Benito Skinner knows his way around a disguise. As his online alter ego, Benny Drama, he got famous for spoofing celebrities like Lana Del Rey and Kourtney Kardashian while also creating original characters like Kooper the Gen Z intern. Skinner’s sharp but never cruel content was rewarded with a massive audience on YouTube and Instagram.
When he began, Skinner was a Georgetown undergrad who’d grown used to wearing a different type of camouflage. Raised in Boise, Idaho, he spent much of his time and energy worrying that the whole world might discover he was gay. “I just remember the sense of doom anywhere I went,” he says.
Jacket and tie by Gucci; shirt by Polo Ralph Lauren.Photograph by Luke Gilford; styled by Jake Sammis.
Trousers by Saint Laurent by Anthony Vaccarello.Photograph by Luke Gilford; styled by Jake Sammis.
But at 31, all of Skinner’s masks are finally off. His new Prime Video show, Overcompensating, centers on a former high school football player who is desperately trying to fit in while struggling to accept his sexuality. Skinner didn’t just create and write the series; he’s also its star. “I really wanted queer people to see their experience and the complicatedness of that experience,” he says. “Not that I don’t think that exists, but I just feel like every time it was so much more complicated to come out than I’ve seen.”
Skinner attended Catholic school, where he realized that his love of choreographing dance routines to “Oops!…I Did It Again” and his obsession with Pocahontas would not be welcomed. So he buried his interest in the arts—and signed up for football instead. “You’re in third grade, and they’re talking about sodomites being stoned to death,” he says. “I’m like, I think I’m a little young for this, but I know that if I like men, I’m going to hell.”
Jacket and tie by Gucci; shirt by Polo Ralph Lauren.Photograph by Luke Gilford; styled by Jake Sammis.
While studying film at Georgetown, Skinner began to embrace performing (and making his first videos). In 2018 he hosted his first live show during the New York Comedy Festival and began performing comedy in front of audiences instead of just on the internet. He also started to write a script based on his coming-out journey and his relationship with his best friends. “We’ve seen that relationship being very high comedy,” he says, “but I feel like these women saved my life and allowed me to finally discover who I am.”
While making the latest version of Overcompensating, now being produced by A24 and Amazon MGM Studios, Skinner scaled back on social media videos. Being an internet star wasn’t always an easy gig, especially when it meant facing comments. “It’s so easy to take a critique personally,” he says. “Somebody commented once that I had super-dry butthole lips, and I was like, ‘Well, that will now plague me for the rest of my life.’ ”
Jacket, shorts, and tie by Gucci; shirt by Polo Ralph Lauren. Throughout: hair products by Bumble and Bumble; grooming products by Kat Burki.Photograph by Luke Gilford; styled by Jake Sammis.
Making Overcompensating allowed Skinner to create without all the extra noise. And while the show is centered on a queer journey, it also captures the universal desire to be accepted and loved. “I feel like the villain of the show in a lot of ways is this addiction to masculinity,” he says. “I think that everyone feels that, not just queer people.”
Now based in LA, where he lives with his boyfriend of eight years, Skinner hopes to continue making the show—he says he’s got at least four seasons in his head—but also to act in work by other creators. “I have a few things I’d love to do,” he says. “I’d love to play just full-on straight. Can you imagine?”
Hair, Kristen Shaw; grooming, Loftjet; tailor, Yelena Travkina. Produced on location by Petty Cash. For details, go to VF.com/credits.
