This story was originally published on May 1, 2025. We’re recirculating it today, now that all eight episodes of Benito Skinner’s series Overcompensating are available to stream on Prime Video.
For Benito Skinner, there is comedy everywhere — you just have to know where to look. On a spring evening at a Bushwick wine bar with exposed brick and prices high enough to let you know the distressed décor is intentional, the 31-year-old comedian could have found enough material for a multipart character arc.
“Artichokes and Diet Cokes?” Skinner quizzes, slapping a leather-bound menu shut. “That’s fabulous. That’s us.” It’s a “very L.A.” order he adds, unzipping his cropped Tab Hunter–esque jacket and apologizing for his post-photo-shoot, “full beat” face with a raised eyebrow that tells you he is anything but sorry. Yet even the most perfect orders can falter, and we soon discover that this place doesn’t serve soda. We bravely decide on sparkling water. Would we like oysters, too? Skinner would, but I would not, and it turns out that he would not if I would not. There is a brief back-and-forth. The server glazes over and walks away. It’s a minor moment of awkwardness, but something about the situation gets the gears turning in Skinner’s head. “I loved that,” he declares, leaning toward me breathlessly. “That’s a monologue.”
On Instagram, where he’s known as BennyDrama7, Skinner puts the self-inflicted indignities of contemporary life through a megaphone. In his sketches, which became a sensation during COVID, he creates over-the-top, often deranged caricatures of famous and local-famous personalities: a delulu twink with face tape; a chronically oversharing hairstylist; Lana Del Rey gazing at cacti. He is particularly skilled at zeroing in on micro-humiliations, like pumping gas in your Chromatica Ball look or, like, dating a 36-year-old with a podcast, escalating mildly uncomfortable scenarios to eldritch horror. The skits are loud and brash, making Skinner the pickleback of comedy: crave-worthy to some, off-putting to others, but pretty good if you just roll with it and take the fucking shot.
Skinner lives in L.A., but today he’s in town for a promotional blitz for a new TV series on which he puts aside the drag getups he’s typically known for and draws on experiences that hit uncomfortably close to home. In Overcompensating, the ribald and seamlessly bingeable half-hour sitcom he created, produced, and stars in, the comedian plays a younger version of himself: Benny, a squeaky-clean high-school valedictorian arriving for his freshman year at an East Coast college campus, where students are railing coke in the library, having sex for clout, and undertaking hazing rituals designed to make them puke. With backing from A24 and Jonah Hill’s Strong Baby Productions, the show is due on Amazon Prime Video on May 15, and Skinner is counting down the days. “I need it out,” he says. “There’ve been so many challenges — beautiful challenges — along the way. Once it’s on the platform, I’ll sleep better at night.”
When Skinner was a student at Georgetown, the inspiration for the sun-dappled campus of Overcompensating’s Yates University, he wasn’t out yet. Benny, similarly, is in the closet, at first awkwardly attempting to date fellow freshman Carmen (Wally Baram), until they settle on rubber stamping their friendship with video-game marathons of Slut Slayer: Berlin, as well as having the ultimate bonding experience of simultaneously emptying the contents of their stomachs as Charli XCX performs. With a winning ensemble that includes The White Lotus’s Adam DiMarco, Black Mirror’s Mary Beth Barone, and Ms. Marvel’s Rish Shah, the series is lewd and brash, and no one — including flamboyant twinks, frat bros measuring their wizard’s staffs, or a suburban mom who names her rescue puppies after Maroon 5 songs — gets a pass from being lovingly torn to shreds. Along for the ride are more than a few details probably best not to think about too closely, such as why most of these college students are played by 30-something actors with bodies by Equinox.
At the same time, Overcompensating is a deft showcase for Skinner’s sharp writing. The droll delivery of lines like, “She’s like hanging out with a funeral,” could make you spit out your cold brew. In person, he has a quicker-than-Capcut wit and the kind of charisma that could make ancients cross plains to witness his town-square proclamations. He radiates the kind of warmth that makes you want to be part of his gang. And many do: Skinner is an informal member of Charli XCX’s brat squad; his boyfriend, Terrence O’Connor, helped bring brat summer to life, and Charli contributed original music to the series. There are scene-stealing cameos from Bowen Yang, Matt Rogers, Kaia Gerber, and James Van Der Beek. Kyle MacLachlan and Connie Britton play Benny’s parents. A Jennifer’s Body poster comes to life, and Megan Fox utters the words “dick in ass.”
“It’s rare to find someone who inspires you to bring your whole creative self to the table,” says Desiree Akhavan, the filmmaker who directed half of Overcompensating’s eight episodes. “Benny makes you want to match his funny, match his weird. I hesitate to use the word ‘magnetism’ because that can come across as schlocky or smarmy, but his is a magnetism that is rooted in something quite heartfelt and smart.
Whatever you call it, I can see why people want to be close to Benny’s drama. When I tell him at the wine bar that I have never been to Sqirl, an East Hollywood café that I had thought of as passé, he is brisk. “You’re not going to get judgement like that from me,” Skinner quips. “Come to L.A. I’ll drive you there. We’ll have the time of our life.” Our artichokes arrive, but it turns out they’re actually just artichoke dip. “Oh, this is about to be crazy,” he announces, with the reverence of a bachelorette party welcoming a fishbowl of liquor. “I thought we were getting, like, a flower! This is huge news for us.”
It took Skinner a while to get here. Growing up as the youngest of four siblings in Boise, Idaho, he began to understand that he’d have to tuck the shiniest side of himself away in order to get by when he was in the fourth grade. His parents had nurtured his inner performer, sitting through his childhood performances of “Oops! … I Did It Again” and buying him dolls to play with. “But they can’t protect you from school,” Skinner says. “You get into that classroom and you do The Lizzie McGuire Movie monologue, and your classmates are screaming about it, and you’re like, I need to shut that shit down.” (He chose a back and forth between Lizzie and Italian pop diva Isabella Parigi, roles both played by Hilary Duff. “Multiple characters,” he explains.)
He started playing football, shrouding his passions in shadow like the Abercrombie catalogues in his closet. At home, he gravitated toward TV shows like Gossip Girl and The O.C., as well as the movies of Robin Williams. “I would literally watch Mrs. Doubtfire every day,” Skinner says, nudging an artichoke sliver onto crostini. “He was everything to me. I think there’s so much brilliance in everything he does, the way he can play joy and sadness at the same time.”
To bring that kind of multifacetedness to his Overcompensating role, Skinner worked with Nancy Banks, the go-to acting coach of Margot Robbie and Emma Stone. “We were working on my voice in the show and I would do my ‘closet voice,’” he says. “It wasn’t exactly going deeper, but we wouldn’t let it go up. There’s no …” Flair? “No flair, because we’re not having any fun. I was just trying to be so vanilla and baritone. Hopefully you see that this character is dying to let something out.”
Skinner kept his sexuality a secret until his senior year of college. He says it felt suffocating. “It led me into a very deep depression,” he says. “I think anyone who’s experienced this knows that it feels all-consuming. It was life and death for me, and I was making myself really sick and so sad. I look back and I understand why I stayed in the closet, but of course, if I have one regret, it’s not coming out sooner. It’s just so crazy that something I thought would ruin my life would change my life and make my life worth living.”
There’s poignancy to Benny’s coming out in Overcompensating, but it’s mainly played for laughs, setting the stage for disastrous Grindr meets and an awkward reconciliation with an old flame. “The pathos of any coming-out story is there no matter what,” says Yang. “But Benny’s able to harness the feeling of walking through that crucible and how it has the potential to make you sharper, funnier, and just a better version of you. I think there’s something in this story that is kind of revolutionary, even though it feels so true as to be a given.”
“Getting it right for me is just, How specific can we go?” says Skinner. “There’s at least one other queer person out there who feels uncomfortable giving a straight guy a handshake. This is the panic that’s been going through my head for 20-plus years.”
When Skinner is in New York, he likes to walk down the street like he’s in a music video. “Any time I’m here I’m like, Fuck!” he says, with the fury of a mall punkette who just discovered that Hot Topic is sold out of arm warmers. “Putting my loafers on and stomping around like, Shiiiit!” He lived in Bushwick for two years after college. Soon after he arrived in the city, he met O’Connor at a house party. “Both of our Carmens introduced us to each other,” Skinner says with a smile. “I wonder if we saw that we were going through the same thing at the same time, because he had just come out as well.” They decided that they should go on their first date to a gay bar. They ended up at Manhattan legendary sleaze den The Cock. “We were so baby gays,” he says. “We learned all that together.”
Skinner’s early solo shows put a bizarro twist on pop-diva spectacle: In one 2018 performance, he descended from the ceiling in drag while singing Britney Spears’s “Lucky.” The following year, he and Mary Beth Barone co-hosted a monthly stand-up series named Cruel Intentions, a partial homage to Ryan Phillippe’s bare ass. Around the same time, Skinner began touring his own comedy show, a proto-version of the TV series he’s starring on today. It was a crucial step in him accepting what he calls “a coming-out story that feels very up and down and is filled with weird internalized homophobia and hatred of myself.”
Even so, another kind of self-doubt crept in. While Skinner was gaining a rapid following online — first on Dubsmash, then Instagram — he was nervous to call himself a comedian. After one tour date, Barone gave him a pep talk. “There is this weird thing with people who start on the internet and maybe don’t feel like they are quote-unquote comedians,” she tells me. “In Benny’s case, he’s earned it a thousand times over.”
Today, Skinner just sounds happy that the past is far enough in the dust to laugh at and twist into raw material for his next chapter. Happy hour is coming to an end, with tea lights appearing on the tables and couples cozying up over croquetas. “The scariest thing in the world to me was that someone would hear what my real voice sounded like. The scariest thing in the world,” he says. “So to be able to do that on the internet, publicly, and for people to be like, ‘This video made me laugh. Please make another one,’ kind of cleared any true fear I had.”
He says that those shame-filled years gave him the strength to handle anything in his career, whether that involves throwing a Coachella pop-up attended by Julia Fox or being in the boardroom for the business decisions required to make a show for the second-largest company in the world. “Going into an office every day and getting back into that corporate structure was random to a degree, for me,” he says. “It was a lot of panic attacks, but I’ve learned to just let it pass through me. It’s just my body reacting. Sometimes I have this thing of like, ‘If I’ve played football I’ve already done the thing I would have hated the most.’”
It’s also given him the confidence to stand behind an extremely queer show at an extremely not-great time for queer people. After Donald Trump won in November, Skinner sat down with his showrunner Scott King and talked about how Overcompensating might land differently under Trump’s administration. Filming was wrapped. In the coming months Amazon as well as dozens of other U.S. companies would announce rollbacks to their DEI initiatives. Skinner is careful to not overinflate the importance of a show in which an entire episode can revolve around the mistaken consumption of a weed brownie, but he’s happy that the show is coming out now. “If we can create any peace from this absolute clown parade, that would be great,” he says. “I think it’s amazing that we are releasing this show and being like, ‘We really don’t give a fuck. Eat it up.’”
