Shark Tank’s Kevin O’Leary steps into the spotlight in Timothée Chalamet’s high-stakes sports drama ‘Marty Supreme’

From the boardroom to the big screen, Kevin O’Leary is making one of the most unexpected career moves of the year. Known worldwide for his sharp-tongued deal-making on Shark Tank, “Mr. Wonderful” is trading startup pitches for vintage suits in the upcoming sports adventure comedy-drama Marty Supreme. 

Set in the glamorous yet cutthroat world of 1950s America, the film teams O’Leary with Oscar-nominated star Timothée Chalamet in a story that blends ambition, charm, and high-stakes competition. For O’Leary, the jump from reality TV to a prestige A24 production is as surprising for him as it is for audiences, but it turns out his casting was anything but random.

Kevin O’Leary’s role in Marty Supreme explored

As revealed by the businessman himself during an interview with TMZ, Kevin O’Leary plays Milton Rockwell in Marty Supreme, one of the wealthiest men in America during the early 1950s. The director, Josh Safdie, and co-writer Ronald Bronstein reportedly approached O’Leary looking for someone who could convincingly portray “a real a***hole,” and O’Leary admits he fit the bill perfectly. 

Rockwell, his character, is a powerful financier married to a glamorous movie star, Carol Dunne, portrayed by Gwyneth Paltrow. While the role is fictional, the opulent world Rockwell inhabits is rooted in historical detail, complete with lavish sets, period-accurate fashion, and even luxury watches from O’Leary’s collection.

The story follows Timothée Chalamet’s character, Marty Mauser - nicknamed “Marty Supreme” - a hustler with a dream of becoming a ping-pong champion. To get there, Marty must navigate the high society of 1950s New York, which leads him straight into the path of Milton Rockwell. Marty needs Rockwell’s plane and money to make his sporting ambitions a reality, setting the stage for a tense, comical, and unpredictable relationship between the two men.

According to O’Leary, filming in iconic locations such as Times Square and the Plaza Hotel transported him straight back to the city’s golden era. Chalamet’s commitment to the role is noteworthy as the actor trained for months under professional coaches Diego Schaaf and Wei Wang, both former players who pushed him to perform at a competitive level for the film’s intense sports sequences.

Chalamet’s performance, O’Leary says, is “Oscar-worthy,” and the movie’s blend of athletic grit, rich period detail, and eccentric characters promises a cinematic experience that feels both nostalgic and fresh.

Behind the scenes of Marty Supreme

The upcoming sports adventure comedy-drama film Marty Supreme boasts a diverse ensemble. Alongside Kevin O’Leary and Timothée Chalamet, the cast includes Gwyneth Paltrow, Odessa A’zion, Tyler Okonma, Abel Ferrara, Fran Drescher, Penn Jillette, Sandra Bernhard, Spenser Granese, Philippe Petit, and Luke Manley. Fran Drescher plays Mrs. Mauser, Marty’s mother, while Paltrow’s Carol Dunne embodies the grace and allure of a 1950s screen icon.

Directed by Josh Safdie and co-written with Ronald Bronstein, the film is produced by A24, with Chalamet also serving as co-producer. Darius Khondji serves as cinematographer, capturing the story on 35mm film to heighten the authenticity of its period setting.

Legendary production designer Jack Fisk has crafted an environment that transports audiences directly into mid-century New York, while Philippe Petit, the famed high-wire artist, is among the 140 non-actors featured in the film.

Principal photography began in New York City on September 23, 2024, and wrapped up on December 5, 2024, with additional filming in Japan completed in February 2025. According to Deadline Hollywood, the budget is $70 million, surpassing Civil War as A24’s most expensive film to date.

With Kevin O’Leary stepping into a role tailor-made for his on-screen persona and Chalamet leading an ambitious, genre-bending story, Marty Supreme is shaping up to be one of the most talked-about releases of the year. For fans of Safdie’s kinetic, character-driven filmmaking, this high-stakes sports drama promises to be as unpredictable as its larger-than-life characters.

Stay tuned with us for further updates.