TRUMPED

Andrew Schulz: The Comedy Podcaster Who Roasted Trump to His Face

Andrew Schulz lured Trump in with a false sense of security before embarrassing him in front of his core constituency of anti-woke young men.

The hustler never thinks they’ll be hustled. How else to explain Donald Trump blundering his way into his latest podcast interview with comedian Andrew Schulz?

Trump’s 90-minute sit-down on Andrew Schulz’s Flagrant with Akaash Singh podcast has clocked more than 2.8 million views on YouTube in less than 48 hours. It also provides a soundbite that Vice President Kamala Harris’ presidential campaign has already turned into a howler of an election ad.

The Harris-Walz campaign captured the moment Trump froze when Schulz asked the former president what happened to his VP, Mike Pence, before cutting to the rioters of Jan. 6, 2021, shouting “Hang Mike Pence!” As Schulz quipped, “He’s hanging out somewhere?”

They’ve also taken advantage of another moment where Schulz laughed in Trump’s face when he attempted to describe himself as “basically a truthful person.”

It’s a sharp contrast from Harris’ own interview choices this past week, where she sat down with one of the most popular podcasters in the world, Alex Cooper of Call Her Daddy, as well as the former self-proclaimed “King of All Media” Howard Stern, and in between, sat down for a live chat with the women from The View.

So how did Trump let a comedian make him look so foolish? Perhaps Trump’s own press team didn’t do their due diligence on Schulz, thinking he would prove just as amicable and easy to win over as the former president found comedian Theo Von, whose podcast This Past Weekend ranks not far below Call Her Daddy on Spotify’s listening charts.

But Schulz is in a different category from Theo Von, or Joe Rogan for that matter. Schulz is a hustler. He was that way when he got the attention of MTV and VH1 in the early 2010s, becoming a keystone not only of their Guy Code franchise, but also appearing as a host or panelist on multiple other programs. He was that way when I interviewed him for my podcast in 2015, back when Schulz co-starred on the little-seen IFC hockey sitcom, Benders.

It was Schulz’s hustle that got him to break through as a stand-up, putting out his new hour in a series of smaller segments on YouTube, which earned him the attention at Netflix for a multi-part special in 2020. And he was still that way earlier this year, when Schulz delivered a blistering performance near the end of Netflix’s live three-hour Roast of Tom Brady.

Trump and his handlers may have thought they were getting just another edgelord bro comedian who could and would play nice. But they didn’t get a fawning pawn in Schulz. They got a crowd work chessmaster. Or in a metaphor or cliche that the kids these days might prefer, Trump f---ed around and found out.

Schulz slow-rolled the former president, lulling Trump into a false sense of security by skirting pretty much anything resembling a policy question for the first 50 minutes or so of their conversation. Instead, he opened by asking Trump about his kids, how he felt about surviving an assassination attempt, and joking about Trump’s speaking style, which Trump claimed was more intentional “weaving” than absent minded rambling.

But after Trump signaled to his handler that he’d like to keep talking past the hour-mark, he began to let his guard down. And that’s where Schulz began treating Trump more like a front-row audience member than a former president.

It was all in the last 25 minutes where Schulz zinged Trump about where’s Pence now and where he laughed in Trump’s face when he claimed to be “basically a truthful person.” It was where he got Trump to crack by suggesting he’d want to keep abortion legal for the sake of his college-age son, Barron, where Schulz emphasized the need for IVF in allowing his wife to carry their first child, and finally where the comedian poked a massive hole in Trump’s campaign slogan.

“I would like my legacy to be the same as the term MAGA, Make America Great Again,” Trump said. “I’m going to make this country great again. It’s not a great country right now.”

At that, Schulz interjected to prove himself more patriotic than the former president. “It’s always a great country,” Schulz insisted, before offering up one piece of flattery: “I think that Donald Trump can only happen in America.”

Sean L. McCarthy is an entertainment journalist whose byline regularly appears in The New York Times, Decider and elsewhere. He hosts a long-running podcast interviewing funny people in the funny business, The Comic’s Comic Presents Last Things First.

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