A comedian who delivers jokes with moral clarity and a sharp tongue

Washington Post

11-02-2025

Next in Arts & Entertainment A comedian who delivers jokes with moral clarity and a sharp tongue
By Ashley Fetters Maloy
February 11, 2025 at 6:00 a.m. EST
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There's a joke Caleb Hearon likes to tell about trans people — and if that sounds like an alarming way to begin, keep reading.
It's an observational bit about an aesthetic difference between trans men and trans women. 'Trans guys always pick something proper. They'll be like, 'I'm Elliott.' 'I'm Liam.' 'I'm E.J.'' Hearon says. Trans women, he says, just go for it, calling themselves unprintable anatomical slang terms before phantasmagorical titles like 'Goddess Amethyst of the Rainforest.'
Nobody loves this joke more than the transgender fans at his shows, Hearon says, over lunch on a sunny autumn afternoon in Brooklyn. The actor and (cheekily self-described) 'beloved gay comedian' has been headlining packed comedy venues, prompting howls of laughter with subversive punch lines like, 'Being bisexual is the new being Italian — a lot of wearing leather jackets and pretending to be discriminated against.' For years, better-known figures in comedy have struggled to make relevant, topical, good jokes about the so-called 'issues' of sexuality and gender identity. Many wind up either offending audiences or just failing to make them laugh. Hearon, though, sidesteps both of those common pitfalls, and he makes it look easy.
Hearon, a 30-year-old native of Brookfield, Missouri, performed two dozen shows across the United States in 2024 and launched a weekly talk-show podcast titled 'So True.' (Its tagline, in Hearon's signature faux-affectatious young person's syntax: 'Basically just getting into it and sorting it all out and kind of identifying what's really real.') Hearon also headlined the 2024 'Netflix Is a Joke' festival and appeared in supporting roles in the recent comedies 'I Used to Be Funny,' starring Rachel Sennott, and 'Sweethearts,' starring Kiernan Shipka and Nico Hiraga. He begins a U.S. tour later this month.
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Hearon's most remarkable achievement, however, may be his constant illustrations of how deftly a gifted comedian can navigate changing social mores. While comedy elder statesmen like Dave Chappelle and Jerry Seinfeld have in the past claimed audiences are just too sensitive nowadays, Hearon's burgeoning career is proof that comedy can have a moral compass — and still be funny.
Hearon's initial plan was to be a lawyer. But while studying sociopolitical communication at Missouri State University and working in the Kansas City office of Sen. Claire McCaskill (D), he discovered improv comedy. After graduation in 2017, Hearon moved to Chicago and started a comedy career instead.
'I was like, 'I think I'm going to try comedy, and I'll give it my 20s,'' he remembers. 'And if I never make a dime and I end up, like, tucking my tail between my legs and going to law school in my 30s, at least for the rest of my life I can tell my kids and my friends and everyone that I spent my 20s being weird in Chicago with a bunch of cool people.' In the meantime, Hearon also worked at a nonprofit helping teachers in low-income districts to integrate social justice and service learning into their curriculums.
Caleb Hearon performs at South by Southwest in Austin in 2023. ()
After three years on Chicago's comedy scene, Hearon abruptly became internet famous during the coronavirus pandemic in 2020 when viewers discovered short front-facing videos he had previously released on Twitter. The videos portrayed Hearon having one side of a conversation, inviting viewers into a variety of plausible but amusingly weird situations. 'POV: You're a close friend venting to me about a situation where you were entirely in the wrong.' 'POV: You're my co-worker and I'm telling you the first part of an entire weekend I spent with our other co-worker.'
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Joel Kim Booster, an actor and comedian as well as Hearon's castmate in 'Sweethearts,' first encountered Hearon's work around that time. 'This was early days for this kind of comedy video. I really do think he was at the forefront there. And I, like most people, was obsessed,' Booster says. 'I was always like, 'How do you do that? Be funny like that, just standing waiting for the Brown Line [train in Chicago]?''
Comedy without malice
Despite his sweet-natured demeanor, Hearon is by no means a clean comic. 'I think a lot of clean comics are serial killers,' Hearon says with a laugh. 'There's something very malevolent about someone who — in this time in the world, when things are incredibly turbulent and incredibly bad for a large percentage of people — would go onstage with a microphone and hold hundreds if not thousands of people captive for an hour and be able to just be like, 'Isn't it crazy when you get the wrong milk at the coffee shop?' That is nuts.'
Hearon with 'Sweethearts' co-stars Nico Hiraga, left, and Kiernan Shipka at the SCAD Savannah Film Festival in 2024. ()
But there's a disarming friendliness, a distinct absence of malice, present even in Hearon's edgier material — and Hearon thinks a lot about how to maintain that tone. 'I do think the first and most important thing onstage is to be funny,' Hearon says. 'Then really after that, it's just like, 'Is it true to me? Is it loving?'' Hearon believes the joke about transgender people's chosen names, for example, works because it's an earnest observation made with familiar affection, not disgust or confusion.
'I have a lot of trans people in my life that I adore,' he says. 'I make jokes about trans people, I make jokes about being fat, … I make jokes about all the things [other comedians who've gotten backlash] want to make jokes about. They just don't come from a place of hating those people, and they're not mean-spirited or lazy.'
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'So I think it's possible to be all of it,' Hearon adds — empathetic and funny, sharp and respectful. Hearon has little patience for those who argue that being a comedian requires a lack of concern for others' feelings: 'I think you just don't give a f--- about anybody.'
Hearon, who was an organizer with Black Lives Matter in college and lately has been organizing with the Missouri affordable-housing nonprofit KC Tenants union, also spends a lot of time thinking about how to 'punch up' effectively. 'If I'm going to be hateful onstage,' he says, 'I want to make sure the hate is directed at powerful people with bad ideas.'
Certainly, the inclusivity present in both Hearon's work and his attitude have resonated with both his contemporaries and his audiences. When Hearon filmed 'Sweethearts' in 2022, 'it really did feel like he was king of the set,' Booster says. 'He knew everyone's name and story.' And more than once during his interview with The Washington Post, fans passing by pulled over to briefly, politely thank him for his work ('Hell yeah, brother. Thank you. That's so sweet,' Hearon responds) and acquaintances who've met him at other events stopped to say hello, delighted.
On that November afternoon in New York, Hearon was a few months shy of his 30th birthday — with no plans for law school in sight.