Prime Video Promotes Popular Character to Regular Cast for Second Season of ‘Overcompensating’

The filming of the second season of Prime Video hit Overcompensating (2025– ) are in full swing. In addition to the return of several familiar faces from the first season and the addition of some new names, one of the notable side characters from the first season will have a bigger role.

University life full of chaos and self-discovery

The series is set on a college campus and follows Benny, played by creator Benito Skinner. Benny is a former football player and popular student who has not yet come out. When he befriends Carmen (Wally Baram), an ambitious outsider who wants to find her place at all costs, a chaotic, funny and recognizable story about identity, friendship and coming of age emerges.

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Overcompensating (2025‑ )

Former football player Benny struggles to accept his sexuality at university. He tries to present himself differently and therefore overcompensates.

Holmes is promoted to regular cast member

Actress and comedienne Chelsea Elizabeth Holmes, better known as Holmes, is now part of the permanent cast. She returns as Hailee, Carmen’s hilarious roommate, a role that was already loved by viewers in the first season.

Familiar faces

Mary Beth Barone, Adam DiMarco and Rish Shah also return for the new season. In addition, audience favorites from season one such as Connie Britton, Kyle MacLachlan and Lukas Gage make another appearance.

New faces

The series also welcomes some new characters. Tom Francis plays Declan Bishop, Aisha Dee plays Naomi and AnnaSophia Robb plays Chels. Patrick Regan, who was previously involved as co-executive producer, also appears in front of the camera as Preston this time.

Skinner remains a creative driving force

Benito Skinner will remain closely involved for season two as creator, writer and executive producer. The series is produced by A24, Strong Baby and Amazon MGM Studios, with Jonah Hill and singer Charli XCX serving as executive producers.