Kevin O’Leary Says Playing Ruthless Villain Opposite Timothée Chalamet Was ‘Easy’

Best known to TV audiences as “Mr. Wonderful” on Shark Tank, Kevin O’Leary has made an unexpected leap into acting with Marty Supreme. The nerve-jangling drama marks O’Leary’s feature-film debut—and a sharp departure from his investor persona. Directed and co-written by Josh Safdie, the film follows an ambitious athlete, Marty Mauser, played by Timothée Chalamet, whose quest for greatness brings him into the orbit of a predatory sponsor.

A Villain That Felt Familiar

O’Leary portrays Milton Rockwell, a pen magnate who exerts control through intimidation and tests of loyalty. The role, O’Leary says, came naturally.

“I meet driven people chasing dreams every day,” he explained during interviews around the film’s release. “That dynamic—power, pressure, negotiation—felt very familiar.”

Safdie, known for casting nontraditional performers, sent O’Leary the script despite initial concerns from the entrepreneur’s team. O’Leary said the story’s intensity and Milton’s clarity of purpose convinced him to take the risk.

A Scene That Drew Attention

One moment in Marty Supreme has generated outsized discussion: a power-play scene that underscores Milton’s dominance over Marty. O’Leary said the production initially planned to use a double, but Chalamet insisted on performing the scene himself.

“It was about authenticity,” O’Leary recalled. “Josh wanted the audience to feel it, and Timothée committed to the moment.”

The sequence is framed to communicate control and humiliation without lingering on explicit detail, aligning with Safdie’s reputation for uncomfortable realism rather than shock.

Learning on a Serious Set

Despite this being his first acting role, O’Leary said the environment was focused and demanding. Multiple takes were required to achieve the right tone, and O’Leary credited the director’s precision.

“It’s a serious production,” he said. “You don’t show up to learn the basics—you show up ready.”

O’Leary added that working opposite Chalamet was a highlight, praising the actor’s intensity and preparation. He also shares scenes with Gwyneth Paltrow, who plays Milton’s dissatisfied wife.

What Comes Next

Since premiering at the New York Film Festival in October, Marty Supreme has drawn attention for its performances and Safdie’s signature style. O’Leary says the experience sparked interest in future roles, with new scripts already coming his way.

“I didn’t expect to enjoy it this much,” he said. “Interpreting a character, bringing your own edge—that’s compelling.”

Whether or not O’Leary becomes a regular on-screen presence, his debut underscores Safdie’s knack for unconventional casting—and O’Leary’s willingness to step far outside the boardroom.