'Overcompensating" Cast and Characters, Explained

Cosmopolitan

16-05-2025

Social media and next gen comedy legend Benito Skinner is bringing his talents to the medium-sized screen with a new series, Overcompensating, now streaming on Prime Video. The show is an autobiographical satire of closeted young adulthood, performative masculinity, and the glittering, Everclear-soaked chaos of pre-pandemic college life.
Produced by A24 and Jonah Hill's Strong Baby Productions, the 8-episode series is a masterclass in Gen-Z casting, featuring guest appearances by the internet's babygirl Kyle MacLachlan, Connie Britton, Kaia Gerber, Owen Thiele, and even Charli XCX, who took on the role of executive music producer for the series. The main cast includes, obviously, Benito Skinner, as well as his frequent collaborator, Mary Beth Barone. Plus, White Lotus breakout Adam DiMarco and newcomer Wally Baram.
Here's a character-by-character breakdown of who's who—let's go back to college together.
Skinner plays a fictionalized version of himself: a former homecoming king and football golden boy from Boise, Idaho, who arrives at college determined to bury his sexuality under a mountain of Red Bull and hetero posturing. In bringing this Benny to life, Skinner tapped into his personal history as a closeted freshman at Georgetown, where he met a woman who would later become the first person he came out to. This Benny is equal parts deluded and endearing—his journey toward self-acceptance is the show's emotional core.
Skinner, best known for his viral character work as Benny Drama, is proving he's more than just a social media savant. He's a leading man with range, taking his signature satire and turning it into something tender.
Benny's first friend at the fictional Yates University is Carmen, a Jersey girl on the outs, hell-bent on fitting in—or at least surviving—with her dignity intact. In this role, she is that aforementioned friend who will change the trajectory of young Benny's life and identity.
Wally Baram, a stand-up comic and writer who's been featured on The Late Show with Stephen Colbert, never meant to be an actress, but was invited to audition while working in the Overcompensating writer's room. Mindy Kaling circa The Office, welcome back.
Grace is in her college cool girl era. She's cynical, protective, and played by Mary Beth Barone; a comedian best known for her 'Drag His Ass' breakup content and deadpan delivery. She is a longtime collaborator of Skinner's, and together the two host the popular podcast, 'Ride.'
Peter is Grace's boyfriend and an upperclassman idol at Yates. The campus golden boy who's oddly invested in Benny's well-being, he's played by Adam DiMarco. You'll remember him as Albie from season two of The White Lotus; or as the streets of Taormina know him, the mark of all marks.
Miles is the romantic tension we deserve: handsome, perceptive, and queer in a way Benny can't yet name. Their chemistry is magnetic, even when Benny's still in denial. Rish Shah, who made waves in Ms. Marvel, brings nuance to a role that could've easily fallen into 'hot guy' trope territory.
Esther isn't a person—she's a presence. As the leader of Flesh & Gold, a campus secret society, she runs Yates' social life like an occult priestess. Gerber – model, actress, and Gen Z royalty – slips into the role, giving bone structure and biting commentary.
Oh, and yes—Charli XCX shows up too. As herself? As a pop-culture deity? It's intentionally unclear. What is clear is that Overcompensating is just the beginning of something much bigger for Skinner and his cast. A show that dares to be cringey, flamboyant, and heartfelt all at once? We'll take ten seasons.