I don’t know about you, but I’ve developed a borderline unhealthy obsession with Amazon Prime’s new TV show, Overcompensating. And I say ‘unhealthy’ because 1) I’m already stalking following every single cast member (proudly watched every Benny Drama sketch), and 2) I’ve scoured every corner of the internet for even the tiniest morsel of behind-the-scenes tea and hilarious character trivia.
Everyone’s latest fave show follows a group of 20-somethings navigating messy friendships, complicated situationships, and chaotic life choices during their first year of college. At the heart of it all is Benny—a walking contradiction of confidence and self-doubt—whose attempt to hide his sexuality sets off a chain of painfully relatable and hilarious events. Think Glee meets American Pie, but with more queer chaos and Gen Z undertones.
Most critics have praised it, calling it “one of the most promising comedies to hit television in recent memory” (Roger Ebert), while others have called it “funny with flaws” (daleykryochek on IMDb—like, wut? just shut up already). But me? I’m ADDICTED. And truly, I’m not emotionally prepared to wait a whole year for season two (someone please hurry up and renew it for S2 already!).
So, if you’re in the same boat, desperately hoping Carmen and Benny patch things up or dying to know if Miles actually feels the same way Benny does, here are 12 super cool facts about Overcompensating to tide you over until next season. You’re welcome!
Everything You Want to Know About ‘Overcompensating’
1. The Show is Based on Benito Skinner’s Life
Main star of the show, actor Benito Skinner (who also wrote and produced the show, BTW) based Overcompensating on his own experiences in college. “I feel like I really based it on feelings and experiences and relationships, so like the coming out things were as honest and true as we could go,” Skinner told Today. “I did experience pretty much everything in the show,” he added.
2. Benito Skinner is Already a TikTok Icon
Did you know Benito Skinner was already a hot fave among Gen Z? That’s right, Benny boy is an IG and TikTok legend, known as Benny Drama, with a following of over 1 million people. The comedian gained popularity through his sketches playing original characters, like Jenni the TMI Hairdresser, and even celebrities like Shawn Mendes and Kim Kardashian. But before sharing his comedic talent on social media, Benito was very much afraid of being his true self.
“I’ve always loved performing, acting, doing impressions, and entertaining people. But then I definitely started getting made fun for it, so I sort of hid it away. I just locked that sh*t up for most of my young life, which was really sad,” he told Paper, adding, “I knew I wanted to do something in film, but I was too scared to be in front of the camera, because I was like, “‘The internet’s gonna say I’m gay.'” Thankfully, after coming out in college, Benito eventually decided to share his impressions on Instagram, which, FYI, immediately caught the eyes of stars like Dua Lipa and Madonna who started following him.
3. Benito Based Carmen on his Late Godmother
Skinner explained that the friendships he had with women during college were largely experienced through the lens of Benny and his best friend Carmen’s relationship. He revealed that he wrote Carmen’s character as a tribute to his late godmother, who passed away while he was in college.
“Her name was Carmen,” he told GQ. In the show, Carmen is the one person who fully accepts Benny for who he is—flaws, quirks, and all. “That was maybe the first woman in my life who really saw me and wanted to preserve the things I was as a kid,” he continued.
4. Two Cast Members are Stand-Up Comedians
No wonder this show has so much humor—two cast members are stand-up comedians! Mary Beth Barone, who plays Grace has comedy specials on YouTube, including Thought Provoking, and also happens to be a longtime collaborator of Skinner’s in his sketches. Together, they also host the podcast, Ride. Wally Baram, aka Carmen, is also a stand-up comedian, who starred in shows like Betty, Shrinking, and What We Do in the Shadows.
5. Wally Baram Started Off as a Writer on the Show
Working in the writer’s room for Overcompensating at first, Wally Baram never expected to end up as one of the lead, if not most cherished characters on the show. It was when Skinner watched her stand-up shows that he immediately decided to cast her as Carmen. “I related to her so much that when I had my meeting with Benny over writing, he was like, ‘You are kind of this girl,’” Baram told Marie Clare. “When Benny told me, ‘I want it to be you,’ my mind was tremendously blown. Even now, I’m still like, What the heck?”
6. Charli XCX is a Producer on the Show
One of the coolest freakin’ facts about Overcompensating? Charli (not Puth) XCX literally cameos as herself on the show. But did you know she also worked as an executive producer and music producer for the hit series?
Benito Skinner recalled meeting Charli at a party and offering her the role: “I had like two drinks that night, so I was fu**ing sh*t-wrecked. She’s like, ‘That’s random as fu*k, send me the script. Like, I can’t believe you’re telling me this at a party. Weird.'” Skinner also remembers telling her, “I’m going to make you a psycho bitch.” And that he did, because Charli’s character on the show gives moody diva at its finest.
7. Cindy Crawford’s Daughter Stars on the Show
Unless you’ve been hiding under a rock all these years, you already know that the beautiful Kaia Gerber is model Cindy Crawford’s daughter (she also dated hottie Austin Butler FYI). The 23-year-old model and actress actually stars in Overcompensating as the insufferable and pretentious Esther. Who knew Kaia could be so naturally funny, because this unserious role was kinda made for her…
8. ‘Lucky’ Was Used on the Show for a Reason
Overcompensating opens with Britney Spears’s 2000 iconic hit Lucky (following that epic George of the Jungle scene, ofc) and if you thought that was random (but cute) af, Benito Skinner is here to tell you it wasn’t. Skinner revealed that the Britney classic has a special place in his heart: “I think all these moments were kind of pivotal in my journey. Like, ‘Lucky’ was the song that I think changed my life in so many ways. As a kid, I was like, ‘Oh, I love Britney in a different way than everyone around me. I’m relating to this song in ways that no one else knows.’”
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9. Benito Got Megan Fox On the Show Through a Letter
Another random af moment on the show has to be Megan Fox’s hilarious cameo. Megan interprets herself in the form of a poster, giving Benny some much needed advice on how to pursue his crush, Miles. Benito told Elite Daily that the talking poster idea came from his experiences in college: “I’d go into a bathroom at a frat party and be surrounded by posters of all these women I loved, and I’d just be like, ‘Girls, I can’t believe we’re here. Let’s talk.’”
So, how did he manage to get the Megan Fox on his show? Benito actually wrote her a letter. “I sent a letter that said something like, ‘I love you so much. Will you please do this for us if you have one day?’ And Megan said yes,” Skinner said. “It felt so special and absolutely insane.”
10. Skinner Looked to Iconic Teen Movies as Inspiration
Skinner drew heavy inspiration from iconic teen films of the ’90s and 2000s when creating Overcompensating, especially cult favorites like American Pie and Mean Girls. Like American Pie, the show leans into unapologetically crude humor, while its over-the-top characters and satirical edge channel the chaotic spirit of Mean Girls. “I wanted that kind of classic American world—but now let’s fu*k it all up and let’s tell different stories,” he told GQ.
11. Holmes Wasn’t Initially Meant to Play Hailee
Let’s be real, can you picture anyone but Holmes as the iconic Hailee? Yeah, didn’t think so. It’s wild to imagine that Holmes (who uses she/they pronouns) originally auditioned for Carmen—a role that eventually went to Wally Baram. But Holmes made such a strong impression that the team asked her to read for Hailee instead, and the rest is history. Bonus fact: the unforgettable fake orgasm scene? Totally improvised. The crew laughed so hard, they kept it in.
12. Adam DiMarco Struggled Playing Peter at First
Most of us knew Adam as sweet, soft-spoken Albie from The White Lotus season two, so seeing him pop up in Overcompensating as Peter, the (hilariously loveable) douchebag, was a total curveball. His range? Insane. No surprise, then, that Adam DiMarco admitted he “didn’t know how to get into character at first.”
The actor also told The Hollywood Reporter that he was a “little unsure” about the role, as the “toxic college frat bro” character is “very different from anything I’ve done.” DiMarco then added, “it took a second to find it and then I read the scripts and I loved it. I thought it was hilarious.”
Until season two blesses our screens (and our souls), I’ll be rewatching Overcompensating for the third time, memorizing Hailee’s iconic one-liners (“Charli! Without your music, I would’ve killed myself!”), and probably listening to Britney and Gaga just for the mems. If you’re doing the same, just know: you’re not alone. We’re all just out here, overcompensating.
Let me know your fave facts about Overcompensating in the comments below!
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