It’s rare for someone to arrive at their so-called “big break” already backed by a loyal fanbase — but for Benito Skinner, the current moment feels less like a breakout, and more like a natural next step. His debut series Overcompensating premieres on Prime Video today, but if you’ve been online in the past few years, you’ve likely been watching him for a while.
Skinner, best known by his online moniker BennyDrama7, first made waves on Instagram with a stream of skits. From hyper-specific celebrity impressions, to fictional personas, his videos hit their stride during the pandemic and quickly became a balm for the deeply online. Then came Ride, his cult-favourite podcast with comedian and (now co-star) Mary Beth Barone. Each week, the two “ride” for a different topic — from the history of Jennifer Lawrence’s press tours to the concept of chairs — the more obscure, the better. Their dynamic is rife with inside jokes and niche references, but somehow still manages to feel inclusive, creating a rare digital space of humour and heart at a time when the internet feels increasingly hostile.
But arriving at this fiercely loyal fan base wasn’t always smooth sailing. And still, all these years later, no one is more surprised by the warm reception than Skinner himself. “I was so scared to post my videos or be ‘public’ on Instagram because of my voice,” he tells me. “I thought any time I would put on my wig or make a video they’d be like, ‘Go home, homo. We don’t want this.’ And instead, I feel like it’s become this community that’s helped me conquer myself — and the awful things I say about myself in my head.”
Clearly, Skinner’s vulnerability has paid off ten-fold. Now, he’s gearing up to expose yet another facet of himself, this time with his A24-backed auto-fictional series, Overcompensating. He’s breaking free from the confines of the internet and impressions, with a script that tells his story: in particular, coming of age as a closeted gay teenager. On the surface, it’s a hilarious comedy. But at its heart, the series is a touching, and at times heartbreaking, tale of the relentless desire to fit in.
While the show charts Skinner’s efforts to stay closeted, it’s also just as much about the friendship that slowly pulls him out — a bond rooted in the kind of intense, formative connection between a gay man and a straight woman that many will recognise, but few shows have explored with such specificity. That dynamic, between Skinner’s character and Carmen (played by Wally Baram), sits at the emotional centre of the series.
Baram, a stand-up and writer who originally joined the project as part of the writer’s room, was never meant to appear on screen. But after Skinner saw her perform standup, he knew she was Carmen. The chemistry between the two is clear — and, in many ways, mirrors the off-screen community Skinner has always built around him. On a recent college tour leading up to the show’s release, Baram found herself embraced by Skinner’s fanbase almost instantly. “I felt like I was a baby being introduced to the rest of the family,” she laughs. “They were like, ‘Oh my gosh, you’re Wally!’”
But telling this story — honestly, and in his own voice — wasn’t as straightforward as it sounds. When I ask if he ever felt underestimated in the process of writing the script, Skinner answers with the kind of self-awareness that grounds much of his humour.
“I did that to myself. I’m like, ‘You can’t do this,’” he admits. “And then I was like, you know what, before I pitch this, I just want to write the pilot. So if there’s ever a question, or if someone’s like, ‘Well, he just makes sketches on the internet,’ they couldn’t question it — the work was there.”
Clearly, plenty of people backed Skinner's vision. Among them, Charli XCX is not only a music producer and executive producer, but also guest stars in an episode (as herself, naturally). The ensemble cast is similarly stacked, from Kyle MacLachlan and Connie Britton as Skinner’s on-screen parents, to cameos from the likes of Kaia Gerber, Bowen Yang, and Megan Fox.
For those crossing their fingers for a season two, Skinner already has ideas about expanding his A-list ensemble. At the top of the list? His boyfriend's mother, who frequently lends herself to Skinner’s online skits. “We were going to get Terry’s mum in [season one], but she had a tee time. She’s very busy right now. Like truly, my girl has her days set, and I love that about her.”
And though he’s stepping into new territory, Skinner is doing it with the same wit, vulnerability, and self-awareness that first drew people in. If anything, Overcompensating feels like the project he’s been working toward all along — he just needed to live it first.
Images via @bennydrama7
