Kevin O’Leary of Shark Tank is accustomed to giving commands, but while acting in the new film Marty Supreme, the seasoned investor found himself in a position where he had to follow them.
For over a quarter of a century, O’Leary has been a millionaire and a dedicated investor. He sold his software firm, SoftKey, for $4.2 billion back in 1999. In his capacity as a Shark Tank judge since the show’s first season in 2009, he has since invested approximately $8.5 million into around companies.
However, while filming Marty Supreme, in which he portrayed the cutthroat millionaire businessman Milton Rockwell against Timothée Chalamet’s Marty Mauser, O’Leary discovered that being in charge in all other areas of his life did not translate to having authority on the film set.
(The following contains minor to major spoilers for Marty Supreme.)
O’Leary stated, “I learned my lesson that film sets are not democracies. I’m not used to being told what to do. I do the telling.” He recounted, “We shot something 20 times and I said to Josh [Safdie], ‘OK, I think we got it. We can move on.’ He said, ‘What the f*** are you talking about? There’s no moving on until I say we’re moving on.’”
O’Leary’s contributions to the film
Even though O’Leary wasn’t in charge on set, director Safdie and co-writer Ronald Bronstein were open to incorporating his input for a character that reflected parts of his own persona. A standout example was a monologue where Rockwell tells Mauser he is a “vampire” born in 1601.
O’Leary also had a hand in shaping Rockwell’s appearance, applying his expertise as a watch enthusiast to select the two timepieces his character wore, one set to New York time and the other to Tokyo time.
He declined to use a prop watch or wear any timepiece he did not personally own. This led him on an international search for historically accurate watches to feature in the movie.
He contacted Rolex directly and acquired a Patek Philippe from the 1950s, which he confessed he purchased “”. The other watch, a 1952 Seiko model named “Super,” proved unavailable on the resale market. Ultimately, “Seiko found one — it might have come from some museum — and they gifted it to me,” O’Leary informed the New York Times.
One of O’Leary’s most notable scenes likely involved him actually striking the Oscar-nominated Chalamet on his bare buttocks with a real ping pong paddle to enhance the realism of a crucial scene, which he said needed 40 takes and wasn’t completed until 4 a.m.
Certainly, a significant issue he had with the film was the conclusion, which ends badly for his character and which he described as “absurd,” as reported by Variety.
“I had lots of fights with Ronnie [Bronstein]— well, not fights, but I said, ‘Guys, this Marty Supreme guy, I would never let anybody [expletive] me over like this. This would never happen to me, ever. And he is not paying an adequate price,’” O’Leary told the New York Times.
However, the Shark Tank judge’s ideas were not all used in the final film. Reportedly, the investor and first-time actor proposed alterations to the ending, such as having the love interest of Chalamet’s character, Rachel Mizler (played by Odessa A’zion), die during childbirth to introduce more tragedy into an otherwise harmonious finale. Safdie ultimately reviewed the suggestion but deemed it too “sick” to include, per Variety.
A reluctant “employee”
O’Leary is unfamiliar with being an employee. Shortly before he sold SoftKey, the company had purchased numerous rivals and was ranked as the second-largest consumer software company at the time with .
In his role on Shark Tank, he is also accustomed to entrepreneurs approaching him for guidance, despite his frequently harsh critiques of participants. This includes the founders of The Lip Bar, whom O’Leary told “the chances that this is a business are practically zero.” The lipstick brand subsequently secured $6.7 million in a 2022 funding round and later mocked O’Leary in an ad campaign.
Director Josh Safdie recruited O’Leary for the part of Rockwell in Marty Supreme in part due to his Shark Tank persona. In fact, O’Leary says Safdie wanted him for the same reason TV producer Mark Burnett did for Shark Tank: “We’re looking for a real asshole,” Safdie allegedly said to O’Leary.
Safdie, the co-director of A24’s Uncut Gems, took a private jet to O’Leary’s lake house in Muskoka, Canada, to audition him for the role. As O’Leary openly considers more acting work (though he is reportedly waiting for the current promotional tour to conclude before accepting another part), he expressed his enjoyment of playing the villain and his ideal role would be a Bond villain.
“I say this asshole thing’s starting to work for me,” O’Leary told Vanity Fair.