It’s a typical frat party. As beer pong ends, the winner comes around the table to offer his friend, Benny, a consolatory dap. The light dramatically dims around the latter as the moment plays out in slow-motion. His gaze shifts from the hand extended towards him to his own. 

Facial expression shifting from dread to determination, dubstep in the background, he swings forward too eagerly and completely messes up the gesture. The recipient is clearly confused, but Benny doubles down by pulling him in, then attempts to play it off with a well-meaning shoulder punch.

The palpable awkwardness of the mutually aware error left unacknowledged is delicious. The scene is one of many closeted college experiences that Benito Skinner comedically retells in his Amazon Prime series, Overcompensating. The title pretty much spells out the premise of trying too hard. 

It’s barely the first time Skinner exaggerates playing it straight, in more ways than one. On YouTube, Benjamin Van Woostersen AKA Benny Brohana teaches you How To Talk Like A Bro. The caricature peppers his speech with unnecessary chuckles among other quintessential teen male mannerisms. That was eight years ago.

Thousands of BennyDrama7 Internet skits later, the 32-year-old now occupies a bigger screen. To date, he considers the show his most creatively fulfilling endeavour. “It’s so special to me, and also very vulnerable,” he speaks openly over video call, “It would be hard not to tie negativity towards it to my self-worth, because it’s so personal.”

The semi-autobiographical story intentionally retains some parallels while changing up other details. Intriguingly, deciding the main character’s name was never a question. “It’s funny, because most people call me Ben,” he reveals with an upturned smile on the subtle difference, “I had previously only done character work or impressions, so if this was my first emotional statement, it was gonna be honest.”

Skinner tries to write every episode as if it was the only season someone watched. Would it hook them? Would they feel everything that he would want them to feel? “I want every second to count. If people are giving you their time, it’s a—” he breaks to laugh at the unlikely severity of the word, “duty to make sure that they enjoy it.”

Writing is surprisingly—or not—the more challenging bit of the job. It’s the first chance he gets to truly process the emotions rooted in a significant segment of his yesteryear. He chuckles at how he couldn’t stop writing over Christmas because he simply couldn’t enjoy the day until he was satisfied with his progress.

Writing is also the most rewarding. “I love these scripts so much,” he enthuses, taking healthy pride in his work, “One of my favourite experiences creatively over the past year was just sitting down and hearing all these actors that I love so much deliver the lines for the first time at a table read. That was so amazing.”

While the hours are equally gruelling for acting, Skinner describes it as the fun discovery of what a scene could be. It is living out his dream, even if his body no longer knows what time of day it is after shooting. The reality of immortalising the highs and lows of his college life in mass media only hit him when he was reenacting them on camera. 

Highs include actually stealing a golf cart and driving it on the open road the first night he met his friend Nora, on whom the character Carmen Neil is based. On the flipside, rapping Nicki Minaj to a group of straight guys at pregame... to crickets. “They just didn’t get it, I guess,” he shrugs, before switching to flair, “because I thought I did a gorgeous job.”

It was a chapter of reckless abandonment that only the currency of youth could afford. An especially refreshing freedom when it stemmed from living in the same town up till then. The clean slate poses two options: Who do you pretend you are? Or do you finally become yourself? Skinner conceded to the latter, albeit gradually. 

Growing up in Idaho with no background or connection to the entertainment industry, the sheer opportunity now is very much a pinch-me situation. Sure, he studied film at Georgetown, but it’s no NYU or USC. Rather, the Internet provided the training ground.

“It was such a great place for me to discover my comedic voice and to learn how to perform and finally get all these things that I had hidden so deep within myself out of my system. Feeling like everyone could access it, that’s what I really wanted,” Skinner explains.

“It allowed me to incubate so many ideas. Hailee was one of the first characters I ever did. Now, she’s a character on Overcompensating, played brilliantly by [the mononym comedian] Holmes. I had so much time to explore that character, to then give her away to someone that I think is so genius is the greatest gift.”

The actor lists Issa Rae, Quinta Bronson, Ilana Glazer, and Abbi Jacobson as some of his heroes of the space. SNL definitely crossed his mind, and he did audition for other roles when he was younger and, in his hindsight, not quite ready. 

Yet, the path was somewhat laid out for him. He had already written the pilot, and was touring a standup with similar themes and tonality. His ticket to Hollywood? Precisely that online portfolio of crazy sketches. 

“I felt really proud pitching the show in meetings like, This many people have engaged with my comedy, and I can prove it. There’s an audience here, and I built it by myself. It gave me the confidence to think that I could make a show. I would have regretted it for a long time if I didn’t,” he expresses. 

There is a shorter lead time to the second season, but Skinner was able to complete it faster now that he was familiar with every actor. It was easy to jump back into the world because it was established, and the vision was clear to him long prior. Plus, simultaneously wearing the creator/producer hat acquaints him with issues that would arise and how best to shoot within allocated budgets.

This time, he’s supervising the music too. Charli XCX—who famously made a cameo on the first season after he pitched it to her while drunk at a party; the lore’s on the web—is still producing. “She is ultimately very busy, so we didn’t need to force her to go through Zooms for four hours. I was like, you’re putting out an album. What was so great is that she created the team that we have so that all stays the same.” 

Curating playlists and the right needle drops are another facet of the job that Skinner sincerely enjoys. In fact, he writes songs he wants for the scene into the scripts. The power of music to tell a narrative is more evident to him after the first season, but his passion for it came organically.

Besides having a cellist mother who puts on a concert every time he returns home for the holidays, Skinner played the piano as a child. “I think if I got to do Britney on the piano, I would have really sat with it. Um, Hot Cross Buns and Silent Night weren’t really doing it for me in a way that maybe like a Disney booklet could have,” he shares, half-deadpan.

And then came his checkered past as a radio DJ in college. Which, fun fact, marked the debut of his Benny Drama moniker. “I’ve certainly been obsessed with pop music my whole life,” he feigns a haughty air, “I know a lot of people judge pop music and I think they’re wrong, and I think they’re pathetic.” 

An early internship at Capitol Records lends to the possibility that he could’ve pursued a music-related career, so he’s thankful for this level of involvement in his work. “The only thing that’s semi-ruined for me is I can sometimes hear network notes when I watch TV. I know when there’s a branded spot, and they’re really good at it,” Skinner mentions one product placement that viewers have not noticed to this day, and instead misguessed others that were but nostalgic world-building elements.

A world that incidentally perpetuates a bunch of actors in their 30s playing college kids. “Oh, I’m so happy to be a part of this, let me tell you,” he jests, “No, it’s not something I thought that much about because I came up in an era of American Pie and Mean Girls. My favourite movie as a kid was Grease. I was used to people who were older playing younger.”

Skinner isn’t implying he looks the age; he just wants you to roll with it. It lets the actors take on the emotional challenges of that particular period in their life and be in on the joke, rather than having youngins doing the same on screen and seeming the butt of it. “I wrote this when I was 24, 25, ok, and TV takes a really long time. That’s all I’ll say,” he says in mock-defensiveness.

The new season promises more emotional scenes and physical comedy. The actor alludes to stunts and a harness. He was 50 feet up at one point, which doesn’t sound that high, but he swears it’s actually so high that he was so [insert your go-to expletive] scared.

It’s the joy of performing that counters plausible pigeonholing. If anything, Skinner is vocal about what he wants to try, and is happy to just, well, do it. As much as he is to run around Brooklyn all day in a wig like he used to. PS: If he had the energy, that is. PPS: Realtor Deliverance Richards is the persona he would bring out of retirement in that scenario.

He is also recently learning to let go of ingrained perfectionism. “Oh my God, the format of a photo will just make me sick to my stomach,” he exhales, “But I would be bad at my job if I tried to control every aspect. It wouldn’t be a great environment, which is about collaboration. Of course, I think some things will work, but I allow myself to be surprised and focus on making the most fun show possible.”

“I never thought I would be able to do this, so the fact that it’s real, I don’t know if I processed it, and I probably won’t for a long time,” he admits. For someone who is a little more subdued than his content may lead you to believe, Skinner still finds himself overcompensating every so often. 

“It’s really hard for me to feel like I could do less. We’re all told so many times a day all the ways we’re inadequate, and they naturally get stuck in your head. It is cathartic for me to write about it and forgive myself when I was doing it a lot. Understanding that some wounds you carry into adulthood, and having more tenderness when you see them because you know they’re not your fault.”

If the writing room is where he post-evaluates, on set is where he gets his giggles. “I’m getting paid to do this,” he remarks at the privilege of having laughter as a constant in his life—a rarity to most. “It’s a really terrifying time to be alive, and if we can give people a little break for eight episodes of TV that they can watch with their friend in bed, that feels like success to me.”

Photography: Jared Kocka at 11TH HOUSE AGENCY
Creative Direction: Asri Jasman
Art Direction: Joan Tai
Styling: Julian Fetterman
Hair: Ben Jones at THE ONLY AGENCY
Makeup: Charlie Riddle at THE WALL GROUP
Set Designer: Véné Castte
Executive Producer: Alex T
Producer: Nika Bregvadze at KYNN PRODUCTIONS
1st Assistant: Alexei Topounov
2nd Assistant: Hector Adalid
Styling Assistants: Lucas Randall and Vitória Diiulio
Makeup Assistant: Kayleigh D' Anne
Set Design Assistant: Atanasio Seferlis Jr.
Studio and Equipment: Yello Studio NYC
PR: imPRint