Benito Skinner lands Attitude digital cover, talks Overcompensating and his ‘queens’ Charli xcx and Kourtney Kardashian
In this exclusive interview, Skinner also dishes on his fears that gay TV shows don't get properly promoted and how his boyfriend helped him grow as both a performer and a gay man
By Gary Grimes
There truly was something in the air in 2020 – and we’re not just talking about coronavirus. While the world was locking down, with most people confined to their home’s four walls for months on end due to the growing pandemic, a new class of comedians and writers were emerging as forces on social media. Jordan Firstman had a star-making performance as banana bread’s publicist, Megan Stalter was plaiting her hair to film a skit mocking corporate Pride speak, and Rachel Sennott was preparing to utter the immortal words: “Don’t have an eating disorder? Get one, bitch.”
Principal among this cohort was one Miss Benny Drama, also known as Benito Skinner. The Idaho-born actor and sketch comedian was enjoying a sharp spike in followers thanks to his short-form video content on apps like Instagram and TikTok, where he debuted original characters, including the deranged real estate agent Deliverance Richards, and dished out spot-on impressions of celebrities, like a then-newly minted rock chick Kourtney Kardashian and Shawn Mendes (who’s “just a guy… who loves music.”)
Today, Skinner has more than 2.5 million followers across both aforementioned platforms, and an Prime Video sitcom, of which he is both writer and star, about to drop. Called Overcompensating, the show is based on Skinner’s college experience, most of which he spent deep in the closet. The actor plays a version of himself, also called Benny, who fumbles his way through his first semester as he attempts to hide and suppress his sexuality at every juncture.
It’s not that long ago, however, that this was all just a pipe dream for Skinner and his boyfriend, Terrence O’Connor. “He’s the first person I really, out loud, told I want to be an actor,” he says, speaking to me over Zoom from Los Angeles. O’Connor, then a fledgling marketing agency exec, set about helping his boyfriend achieve his dream, beginning with one simple step – turning his Instagram account off private. “I feel like that was the only way,” Skinner reflects. “We didn’t know anyone in the industry. He was like, ‘We didn’t go to school for this.’ I studied Film and Media Studies at Georgetown, you know – that’s not [prestigious New York arts school] Tisch.
“I was editing videos for a startup, and I would go to work, make nothing, get a Dunkin’ Donuts coffee on my way home and edit all night,” Skinner recalls of his early days trying to make it in New York. “I literally stole a Wet n Wild red lipstick because I didn’t have any money, and I only ate bagels for a long time.” Slowly but surely, he began to garner attention online as people responded to his drag-inspired work. The experience was hugely affirming for him, both as a performer and a recently out gay man. Skinner credits his boyfriend for helping him develop both sides of himself. “I’d always been a performative person. It was just that I knew if I was on a stage, everyone would know I was gay,” he explains. “I had that feeling with the internet too, where I was like, ‘OK, I’m out to some family and friends. Do I really want to be out publicly on the internet?’ And I think in meeting him, I started to love being gay and started to love the gay parts of myself.”
After much graft, with Skinner tirelessly filming and editing while O’Connor ran paid campaigns on his videos or paid meme accounts to repost them, and a relocation to Los Angeles, both of their careers began to blossom simultaneously. Today, Terrence, or Terry as his boyfriend affectionately refers to him, is an in-demand creative director in the music industry, working with acts like Haim and Lorde, having made a name for himself as one of the creatives who helped Charli xcx bring her beyond-viral brat campaign to the masses.
The ‘party 4 u’ singer is a pivotal character in both of their lives and careers, as she also serves as both a guest star and an executive producer of Overcompensating. The singer looms large in the series – every episode is soundtracked by her back catalogue, and eagle-eyed Angels will quickly spot a Vroom Vroom-era Charli poster adorning the dorm bedroom wall of Carmen (Wally Baram), Benny’s burgeoning best gal pal. After an ill-fated “hail Mary” last attempt at sleeping with a woman, Benny eventually comes out to Carmen.
The artist is yet another red thread connecting Skinner and his peers. He, Firstman and Sennott are all regulars at Charli’s highly photographed afterparties. The brat artist provided the score for the 2023 queer comedy Bottoms, which Sennott starred in andco-wrote. She then returned the favour by appearing in the singer’s ‘360’ music video, alongside Julia Fox and Chloë Sevigny.
I’m curious to know why Skinner thinks Charli seems to have the Midas touch when it comes to tapping into the next big things in comedy. “She is endlessly curious and is such an artist in that way, and so tapped into everything,” he gushes about his close friend. “I got a DM from her six years ago, saying ‘I want to come to your show in London.’ I was doing shows at the Soho Theatre, and I think a friend had just told her, like, ‘This guy makes me laugh, you should go.’
“She couldn’t come, but I had put on a pre-playlist that was all her music, which, thinking back, can you imagine she had to sit before the show and listen to her own fucking stuff?” he laughs. “Actually, she probably would have loved that.” Ultimately, it is the star’s openness to new ideas that Skinner identifies as her greatest strength. “Anyone that comes to her, she hears them out… But yeah, she is the nucleus. She is mother in that way.”
As Skinner prepares to bring Overcompensating to the world, his comrades are also due to deliver major television vehicles this year: Megan Stalter will play the lead in the upcoming Lena Dunham-penned Netflix sitcom Too Much, while Firstman and Sennott will both star in Sennott’s as-yet-untitled series for HBO.
I can’t help but wonder if there is any competition between the Instagram Class of 2020? “I think we all do really different things,” Skinner tells me. “Of course, amongst queer people and women, I think no matter what, there is a thing in the back of your head that there can only be one,” he laments. “Gay men have trouble cheering on each other, I think. I find that in myself sometimes too, where I have to be like, ‘No, I also think the gay guy is funny.’
“It’s like a hatred of ourselves that’s indoctrinated in us,” Skinner goes on, “that when we see someone else be out or do these things, you do feel like, ‘Well, if you did that, then they won’t love me, and you got the one spot.’ You know, straight men get a thousand spots, but we only get one.”
Skinner takes a moment to dwell on the razor-sharp criticism he often faces from other gay men in particular. “It can be really disheartening when it’s the community that you’re a part of saying, like, the meanest thing possible,” he admits. “I don’t care what the Republican guy says, I’ve heard all that before, but when it’s somebody that you’re like, ‘Oh, fuck, I kind of made this for you,’ it can be sad.”
One element of Overcompensating, which began its life as a one-man comedy show, that is sure to delight its gay audience is its cast. Aside from Skinner and Charli, the show includes appearances from queer favourites including Kyle MacLachlan and Connie Britton, who play his parents; Bowen Yang and Matt Rogers as a volatile gay couple Benny encounters on his first Grindr hook-up; Megan Fox as a talking poster on his bedroom wall; and The White Lotus star(and recent Attitude cover boy) Lukas Gage as his hometown friend who is also his first brush with another gay guy. Stellar as the cast is, I can’t help but ask why, like so many shows of this ilk, all of these teenage characters are being played by people in their thirties? “Well, we join a long lineage of classics not sticking to the age that is in the show – American Pie, Grease, Glee, Euphoria, Mean Girls,” Skinner says with a giggle. “I mean, did I think this show would take this long to make? Probably not, but I also do think we’re dealing with some very dark and emotional and sexual experiences on the show, and I feel really lucky that a lot of us have had a little space and time to come back to and address with humour and emotion.”
Prior to Overcompensating, Skinner’s most significant television role – save for a memorable appearance with his one-time muse Kourtney on an episode of The Kardashians – was as Jack Cole Jordan, a recurring character on the ill-fated, though criminally underrated, Queer as Folk remake which premiered in 2022. Despite the show’s similarly stacked cast, (which included legends like Kim Cattrall and Juliette Lewis, hot new queer talent Johnny Sibilly and Ryan O’Connell, plus appearances from the aforementioned Stalter and Gage) and its association with not one but two beloved previous iterations, the series failed to find its audience and was cancelled after one season.
Skinner, who is charmingly self-possessed throughout our conversation, is wistful when I ask him where he thinks it may have gone wrong. “I wish I knew,” he says with a sigh. “A cynical side of me is like, ‘God, will people just not fucking promote gay things?’” the actor posits. “Naturally, people come to it with snark and are like, ‘That’s not my original Queer as Folk,’and it’s like, ‘Yeah, we never said it was? That’s not the point.’ I think people want to be critical.” But he maintains a positive outlook on the project. “I loved that show… I think a lot of stories were taken from us when that didn’t get renewed,” he says. “But God, if I knew why, I’m sure it would make me sick, so maybe I won’t dive into it too far…”
A cynic might also think that a reason to hope Overcompensating could prevail where Queer as Folk faltered is one key difference between the shows. Where Queer as Folk offered a smorgasbord of stories across the queer spectrum, Skinner’s show centres largely on just one gay character, with most of the other main players being straight – at least to the audience’s knowledge. The writer tells me that although he always knew the show would focus on his coming out experience, he also wanted to tell the stories of the straight women around him during that time in his life. “These women who were creating such safe spaces for me had all their own shit going on, and I didn’t know that much about all of it because I was so in my own world and fears and anxiety,” he explains. He notes, however, that he has “so many more queer stories to tell” should the series get a second season, in particular about the character of George, played by close friend Owen Thiel, seemingly the only out gay guy on campus. “These are just the first entry points,” says Skinner.
Although we have met other iconic TV gay guy and girl best friend pairings when their bond is already well established (Will and Grace, Hannah and Elijah), in Overcompensating we get to witness the foundations being laid between Benny and Carmen. Conversely, Skinner’s real-life bestie, comedian and actress Mary Beth Barone, is also present, playing his harsh, stony older sister Grace. A longtime collaborator of Skinner’s, Barone has also co-hosted comedy nights and two podcasts with him since 2019.
“I grew up with Amy Poehler, Tina Fey, Maya Rudolph and Kristen Wiig acting in each other’s projects. So I think it always felt like it was on the menu for me – if you get to do a project, you do it with your friends,” he says. “It was always going to be her as my sister, but she still had to audition. We did a chem read, which I’m obsessed with, especially given how we treat each other in the show, like, [the characters] kind of actively try not to have chemistry,” he laughs. “But I really am so inspired by her comedy.”
When we speak, it is less than 48 hours until Overcompensating, a project Skinner has been developing since 2018, will finally drop on Prime Video. After spending the best part of an hour exploring his journey to date, I wrap up by asking for one final reflection from him. Who does he feel has had a bigger impact on his career: Charli xcx or Kourtney Kardashian?
“Oh, my God, my two queens!” he gasps. “I think, on my life, Charli, because I love her, and that’s like a dear friend to me, and also given the relationship that she has with my boyfriend too,” he begins. “My career, though… I think we have to give it to Kourtney,” he admits with a grin, and adds: “I think Charli would rightly give that up to Miss Kardash, totally!”
Overcompensating is available to stream in full on Prime Video now.
This interview is taken from issue 365 of Attitude, on sale 4 July 2025. You can order copies of Attitude here and alongside 15 years of back issues on the free Attitude app.
