The 71-year-old entrepreneur and reality TV staple, best known for Shark Tank, makes his acting debut in the new sports comedy, where he stars opposite Timothée Chalamet. In an interview ahead of the film’s Christmas Day release, O’Leary described the now-buzzed-about bare-butt paddle scene as “crazy” from start to finish.
According to O’Leary, the plan was to use a fake paddle designed not to hurt. That plan lasted seconds.
“It broke immediately,” he said, explaining that production quickly switched to a real wooden paddle with grooves. “That’s when things got real.”
Although there was a body double available, Chalamet insisted on doing the scene himself. The moment involves Chalamet’s character, Marty, begging for forgiveness from O’Leary’s ruthless businessman Milton Rockwell—and agreeing to a humiliating spanking to make things right.
“Timmy walks in and says, ‘No, it’s got to be my ass,’” O’Leary recalled with a laugh. “‘I’m going to immortalize my ass on film forever.’”
O’Leary admitted he tried to talk Chalamet out of it once he realized he’d be swinging a real paddle. Chalamet didn’t budge.
After about 20 takes, O’Leary said he could feel heat coming off Chalamet’s backside—but director Josh Safdie pushed for more intensity, telling him it didn’t look real enough.
“So I wound up like a baseball bat and nailed his right cheek,” O’Leary said. “That reaction you see in the movie? That’s real.”
Despite the pain, O’Leary was blown away by Chalamet’s commitment.
“I have a new respect for that kid,” he said. “He’s a crazy trooper. He deserves an Academy Award.”
O’Leary also praised Chalamet’s overall performance, calling it the best work of his career. He said the actor’s ability to improvise and stay fully in character gave the film its raw, electric energy.
“When he’s in Marty, he’s not Chalamet anymore,” O’Leary said. “Sparks are flying. If you’re in a scene with him, you better be ready.”
Marty Supreme follows the rise of fictional table tennis phenom Marty Mauser, tracing his journey from the Lower East Side to international competition. The film is loosely inspired by real-life ping pong legend Marty Reisman.
For O’Leary, stepping into scripted acting was a risk. He said even members of his own team warned him against it, doubting whether a reality TV personality could pull off a dramatic role. Still, curiosity—and a script he couldn’t put down—won out.
“I wanted to do something uncomfortable,” he said. “That’s how you keep life interesting.”
Though he initially clashed with the filmmakers over his character’s ending, O’Leary said collaboration led to a conclusion he’s proud of—and one that felt true to Milton Rockwell.
Marty Supreme opens in theaters on Thursday, December 25.
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