In the midst of the Great Recession, Kevin O’Leary met Mark Burnett over breakfast at a beachside hotel in Los Angeles.
The 71-year-old venture capitalist known as Mr. Wonderful sold his education software company to Mattel for $4.2 billion, and in recent years has served as a member of the investor committee for the Canadian series “Dragon’s Den.” Burnett, the reality TV titan behind “The Apprentice,” was looking to bring the same entrepreneurial format to American audiences with a new series called “Shark Tank.”
“He said, ‘We’re looking for a real asshole, and you’re the one,'” O’Leary recalls, sitting in a Manhattan hotel room far from the Santa Monica sunshine in December. “I said, ‘Can I take that as a compliment?’ From then on, we never looked back.”
After 17 seasons and five Emmy Awards, “Shark Tank” has spawned nearly 45 international spinoffs and signed hundreds of deals. According to O’Leary, the show “changed elevator pitches forever.” His open ruthlessness also made him a celebrity and established him as the Simon Cowell of capitalism.
O’Leary is not an actor and claims Mr. Wonderful is not a character. (Yes, he’s the one who tells aspiring business executives, “You’re dead to me,” and calls them “greedy pigs” and “blood-sucking cockroaches.”) So it was a surprise when, 20 years after that breakfast in LA, he got a call from director Josh Safdie, who was casting the A24 film Marty Supreme, about a table tennis star played by Timothée Chalamet. Safdie uttered the same magic words as Barnett. “We’re looking for real bastards.”
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Despite having no acting experience, the creators of Uncut Gems envisioned O’Leary as the film’s central antagonist, a pen-selling millionaire WASP named Milton Rockwell who sparred with Chalamet’s hustler. Safdie asked O’Leary to come to New York to read for the role, but O’Leary refused. “I can’t do that. It’s the middle of summer. I’m sitting on the dock,” he told the director. “I’ll send you a plane. Come and see me.” O’Leary surmised that if Safdie was willing to fly to his lakeside house in Muskoka just to hear him read the role, the occasion must be momentous.
Safdie and co-writer Ronald Bronstein agreed and sent O’Leary the script, which he printed and placed in his bar. The next morning, O’Leary’s friend, investment banker Gene McBurney, was reading the script outside on the dock as the sun peeked over the water. “Have you ever read this shitty article?” McBurney asked O’Leary. “The person who wrote this is a very sick puppy, but I can’t stop turning the pages.”
O’Leary was sold. He read for the role and soon his agent began contract negotiations. “The usual Hollywood nonsense” ensued. But O’Leary’s agent wasn’t convinced it was a good career move for him. “He said, ‘I have to be transparent with you. Some of us at UTA are worried that you’ve never acted before. What if you mess up the bed?'”
“Marty Supreme” opened in theaters on Christmas and quickly became A24’s second-biggest opening weekend and sparked Oscar buzz. Most importantly for O’Leary, his acting has received rave reviews from critics. “This shit is starting to take effect little by little,” he smiled.
I first met O’Leary on a cold midtown morning. His flight had been delayed due to weather and he had just arrived with a suitcase in hand. He wears a black suit with skull-shaped cufflinks and shows me a pair of prototype earbuds, a gift from his “Shark Tank” co-star Mark Cuban, that translate his texts into five languages. O’Leary checked us in at the front desk, and I offered to sit at a table in the half-empty hotel restaurant. He grinned, shrugged me off, and suggested, “Let’s do it in the penthouse.”
In the hotel suite, O’Leary’s wife, Linda, insisted that I order coffee and snacks while O’Leary set up a small camera on a tripod. He said he was filming every interview, cropping it for his social media pages, and strapping a microphone to my jacket. It’s an unusual move that speaks to his passion for video production, and perhaps his desire for control.
He has a hard time explaining his acting process other than to say that he never felt like he was acting. When he walked onto the set with his hairpiece, glasses, and red watch (he now wears one on each wrist), he was Milton. “I just breathed the air of 1952,” he says.
The first scene he shot was opposite Chalamet. “We talked about the scene for a few minutes, and then he got up and walked around the camera a little bit and came back as Marty Supreme, and there were sparks flying from his fingertips,” he says. “I was blown away the first time we shot it. I’ve never been blown away again. I knew exactly how he worked, and it was great.” O’Leary is confident Chalamet will win the Academy Award for Best Actor.
In the movie, Milton mocks and marvels at Marty. In one particularly memorable scene, O’Leary smacks Chalamet’s bare butt with a ping pong paddle. According to O’Leary, the scene took 40 takes and was filmed until 4 a.m., but Chalamet refused to use a second butt because he “didn’t want to immortalize another butt on screen.” When the propeller paddle broke in one blow, Chalamet insisted that O’Leary use a real paddle, leaving him with a dimple on his cheek.
“It was easy to hit him because right out of the gate he was that arrogant bastard. That arrogant little mean bastard. It was amazing,” O’Leary says.
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In another threatening speech, Milton sneers at Marty and says, “I’m a vampire,” a line O’Leary thought up himself. He pulled out his text messages with Safdie and showed me a video of him getting into character that he had sent to the director. “We have a contract…and we sealed it with a paddle,” O’Leary said off-the-cuff, looking at his iPhone camera. “I was born in 1601. I’ve met many Marty Moser’s over the centuries.” Safdie and Bronstein loved jokes about immortality and incorporated them into the script.
However, O’Leary and the screenwriters did not agree on everything, and remain unhappy with the film’s ending, in which Marty holds his newborn child in tears, overwhelmed, scared, and euphoric. He has just flown in from Japan, where he refuses to lose and sabotages Milton in an exhibition match against his country’s star table tennis player, Koto Endo (Kotogawaguchi).
“I told them I was really unhappy with the ending. That my character was messed up like that. This Kumbaya ending is ridiculous,” O’Leary says. (He returned to this frustration five or six separate times during the conversation.) O’Leary feels that Marty “messed everyone up” in his relentless quest for success at table tennis, and feels “why shouldn’t he live a miserable life forever after that?”
O’Leary believes that not only Marty should suffer, but also his girlfriend Rachel, played by Odessa Azion. He proposed to Safdie the idea: “Rachel must die. She must die in childbirth.” (Safdie reportedly considered the proposal before deciding it was too “creepy.”) O’Leary also wanted the film to end with Milton literally biting Marty, and said Safdie and Bronstein “went as far as creating digital teeth” before negating the vampire element. “It may sound ridiculous, but to me it’s the right punishment,” O’Leary said.
For O’Leary, “Marty Supreme” marked his first stint as an employee in decades. “I learned the lesson that being on a movie set is not a democracy. I’m not used to being told what to do. I give directions,” O’Leary says. “We shot something 20 times, and I said to Josh, ‘Okay, I think I got it. You can move on.’ He said, ‘What the hell are you talking about?’ You can’t move on until I say move on. ”
Before amassing a nine-figure net worth, the Montreal-born O’Leary was a film editor who worked primarily in sports television. Photography has been his lifelong passion, and even though he has a personal marketing team, he still edits one social media post a week in Premiere Pro. (His online portfolio features dramatic black-and-white self-portraits, Canadian landscapes, and behind-the-scenes shots of Chalamet.)
I’m looking at the Safdies. Working with Aeroflex cameras, Panavision lenses, and 35mm film was a dream come true for O’Leary. But it was also painful at times.
“I’ve never seen so much inefficiency. The cinematographer was mad at me,” he says of Darius Khondji, who demanded perfect lighting for every scene. Shooting with one camera meant constant resetting between the two characters, and Safdie and Bronstein were “very crazy about perfection.”
“Then I saw the movie and realized the pure genius of this man,” O’Leary says of the director. “Every frame was perfect. The lighting was perfect. The scene was perfect.”
In October, O’Leary suggested in a podcast interview that Safdie could have saved millions of dollars by replacing thousands of extras with artificial intelligence. He argues that AI can be a useful background tool in entertainment. “During filming, we used blow-up sex dolls in the stands of hockey stadiums so people didn’t have to freeze for 16 hours,” he says of his TV editing days. “It was slightly out of focus. I couldn’t tell it was a sex doll.”
Still, O’Leary, a bullish AI investor, denies that the technology will have a significant impact on artists’ work. “I don’t think it’s going to be incorporated into filmmaking any time soon,” he says. “What makes actors magical is their lives, who they are, and what they mean to their fan base. It’s the same phobia we had when television made its way into radio: ‘Oh, this is going to destroy radio!’ No, it’s not. This art form exists today on a much larger scale, on earth and in space. To me, AI is just a tool.”
And while O’Leary says the growth of streaming and the decline of theatrical distribution is “obvious,” especially with Netflix’s impending acquisition of Warner Bros., he doesn’t think movie theaters will go away. “I go to these big screen formats and it’s not just the image, it’s the sound,” he says. “Even the most expensive home theaters (I have one) can’t give you the same feeling. As long as the experience is unique, you can’t beat this, especially in these new theaters with full bar service, food service, great sofa-like seating in a huge room with perfect sound and a 70mm size screen.”
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Even though it’s past the scheduled time at the hotel, O’Leary’s phone keeps ringing. “Let’s continue,” he said, flipping the device over on the coffee table. “We’re in great shape here.” But in the end, he hit the answer button. It was his publicist and he was late for another interview. “Okay, okay, okay,” he said quickly. “Okay, okay, okay. I’ll go. I’ll go. I’ll go now.” He looked at me without smiling and said, “We’re screwed.”
Linda brought me O’Leary’s breakfast – scrambled eggs, smoked salmon, and gluten-free toast, and I munched on some berries before rushing out of the penthouse. As O’Leary prepared for a junket interview, I asked him if it was a thrill to do press for a movie or if it was a chore. His wife answers for him: “He’s having the time of his life.”
O’Leary is keen to advance his career in Hollywood. Even before Marty Supreme was released in theaters, he had already received several offers from directors and producers who had seen early previews of the film. He plans to wait until the promotional cycle ends before deciding what to do next. “I’ve definitely realized that and I want to experiment with how diverse I can be in terms of the roles I play,” he says.
Still, there’s one area he’s particularly focused on.
“Ever since I was a teenager, I’ve always wanted to be a villain in a Bond movie,” O’Leary says. “I want to blow up shit. I can blow up a lot of shit.”
