We're getting closer and closer to returning for another semester at Yates University in the breakout hit comedy series Overcompensating. The fan-favorite Prime Video original was renewed for a second season following the breakthrough and viral success of its first season, and as the cast and crew work on the new episodes, we just got the best news about the cast.
From creator, writer, and star Benito Skinner, Overcompensating takes place at the fictional Yates University as freshman Benny (Skinner) attempts to start over fresh after and remain in the closet to blend in at college. Along the way, Benny meets a number of memorable personalities who help him realize he shouldn't deny himself his truth, and one of those unforgettable people is Hailee.
Holmes joins Overcompensating season 2 main cast as Hailee
After Overcompensating became a viral sensation with its premiere in May 2025, the hilariously unfiltered and over-the-top character Hailee was an instant favorite with viewers. Going into season 2, our biggest wish was to receive even more Hailee, and that's what we're getting. Holmes, who plays the iconic character, has been promoted from recurring to a series regular for season 2.
Holmes joins the rest of the show's returning main cast, which aside from Skinner also includes Wally Baram, Mary Beth Barone, Adam DiMarco, and Rish Shah. Making the leap from recurring to series regular almost certainly confirms that Hailee could have her own storylines separate from Benny and her roommate Carmen. We'll be headed off on some wild misadventures with the show's best character.
Aside from the main cast members, Overcompensating season 2 has also been confirmed to have Connie Britton and Kyle MacLachlan returning guest and recurring stars as Benny and Grace's parents. We should also expect to see some more familiar faces back as Lukas Gage, Andrea Martin, Julia Shiplett, Nell Verlaque, Danielle Perez, Yasmine Sahid, and more are also reprising their roles.
Tom Francis, Aisha Dee, AnnaSophia Robb, and producer Pat Regan have also been added to the cast in guest and recurring roles. Francis will play Declan Bishop, Dee will play Naomi, Robb will play Chelsea, and Regan will play Preston. Further details about these new characters haven't been revealed, including how they will interact with the established characters.
The first season featured a number of brilliant surprise guest starring roles from the likes of Megan Fox, James Van Der Beek, Bowen Yang, Matt Rogers, Charli XCX, and more. Skinner likely has plenty of surprise cameos up his sleeve, and we're not so secretly keeping our fingers crossed for Charlie Puth to pop in for a scene after his name was one of season 1's funniest running gags.
Skinner spoke with People this month to tease what to expect in the "more queer" season 2 and shared his excitement for what's to come: "What we've done so far feels even more of exactly what I wanted to make. Everything feels really warmed up and everyone is just so funny and sharp. We didn't make a whole new show, but we did elevate it in a lot of ways. I think there's a maturity to it. I'm really excited — and it's nasty."
Overcompensating season 2 reportedly began filming in late March 2026 but was formally announced by Skinner on Instagram in April. The season will wrap filming sometime in June, and after that point, all of us fans can keep our fingers crossed for a hopeful (but currently unconfirmed) release date in late 2026. We'll share more news as it's announced by Prime Video!
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