Why Was Benito Skinner Wearing A Portrait of John F. Kennedy at the Premiere of Overcompensating?

“Some people wait a lifetime for a moment like this,” sings one American Idol winner Kelly Clarkson in her debut single “A Moment Like This.” Last night in Los Angeles, at the premiere of the new comedy-drama Overcompensating, its creator, writer, producer, and star Benito Skinner found himself living his very own moment. Skinner is known to the chronically online as the celebrity impersonator extraordinaire “Benny Drama,” and has been a consistently hilarious presence in our social media feeds for around a decade. Needless to say, this has been a moment years in the making.
“I really think I will process this moment in 20 years,” he shares via email. “It’s not even a dream come true because this is so beyond anything I could have wanted. I’m just a gay boy from Idaho! Vogue, what the hell?!”
Overcompensating depicts the misadventures of Benny (Skinner), a closeted former football player desperate to fit in. It boasts a rather impressive and online-friendly cast that also features Adam DiMarco of The White Lotus fame, plus appearances from Kaia Gerber, Kyle MacLachlan, Lukas Gage, Bowen Yang, and even Charli XCX as either recurring characters or guest stars. “God I hope they laugh!” Skinner says, “and watch the show with their bestie in bed on a MacBook,” as one does! (But the “bigger MacBook that gives more of a TV screen vibe” he adds, explaining that “the show is pretty.”)
“I hope that people see themselves in any or all of these characters trying so desperately to be loved in all the wrong ways,” Skinner adds, turning reflective. Which makes one think—how much of this storyline is autobiographical?
“The specificity of my anxieties in the closet (a bro-shake, lying about loving Glee, rapping “Super Bass” [by Nicki Minaj, though you already knew that] to a room full of straight guys who thought I was having a psychotic break) are all eerily similar to my experiences in college,” Skinner writes. “I was inspired by relationships I had during the time, but I love writing characters.” He explains that he didn’t look to his own college friends for inspiration when putting together the ensemble. “It was so much more exciting as a writer to create them and their reasons for overcompensating from scratch,” he adds.
Last night Skinner attended the premiere wearing a custom ERL suit by Eli Russell Linnetz—a fitting choice, given that Linnetz often draws from the very same bro-erotic, frat-adjacent California aesthetic that Skinner leverages in the show. “I really am an OG ERL stan,” Skinner offers, “It had to be him! I think Eli is so brilliant and plays within this world of Americana but with a little unexpected (maybe even gay!) twist,” he continues. “The amount of cropped ERL football jerseys I have would send a chill down your spine.” (Scroll through if you find this hard to believe.)
The key detail was on Skinner’s back. His jacket featured an airbrushed portrait of none other than the 35th president, John F. Kennedy. “I saw Eli recently and we were talking about the look and he just said ‘JFK, right?!’ And I was like… ‘You know what… hell yeah,’” Skinner offers, explaining that his high school senior quote was one by Kennedy: “One person can make a difference, and every person should try.” “So DEEPLY self-serious for an 18-year old <3,” the man of the hour reflects. “But my stylist Jake Sammis and I loved that it felt like the Americana collegiate world of the show,” he explains, “And daddy JFK looks damn good in the portrait!”