Stream It Or Skip It?

First he finishes ahead of Mr. Beast on Rolling Stone’s list of today’s top influencers, and now Caleb Hearon has accomplished something else the YouTube giant has not — his first stand-up comedy special on HBO.

The Gist: How did Caleb Hearon rank so highly with Rolling Stone, anyhow?

Although Hearon has become increasingly booked and busy in recent years as either comedic or emotional relief in supporting roles (he’s currently filming The Devil Wears Prada 2) on both the big screen (Sweethearts, I Used To Be Funny) and streaming (Overcompensating, Mr. and Mrs. Smith), his influence has spread most widely through viral clips from his podcast, So True with Caleb Hearon, hitting your feeds on TikTok and Instagram.

For his debut stand-up special, filmed in Chicago, the Kansas City comedian and actor fills us in on how he’s feeling “Midwestern aunt-pilled” as he enters his 30s, and how he balances his whimsical yearnings with a hostile world.

What Comedy Specials Will It Remind You Of?: Not many come to mind, but if you really stretch, you could maybe see Hearon as the “good cop” in a good-cop, bad-cop comedy duo with someone like Guy Branum.

Memorable Jokes: Hearon starts out by introducing you to his particular point of view, establishing that he knows it feels weird to feel good and happy having just turned 30. “There’s something about, the world’s on fire, but I’m like, let’s get silly with it, you know,” he says.

In describing himself as “stage four” in becoming a Midwestern auntie, he jokes: “I’m turning into a woman named Brenda who works in accounts receivable… like I’ll help you find a pair of pants at Lane Bryant.” He’s the type who might tear up watching a woman play catch with her dog, and also the type to visit antique malls by himself.

Which, he’s keenly aware, opens himself up to critics, even if most of them cannot get past his superficial looks. “I get cooked online by people who frankly should not even be in the kitchen,” he quips. “I used to get so bent out of shape about it, mostly because when they cook me online, they’re always going straight for fat… I’m bored. Like whatever. Do your research and say something actually hurtful to me.” Don’t worry. He gives examples. Including attempts by his fans to defend him online that hurt more than help, which is where he found the title of his HBO special when one of his fans stuck up for Hearon by proclaiming: “He’s a comedian, not a model.”

We learn that teenage Caleb was a bit of a stiff, really intense at student council meetings, asking his single mother for a business suit even though he had no business to attend to and his mom couldn’t afford it.

And through his one bit of crowd work, he offers his own suggested comeback for teens worried about other kids or adults calling them fat.

The second half of the hour digs into his insecurities as a young man growing up “gay in a red state,” how his mentally ill father may not have been the best dad but still offered his own brand of “redneck progressivism” until he died, and how he mourned their relationship afterward. Hearon wishes the political left had better ideas for supporting the trans community, but really goes after conservatives for what he sees as hilariously hypocritical attitudes. He also shares a story about going on a trip to Germany with his LGBTQ+ friends, only to find subversively dark humor in their visit to, as he puts it, “Holocaust.”

Our Take: Part of what makes Hearon so endearing in his podcast clips is how matter-of-factly he responds to the issues of the day.

As he confesses in the special after describing how emotional he got watching the woman in the park with her dog, it’s the little things. “That’s what it’s all about…and I meant it,” he says sincerely, adding: “That’s who I am now. I can’t stop taking stock of all life’s little joys and pleasures.” And what is so wrong about that? He even acknowledges that not everyone feels the same way, offering up as an example the gruff driver who gave Hearon guff after he referred to his friend in the back seat as “precious cargo.”

One way he stays in the good graces of these harder-edged, less-whimsical members of America is by referring to them as “brother” and “dog.”

For all of his talk about whimsy and simple pleasures, Hearon delves into dark topics such as his “Holocaust” trip or his youthful suicidal ideation. He gets such a kick out of hearing audience members say “Jesus Christ” at his specificity that he refers to their gasps as his personal Mark Twain Prize.

And then there’s how he talks about the America’s far-right politically, which in September 2025 comes across more stridently profane than most actual Democrats these days by slinging gay slurs toward many of the more vocally conservative Republicans.

“My favorite straight guys out right now are conservative Republicans. I don’t care. I love them,” he said.

“I love ‘em. I think they’re so funny because they all say they hate gay people so much and they’re such f—-ts, you know what I mean? There’s an air of f—-try with these guys, like Ben Shapiro. That f—ing f—-t. I just. All these guys are like, ‘I’m worried about our men and boys.’ I will put you in Tupperware and put you away. Like, why are you so small and faggish? Jordan Peterson. That f—ing fruitcake.”

“Why are you wearing a bespoke little bow tie? I don’t — you’re trying to make some big pitch about manliness and you look like f—ing Pee-wee Herman, dog. I just want to put these guys in a locker. JD Vance, that f—ing f—-t. Have you ever seen a man need that much mascara to look compelling? Not even handsome, just compelling. God, watching him crawl around on his knees for daddy is so humiliating. The way that f—-t debases himself for Trump is so fucking humiliating. Or Ron DeSantis, that f—-t. I just. I almost feel bad for Ron DeSantis ‘cause he didn’t get the fun gay personality like Trump. He just got the voice. And I feel bad for him because Ron DeSantis wants to be the GOP’s guy so bad, but all of his press conferences are like, ‘Hello…..” “It’s like, OK, diva. I’ve heard that voice do Cher at Hamburger Mary’s Maryoke.”

In places such as Kansas City, Hearon almost feels nostalgic for “old-school homophobes” because they at least looked and acted the part, living as ranchers with lots of kids; compared to these haters, of whom he dismisses: “Now they’re Yale grads wearing Brooks Brothers. I can’t even respect you.“

So no, Hearon doesn’t want to debate “these losers about trans people,” claiming they don’t actually know any trans people or even care to.“The reality is, they just want to make more money for their billionaire friends and this is what’s working right now. And that’s the really sad part. They’re not going to do anything for us.”

It might not be funny, but it’s not a funny situation for Hearon, or the LGBTQ+ community, or those that love them, or their friends, or their neighbors, or their co-workers. So really, it’s not funny for any of us. It never was.

Our Call: STREAM IT. So yeah, it’s quite a balancing act, what with the whimsy up top and the seriously dark rebuttals to his haters as a finisher. But we’re living in dark times, and it’s important to hear from the people we’re trying to bully into submission that while it’s not all fun and games, even those we’re bullying can still see the light and the whimsy through the darkness, and still manage to spread that light and whimsy as much as they can.

Sean L. McCarthy works the comedy beat. He also podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.