It’s a gloomy weekday afternoon in Manhattan but inside Boxers, a neon-lit watering hole that bills itself as “America's gay sports bar,” it might as well be last call.
The reggaeton’s blaring, the pool table’s buzzing, and our bartender, Javier? Stripped down to his boxers, welcoming the clientele with bedroom eyes, a half-fade, and abs you could grate a wedge of pecorino on. “Where’s your husband?” Javier asks a regular, a beefy unc in a plaid shirt and horn-rimmed glasses. “Don’t you want alone time with me?” the customer parries coyly. There’s a Mets vs. Marlins game on TV, but no one is watching.
It’s into this cabaret of masculinity that the comedian Benito Skinner makes his perfectly timed entrance, just as the opening strains of Jennifer Lopez’s “Waiting for Tonight” play over the speakers.
“Hey, baby,” he greets me, with an exuberant quiff straight out of a YM magazine spread and a goofy-handsome boy-band mug Lou Pearlman would scam for.
Skinner, who’s wearing a Celine shirt, JW Anderson jeans, and Noah loafers, is riding high from recording an episode of The Drew Barrymore Show. But it wasn’t exactly his first appearance on the program. In 2021, as his sweet-but-bristly celebrity impressions made him a social media star, Skinner appeared on the show dressed as Barrymore from Ever After and a year later, he returned in full TV Host Drew cosplay for a segment where the real Drew interviewed the fake Drew about his impressions. “You are pioneering something and this will get traced back to you,” Barrymore told him, presciently.
Today, Skinner was on the show as himself, Instagram’s favorite impressionist finally invited to the party.
It’s a heady time for the 31-year-old. Next week, Overcompensating, the half-hour comedy series he created, wrote, and stars in, will premiere on Prime Video with cosigns from industry giants like A24, Jonah Hill, and Charli XCX. The show has been a lifetime in the making, a hilarious piece of autofiction that also functions as a big career leap forward.
Overcompensating tells the story of Benny, a closeted college freshman still smarting from high school years spent as a jock and the valedictorian, inching his way to self-discovery.
Skinner drew inspiration from his own time in high school, when he was a secretly gay teenager in Boisie, Idaho, playing on the football team to keep up hetero appearances. “I mean, I distinctly remember a few moments where someone would pull me aside and be like, ‘You better like pussy,’” he says. “In those spaces, it's like, Well, be anything, but don't be fucking gay. Literally, the term ‘Don't be gay’ was said all the time.” Skinner sits up straight, doing his best Josie Grossie, imaginary fluffy pen in the air: “I'm like, all right, I'll take that note. Thank you.”
In college, he remembers getting drunk at parties in straight boys’ houses and finding himself in fratty bathrooms with posters of aughts-era bombshells like Megan Fox and Kate Upton on the walls around him. “I'd be like, ‘Hey, girls, I can't believe we're all here right now…” he recalls. “‘What a fucking bust.’” Now, of course, we find ourselves sipping soda water in the inverse of that situation: a gay bar that’s also a sports bar, where no one’s really watching the game but a few Lady Gaga deep cuts have already played.
Writing Overcompensating, Skinner looked to iconic teen movies like American Pie and Mean Girls as some of his inspirations: “I wanted that kind of classic American world—but now let's fuck it all up and let's tell different stories.”
Similar to those coming-of-age classics, the show is a true ensemble piece, with an assortment of hilarious, endearingly flawed characters that reinvigorate all the usual cafeteria archetypes. Mary Beth Barone, the cohost of Skinner’s podcast Ride, plays Benny’s uptight sister Grace, a college queen bee who draws her authority from her association with her frat king boyfriend. The frat king in question is Peter, a villainous douchebag played by The White Lotus’s Adam DiMarco. Wally Baram, a writer on the Jason Segel/Harrison Ford series Shrinking, nails her first ever acting role as Carmen, a wise if sometimes wide-eyed freshman. And the boy of Benny’s dreams? Ms. Marvel’s Rish Shah as Miles, the sweet, gorgeous film bro who our hero can’t seem to pin down. “All of them showed me things in the character that I thought were unexpected,” Skinner says. While none of them are household names now, there’s a sense that they’re one of casts that are destined to be everywhere very soon—like how it felt like watching that first season of Skins or the arrival of Girls.
Benito Skinner stock is looking bullish in general, with what feels like half of Hollywood betting on Overcompensating. Acting heavyweights Kyle MacLachlan and Connie Britton hilariously play Benny’s parents on the show, while other stars—from James Van Der Beek to Bowen Yang to Kaia Gerber to Megan Fox—appear in rip-roaring cameos.
Instead of period specificity, the show reaches for a feeling, the jagged vulnerability of coming of age, a time that can feel both like a raucous house party and a midnight drive alone that never ends. “I never wanted the comedy to get too big for how sad the emotions at times could feel in college,” he says.
Fittingly, Overcompensating is getting the kind of white-glove rollout that the season’s hot new show deserves, with a Coachella house (seen in the photographs here) and a multi-week college tour to help promote it. “It is literally feral,” is how Skinner describes the tour. “People are obsessed with getting me shots. I'm like, ‘Daddy doesn't drink like that.’”
“I'm thriving again,” Skinner says, about being back in college. “Not that I thrived the first time, but I can kind of rewrite it this time.”
Skinner became a social media sensation during the COVID pandemic, part of a new class of comedy stars borne out of the algorithm. They churned out scrappy, front-facing comedy when many big productions were derailed and provided a gloriously low-stakes distraction during a time when the whole world was doomscrolling.
Skinner was well positioned, thanks to a conversation he had with his boyfriend Terrence O’Connor—the digital strategist behind last year’s zeitgeist-defining Brat Summer and the pap picture–referencing rollout for the new Haim era—years prior. When they first met, Skinner confessed that he wanted to be an actor. “He was like, ‘Well, why is your Instagram private?’” Skinner says. “‘Trust me, you don't know anyone at agencies, your daddy is not in the industry, my daddy's not, no one around us is. You have no other entry point. But you clearly love doing something here.’” Skinner’s social media alter ego—Benny Drama, the Sasha Fierce to his Beyoncé—became the couple’s art project, their literal labor of love.
Skinner, a twunky Carol Burnett for the TikTok generation, thrived with impressions that were often cuttingly accurate but executed with the reverence of a true stan. Before long, the stars he was impersonating—from the Kardashians to Shawn Mendes to Barrymore—professed themselves fans of his comedy, and he earned follows from the likes of Madonna and Dua Lipa. In 2021, Skinner was even enlisted by the Biden White House for a video encouraging Americans to get the COVID vaccine.
But he soon found that the industry still had trouble envisioning him outside an iPhone screen. “I think I've reached my max here,” he remembers thinking, after auditioning for countless gay assistant roles. “I just think there are more stories to tell and more queer stories to tell.”
So Skinner went to work on a script that would tell his story and lean into his sensibilities, one that saw his experiences as a closeted gay teenager as the main story and not the B-plot. “I had this community that felt like it was rooting for me on the internet,” he says. “I was like, Fuck it, I can do it. Let's go.”
The first version of Overcompensating debuted in 2018 as a comedy skit about his time in the closet and all the ways he tried to remain in it, at the New York Comedy Festival. Like many queer people, Skinner is still grappling with the lasting effects of that time in his life. “The amount of internalized homophobia that I had to really untrain out of my body…” he says. “I remember on my first date with my boyfriend. I was like, Oh, his voice is higher than I thought. And I'm like, I can't believe I thought that…. This addiction to masculinity is so ingrained in all of us.” It’s also what’s given his comedy a purpose and an urgency.
As he got to work on the script that would eventually become Overcompensating the TV show, he realized the story he wanted to tell was actually about the friendship between gay men and straight women. He thought about his best female friends and the version of him they met in college. “This is exactly the moment where I was overcompensating and someone caught me,” he says. “It's those first people that you meet in college where you're like, Oh, you might love me even if I don't do this.”
For a lot of gay boys, those girlfriends provided a safe space that allowed them to tiptoe outside the closet. And for the girls? A loving male friendship that had no ulterior motives. “They allow themselves both to feel emboldened in their sexuality,” Skinner says. “It feels very, rooting each other on.”
The 1997 Julia Roberts rom-com My Best Friend’s Wedding was his proof of concept. The hat trick of My Best Friend’s Wedding is its ability to find a happy ending for Roberts’s Julianne, a character the audience has already seen commit ugly, selfish acts in a desperate attempt to win the guy of her dreams. At the end of the film, we see Julianne at a wedding, defeated and alone—only to be saved by a dance with her gay best friend George, played by Rupert Everett. “It’s the worst moment ever,” Skinner says. “Like, ‘Oh my God, I just got my heart broken, who do I want to see right now?’ I’ve got to see this gay guy. I’ve got to be with my girl. That scene clearly changed me chemically, I think, as a kid.”
In Overcompensating, the Julia Roberts to Skinner’s Rupert Everett is Wally Baram’s Carmen, a fellow freshman Benny befriends, their bond forged by playing the video game Slut Slayer: Berlin and lip-synching to Nicki Minaj’s “Super Bass” in a Domino’s parking lot. Carmen is the unexpected heart of the show, the person who sees our protagonist at his ugliest and most insecure and loves him anyway.
Skinner wrote the character as a tribute to his godmother, who passed away when he was in college. “Her name was Carmen,” he says. “That was maybe the first woman in my life who really saw me and wanted to preserve the things I was as a kid.”
One of the many paths to showbiz success is that of the auteur—those who write their way to their own breakthroughs, crafting projects that lean into their idiosyncratic points of view. It’s no coincidence that some of the best examples of this archetype are talents from marginalized communities—think Cole Escola, Issa Rae, Quinta Brunson—who sprinted through the rat race only to realize the lane they’re given has a dead end. Overcompensating is that for Skinner, a real showcase for his skills and sensibilities.
“I think I have a different way to give myself this chance and to also give the people who I'm really inspired by a chance,” he says. “Maybe I get to show you something that you didn't know was there, that I really know is there.”
Of course, putting the story down on the page is just one part of it. Next was building the team that would allow Skinner’s universe to come to life. After finishing his script, he began the process of bringing in his collaborators—one of the most crucial ones being Charli XCX. Skinner ended up pitching the show to the pop star at a party they were both at. “I had like two drinks that night, so I was fucking shit-wrecked,” he says. “She's like, ‘That's random as fuck, send me the script. Like, I can't believe you're telling me this at a party. Weird.’” Charli ended up signing on, as an executive producer, music producer, and as one of the show’s most memorable guest stars, playing a petulant diva version of herself begrudgingly playing a set for drunk college kids. “I'm going to make you a psycho bitch,” Skinner remembers telling her about the role. (His dream pop-star cameo next season? Lorde. “That's my hero,” he says. “The songwriter of our generation.”)
Around the same time, he landed crucial partners in A24 and Jonah Hill’s Strong Baby Productions, eventually finding a network and coproducer in Amazon Prime Video.
As Overcompensating went into preproduction, buzz around the show and its hot script began to build in LA. “I just remember there were some rumblings around town,” Rish Shah, who plays Miles, says in a video call. “Everyone I know was talking about Overcompensating. Literally everyone I know was taping for it, everyone was going up for it and excited about the scripts—which is rare…. This was just so refreshing and it had a very specific stamp on it.”
Baram remembers first reading Skinner’s script. “The pilot script that I read is such a perfect pilot script,” she says over a video call. “When I have friends in the future that are like, ‘I'd like to write a script,’ I'll definitely send them that script.”
Though Baram was initially referred to Skinner by A24 as a potential writer, after seeing her perform stand-up, he had a totally different vision in mind. “I went, that's Carmen,” he says.
For her part, Baram never thought it was a real possibility. The only real acting credit she had to her name was a Comedy Central sketch where she had a small role as a jogger who yells, “Get out of the way!” She calls herself “chaotically unprepared to act,” especially as the female lead of a TV show that was quickly shaping up to be a hot commodity. “You do this enough times where you're like, there's no way,” she says. “And then it came to fruition and I was very much stunned.” (She also ended up in the writers’ room.)
“That used to be what TV was all about, launching people,” says PEN15 veteran Daniel Gray Longino, who directed half of the season. “You'd start a show and you'd know them as their characters, and then they would become huge stars.”
Barone, meanwhile, gets the honor of playing this production’s Marnie Michaels—Benny’s sister Grace, a pretty, prissy know-it-all with major gaps in self-awareness. And true to form, Barone’s Grace gets her own Marnie-singing-“Stronger” moment. On Overcompensating, that comes in the form of a scene where Grace, back in their hometown and facing the peers who shunned her, tears into a cathartic karaoke performance of My Chemical Romance’s 2006 hit “Welcome to the Black Parade,” finally coming alive through the emo classic’s operatic emotion.
Barone, who on the show carries herself with the bearing of ’90s Gwyneth Paltrow, even when dressed as Alice Cullen from Twilight, confesses that she has control issues. “My comedy is very controlled. I'm always presenting myself a certain way,” she says. “So for me to purposely look bad or scream-sing a song that I am actually not good at singing, he was just like, I know you can do this, and I can't wait to watch. And having his confidence in me meant the world.”
Baram was similarly impressed by Skinner’s taste and willingness to collaborate. “I've worked with a couple of first-time showrunners, and I've never worked with someone like him,” she says. “Obviously, your first show is your baby. He was so willing and excited to bring in new ideas, and he trusted the people that he worked with—which is not an easy quality for a first-time showrunner”
Shah, who had the task of creating chemistry with the person he technically reports to, says Skinner’s generosity made the set a dream environment. “It was really special to go to a set where every single day I would forget that he's also my boss and this is his baby and his story. We all met as equals,” he says. “Everyone showed up every single day with a smile on their face. And I think that's why the show has these absolute zingers…. Benny has this ability to bring out the best in people.”
As the night progresses, the music gets louder in Boxers. We’re about halfway through Madonna’s 2015 track “Bitch I’m Madonna” when two bearded men start making out at the pool table, sipping beer between sloppy kisses. Back at the bar, Javier keeps the drinks flowing, dishing out tequila and pouring beer as his clientele gets more and more restless. (It’s still only, like, 6:30 p.m.)
Skinner is telling me about acting with the legendary Kyle MacLachlan when, suddenly, the unmistakable opening bars of Britney Spears’s “Crazy”—massive Max Martin piano chords like a jackhammer—plays over the speakers. Skinner is suddenly activated, fighting the impulse to give in to the song. “Can you imagine that?” he asks me, motioning to the stripper pole to our right. “Two seconds…I'm on!”
Toward the end of our time at the bar, I tell Skinner that this moment in his career reminds me of Tina Fey’s viral “I Don’t Think So, Honey” monologue from Las Culturistas last year. “I regret to inform you that you are too famous now, sir,” Fey advised Bowen Yang, months away from his turn in the blockbuster Wicked, about being too honest in his work. “Sshhhh, quiet luxury…. Authenticity is dangerous and expensive.”
It’s a quandary many superstar comedians find themselves at a certain point: So much of the best comedy comes from being an outsider, from the perspective of someone who didn’t have a table in the high school cafeteria, who stands right outside the velvet ropes. What happens when a comic is no longer on the outside? When the celebrities you used to impersonate are now peers?
For now, being incredibly busy has become a Band-Aid solution for Skinner. With all the work making and now promoting Overcompensating, he just hasn’t had the time to dip back into his elaborate impressions. “I haven't really done one in a while—and I do kind of feel like I sleep better at night,” he says with a laugh.
In any case, in this phase of his career he’s more interested in mining his own life for his art—and enjoying being able to be himself, no props required. “We've stopped overcompensating a little bit,” he says.
