How ‘Overcompensating' cast one of its writers as its co-lead

Yahoo

08-05-2025

Overcompensating is a new Prime Video series created by and starring Benito Skinner, who rose to fame on social media as Benny Drama. Casting director Jessica Kelly was not familiar with Benny Drama when the project came her way. Luckily, someone else in her life very much was.
"My sister is 14 years younger than me and she was constantly talking about this guy, Benny, on Instagram and his best friend, Mary Beth [Barone]. And I was like, 'OK, OK, OK,'" Kelly tells Gold Derby at our Meet the Experts: Casting Directors panel. "And then I was like, 'They seem cute,' but never really looked at it. And I had seen Mary Beth actually more — her stand-up would show up on my feed. And then I got this email about his new show and then I was like, 'My God, I'm going to be the coolest older sister ever.'"
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The comedy series, which drops all eight episodes on May 15, stars Skinner as Benny, a closeted college freshman who becomes friends with Carmen (Wally Baram), an outsider, on the first day. Barone plays Grace, Benny's older sister who attends the same college and dates another student, Peter (Adam DiMarco). Rish Shah plays Miles, a film student to whom Benny is attracted.
The Benny-Carmen friendship is the central relationship of the series, so nailing the Carmen casting was paramount. Kelly estimates they received more than 6,000 submissions for Carmen. Baram initially joined Overcompensating as a writer — her past writing credits include What We Do in the Shadows and Shrinking — before Skinner suggested her for Carmen.
"While he was in the writing room, you know, creating these characters with him as they're writing, and everyone just kept sort of looking at her when they would do quick read-throughs of scenes, like, 'Hmm, she's so Carmen.' And they mentioned that, but they were like, 'You know, we gotta make sure we do a process."
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Kelly had Baram, who had never acted before, film a self-tape and did a session with her. "It's such a different skill set to learn about how to audition and basically what acting is," Kelly says. "We just kept going through the process, kept going through the process. And Benny was like, 'You know, I just have had this feeling in my gut since the beginning, like, 'Let's try Wally one more time.' And then it went to being like, 'Try Wally like four more times,' just because of getting the right videos and angles and warming up and making her know that she has it all. It's all within her, and it's just finally putting her with Benny and them reading opposite each other. The character just started to flow. And then when I saw the trailer, I was like, 'Wow, you know, it looks like she's always done this.' Like this is just like a natural fit."
What put Baram over the top was the fact that she was not over the top. Skinner wanted the show to feel grounded and natural. "This was real people overcompensating for the things that they are embarrassed or vulnerable about, and that truth really had to be underneath every single character with a coat of what they put forward," Kelly says.
She points to Peter, which was written for "an aggressive frat guy." "We saw a lot of reads like that that were very good, but we didn't see that little twinkle underneath that let us know that there's something a little bit deeper going on," she says. DiMarco surprised Kelly and her team by adding more texture to the role. "Adam DiMarco had been on The White Lotus as the son, a little bit sheepish, a little bit dorky. And then he auditioned, and we were all like, 'Wow, he's a really attractive, strong guy and also so funny.' He just like would throw in a rap and make us all laugh. And it was just kind of one of those processes of seeing thousands and thousands of actors audition and and lots and lots of discussions."
One casting Kelly had no involvement in was Charli XCX's. The pop star plays herself and also serves as executive music producer. Skinner merely approached her at a party. "I did not have to do a thing there. It was all Benny," Kelly says. "And another reason why my sister is going to go absolutely crazy when she sees this show. Charlie XCX is also her other favorite person on the planet. But that was great."
Kelly did try to go after another pop queen. "We did really want to get Chappell Roan. I think that would have been really cool for some part. We tried many times when she was touring."
This article and video are sponsored content by Prime Video.
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