In the vibrant world of cinema, Kevin O’Leary, recognized as the ‘Mr. Wonderful’ of Shark Tank, has ventured into acting with a role in the film Marty Supreme. Directed by Josh Safdie, this movie is set against the backdrop of the 1950s, blending sports elements with drama and comedy. O’Leary portrays a wealthy tycoon named Milton Rockwell, marking a significant shift from his typical on-screen persona. This transformation has captured the attention of both audiences and critics.
The journey from investor to actor
O’Leary’s transition into acting is noteworthy. When approached by Josh Safdie, who candidly described him as a “real asshole,” O’Leary embraced the remark, humorously acknowledging that his forthrightness has shaped public perception. “I just speak the truth,” he remarked, showcasing his self-awareness, which has made him a compelling figure in both business and now on screen.
Character dynamics in Marty Supreme
In Marty Supreme, O’Leary’s character is a hard-nosed millionaire caught in a loveless marriage with Kay Stone, played by Gwyneth Paltrow. Their strained relationship serves as a backdrop for the ambitious young ping-pong player, Marty Mauser, portrayed by Timothée Chalamet, as he seeks greatness. The film intricately interweaves the lives of these contrasting characters, highlighting the tension between ambition and personal relationships.
Milton, O’Leary’s character, is intrigued by Marty’s talent yet remains skeptical of his intentions. Their exchanges are marked by sharp dialogue and palpable tension, showcasing O’Leary’s ability to embody a complex character. Milton’s assertion that he can “smell bullshit from a mile away” adds depth to the narrative, reflecting the cutthroat nature of ambition.
Behind-the-scenes insights
Collaborating with the creative team behind Uncut Gems offered O’Leary unique insights into filmmaking. Following an initial Zoom meeting, Safdie and co-writer Ronald Bronstein were impressed with O’Leary’s understanding of his character, fostering a collaborative atmosphere. O’Leary invited the duo to his lake house in Canada, where he provided valuable feedback on the script, underscoring his commitment to the role.
“I am Milton,” he declared, emphasizing the authenticity he brought to the character. His approach to acting was refreshingly straightforward; he opted not to hire an acting coach or seek advice from seasoned actors like Chalamet or Paltrow. Instead, O’Leary relied on his instincts and the chemistry he built with his fellow cast members, particularly observing Chalamet’s rigorous preparation.
Memorable moments on set
One particularly bold scene involved a late-night shoot where O’Leary had to deliver a surprising and humorous punishment to Chalamet’s character. In a black-tie setting, Milton instructs Marty to drop his pants, creating a comedic yet intense moment. O’Leary recalls breaking a prop paddle during a rehearsal, illustrating the dedication involved in capturing the film’s unique essence.
Additionally, the period-appropriate accessories, especially Milton’s watches, were carefully sourced, reflecting O’Leary’s commitment to authenticity. He collaborated with luxury brands to ensure the watches featured in the film were genuine artifacts, further enhancing its immersive quality.
Looking ahead
As O’Leary embraces this new chapter in his career, he continues to intrigue audiences in both entertainment and business. He has expressed interest in future collaborations with Safdie and Bronstein while emphasizing his commitment to authenticity. “I just try to be authentic,” he stated, reinforcing the importance of honesty and integrity in both his entrepreneurial and acting pursuits. With his unique blend of charisma, humor, and business acumen, Kevin O’Leary’s role in Marty Supreme signifies an exciting evolution in his diverse career.

