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The Worst Part of ‘Overcompensated’: A 31-Year-Old Playing a Teen

May 15, 2025
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The Worst Part of ‘Overcompensated’: A 31-Year-Old Playing a Teen
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Benito Skinner may be baby-faced, but you’d never take him for 18.

The internet comic’s new show Overcompensating, which is now available to stream on Prime Video, is loosely autobiographical. Skinner depicts a version of his own college story in the series: a football-playing juicehead suppressing his queerness. The main character even shares his name: Benny.

Skinner sets the show in his own college years, employing the whips and dabs trademark to the early 2010s. But much has changed since Skinner’s college years—including the actor himself. He’s now 31, with a chiseled jawline and porcelain skin. Where’s Skinner’s acne? Where’s his Freshman 15? Overcompensating puts an adult Skinner in kid clothing.

Dear Evan Hansen disease isn’t a fundamentally damning state. There are dozens of television shows—Gossip Girl, Buffy the Vampire Slayer—that miscast the characters’ age to great success. But Overcompensating has no standard. Mid-30-year-olds and 20-somethings play college kids alike. Sometimes those 30-year-olds play true to age, wholly disrupting the age spread.

Benito Skinner and Rish Shah in "Overcompensating."
Benito Skinner and Rish Shah. Courtesy of Prime

That forces Overcompensating into a sort of age blender, where the viewer is constantly second-guessing who’s an adult and who’s not. It flanks an otherwise hilarious show with a cloud of confusion.

Take Adam DiMarco. The actor has been on an infantilizing kick, fresh off his turn as post-college Albie on the second season of The White Lotus. Now he plays college senior Peter—while being 35 in real life. Overcompensating adorns DiMarco with the frat bro standards, from the scraggly half-beard to the perpetual backwards cap. It helps that his girlfriend is played by a 34-year-old, the series standout Mary Beth Barone. For a second, and just a second, these age placements are believable.

Cut to the Freshman pledge class, which DiMarco’s Peter helps to initiate. The secret society’s aspirants include Nell Verlaque and Kaia Gerber, both actresses with distinctly Gen Z faces. They have pouty lips and wide eyes, styles that only found their resurgence in the last five years. Clad in athleisure, the duo look certifiably young. And, at 24 and 23 respective, they are. Suddenly, DiMarco and Skinner’s millennialism is showing.

Mary Beth Barone in "Overcompensating."
Mary Beth Barone. Courtesy of Prime

These casting choices move from odd to uncanny when 30-year-olds play, well, 30. Hoping to explore his sexuality, freshman Benny sets up a hookup with an older man. He finds not one, but two: A married couple played by Matt Rogers and Bowen Yang. But, are they actually older? The comedians are 35 and 34, respectively. That’s 17 years older than Benny—but only 4 years older than Skinner. After the joy of the cameo fades, the viewer is left with more confusion than laughs.

The writing also challenges Overcompensating‘s age standard. Ostensibly set in the 2010s, the show is chock full of references that seem more appropriate for present-day college students. Charli XCX coming to a college town, for example, would spark mass fervor among current Brat-pilled college kids. But, back then, Charli was still rolling on the success of “Boom Clap.” Straight girls wouldn’t be manically rushing the stage.

Kyle MacLachlan, Benito Skinner, and Connie Britton in "Overcompensating."
Kyle MacLachlan, Benito Skinner, and Connie Britton. Courtesy of Prime

The age confusion is a frustrating outcome for an otherwise stellar series. There are genuine breakouts, both in Barone and Wally Baram, who plays Benny’s on-again-off-again best friend Carmen. The jokes operate at a high octane, pushing big laugh lines at a quicker and quicker pace. Skinner’s fans know that he has the comedic heft from his years of playing Kardashians on YouTube.

But these age mismatches crush the heart of Overcompensating. The viewer cannot invest in Benny’s college realizations, primarily because he doesn’t look like he’s in college. Nor can they invest in the show’s side characters, simply because their ages are splattered across two decades, destroying any sense of realism.

Sure, the jokes land. But the emotional resonance that Skinner clearly wants to strike has gone missing. Maybe some better casting would have helped.

The post The Worst Part of ‘Overcompensated’: A 31-Year-Old Playing a Teen appeared first on The Daily Beast.

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