as being affiliated with the Democratic Party, even if these podcasts are doing something with the Republican Party, they can still act like they’re being countercultural. Even if you’re talking to a presidential candidate.

Do you think these appearances could have an impact politically?
M.S.: The traditional way of getting messages out and driving people to vote doesn’t seem to be working. That doesn’t mean that this one will, but it’s different. It’s clear the idea is these are the people who don’t vote but, if they voted, would vote for you. The targeting of podcasting is perfectly geared for this. So if we end up in what we’ve had over and over again, where we’re literally talking about thousands of people in three states, it’s completely plausible that being this targeted will help. These guys don’t vote, but if they get 80 percent of them …

N.M.: That’s the targeted nature of podcasting. Focusing on a population of young people who either have never voted or have been turned off by previous elections, in my very amateur opinion, is Trump’s path to victory. And that’s what comedy does. Whoever wins the battle for people who haven’t voted, who are disinclined to vote, with this very narrowly targeted strategy, I think is going to emerge a winner.

What do you think of the liberals who were on Twitter dunking on these appearances?
M.S.: They don’t understand that the things that they take seriously and think are impactful are not nearly so impactful and prominent as they believe them to be. Harris on Colbert is very comparable to Theo Von. I wouldn’t know how to suss out viewers versus active viewers versus engaged viewers, but they are close enough. These podcasts feel low grade, they feel minor league, but we’re in a world where all media is increasingly minor league. Also, when it comes to comedy criticism, go watch a whole episode of Colbert. There’s hits and misses. But the Theo Von thing, with its few funny moments, is also very comparable to watching an hour of okay television. So part of it is just not realizing that what they’re looking at is not so different from the things they take seriously.

N.M.: I want to reiterate the bigger point of our book: that this is comedy, even if you might not like it. I just am concerned about the galvanizing effect of shows like these on that specific demographic, which is much more homogeneous than the comedy audience for left-leaning comedy. The Democratic coalition is much more diverse and heterogeneous, and you’ve got all these different identity categories that you have to play to and make sure you’re making laugh and not offending. I fear — and I have no evidence for this — there might be a diffusing effect that makes comedy for liberals not be as powerful as it is with the laser beam-focus of right-leaning comedy on this very specific group of independent-minded young men who may be voting for the first time.

M.S.: The community-building capacity of it does seem to be inherently stronger, and that might be something that is missed if you’re not part of that community.