At the height of the Great Recession, Kevin O’Leary met Mark Burnett for breakfast at a beachside hotel in Los Angeles.
The 71-year-old venture capitalist, known as Mr. Wonderful, had sold his educational software company to Mattel for $4.2 billion, and he had spent the last couple of years on a panel of investors on the Canadian series “Dragon’s Den.” Burnett, the reality TV titan behind “The Apprentice,” was looking to bring that 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 it,’” O’Leary recalls, sitting in a Manhattan hotel room in December, far from the Santa Monica sunshine. “I said, ‘Do I take that as a compliment?’ We never looked back after that.”
Seventeen seasons and five Emmys later, “Shark Tank” has spawned nearly 45 international spinoffs and struck hundreds of deals. According to O’Leary, the show “changed the elevator pitch forever.” It also made him a celebrity whose blunt ruthlessness cemented him as the Simon Cowell of capitalism.
O’Leary was not an actor, and he insists Mr. Wonderful is not a character. (Yes, it’s really him when he tells an aspiring business owner, “You’re dead to me,” or berates them as a “greedy pig” or “vampire cockroach.”) So, it came as a surprise when, two decades after that breakfast in L.A., he got a call from director Josh Safdie, who was casting “Marty Supreme,” an A24 film centered around a ping pong star played by Timothée Chalamet. Safdie uttered the same magic words as Burnett: “We’re looking for a real asshole.”
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Despite his lack of acting experience, the “Uncut Gems” auteur envisioned O’Leary as the central foe in the movie, a pen-hawking millionaire WASP named Milton Rockwell who spars with Chalamet’s hustler athlete. Safdie asked O’Leary to come to New York to read for the part, but O’Leary refused. “I can’t do it. It’s the middle of summer. I’m sitting on my dock,” he told the director. “I’ll send a plane for you. You come see me.” O’Leary surmised that if Safdie was willing to jet to his lake house in Muskoka just to hear him read for the part, the opportunity must be serious.
Safdie and his co-writer Ronald Bronstein obliged and sent O’Leary the script, which he printed out and left on his home bar. The next morning, O’Leary’s friend, the investment banker Gene McBurney, was outside on his dock, reading the screenplay as the sun peeked over the water. “Have you read this fucking thing?” McBurney asked O’Leary. “Whoever wrote this is a very sick puppy, but you can’t stop turning the pages.”
O’Leary was sold. He read for the part, and his agent soon began negotiating the deal. The “regular Hollywood bullshit” ensued. But O’Leary’s rep wasn’t so sure it was a good career move for him: “He said, ‘I have to be transparent with you. Some of us at UTA are nervous that you’ve never acted before. What happens if you shit the bed?’”
“Marty Supreme” opened wide on Christmas, quickly becoming A24’s second-biggest opening weekend and generating Oscar buzz. Most important for O’Leary, his performance has received raves from critics. “This asshole thing is starting to work for me a little bit,” he smiles.
I first meet O’Leary on an icy morning in Midtown, where he’s just arrived, suitcase in hand, after a weather-delayed flight. He’s wearing a black suit with cufflinks in the shape of skulls, and he shows me a prototype earpiece that translates his texts from five languages, gifted to him by “Shark Tank” co-star Mark Cuban. As O’Leary checks in at the front desk, I offer to grab us a table in the half-vacant hotel restaurant. He shrugs me off with a grin and suggests, “Let’s just do it in the penthouse.”
In the hotel suite, O’Leary’s wife, Linda, insists I order a coffee and a bite to eat as O’Leary sets up a small camera on a tripod. He films every interview and clips them for his social media pages, he says, pegging a microphone on my jacket. It’s an unusual move that speaks to his passion for video production and also, perhaps, a desire for control.
He struggles to explain his acting process other than to say he didn’t feel like he was acting at all. When he stepped onto the set with his hairpiece and glasses and red watches — which he’s wearing now, one on each wrist — he simply was Milton. “I just breathed the 1952 air,” he says.
The first scene he filmed was opposite Chalamet. “We talked about the scene for a couple of minutes, then he’d get up, walk around the camera for a second and come back as Marty Supreme. Sparks are flying off his fingertips,” he says. “The first time we shot, that freaked me out. It never freaked me out again. I knew exactly how he worked, and it was marvelous.” O’Leary is confident that Chalamet will win the Academy Award for best actor.
In the film, Milton mocks and marvels at Marty. In one particularly memorable scene, O’Leary smacks Chalamet’s bare ass with a ping pong paddle. O’Leary says the scene required 40 takes and shot until 4 a.m., and Chalamet refused to use a butt double because “he didn’t want some other ass immortalized” on screen. When the prop paddle broke after one hit, Chalamet insisted O’Leary use a real one, which left indents on his tush.
“It was easy to beat him up because he was that arrogant little bastard right out of the gate — that assumptive little prick. It was amazing,” O’Leary says.
Courtesy Everett Collection
In another threatening speech, Milton sneers at Marty, “I’m a vampire,” a line O’Leary came up with himself. He pulls up his texts with Safdie and shows me a video he sent the director of him getting into character. “We have a contract … and we sealed it with a paddle,” O’Leary improvises, looking at the iPhone camera. “I was born in 1601 … and I’ve met many Marty Mausers over the centuries.” Safdie and Bronstein loved the immortality quip and worked it into the script.
But O’Leary and the writers didn’t agree on everything, and he still gripes about the ending of the film, which sees Marty holding his newborn child, tears streaming down his face, overwhelmed, terrified, euphoric. He’s come straight off the plane from Japan, where he sabotaged Milton by refusing to lose an exhibition match against the country’s star table tennis player, Koto Endo (Koto Kawaguchi).
“I told them I was really unsatisfied with the ending, for my character to get fucked over like that. This kumbaya ending is absurd,” O’Leary says. (He circles back to this frustration five or six separate times throughout our conversations.) O’Leary feels that Marty “fucked everybody” in his relentless quest for ping pong success, and “why should he not live a life in misery in perpetuity after that?”
O’Leary believes not only Marty should suffer but his love interest Rachel, played by Odessa A’Zion, should too. He pitched Safdie on an idea: “Rachel has to die. She has to die in childbirth.” (Safdie allegedly considered the suggestion before deciding it was too “sick.”) O’Leary also wanted the film to end with Milton literally biting Marty, and he says Safdie and Bronstein “went as far as to make digital teeth” before nixing the vampiric twist. “I know that sounds nuts, but to me that would be the right punishment,” O’Leary says.
For O’Leary, “Marty Supreme” marked the first time in decades he was an employee. “I learned my lesson that film sets are not democracies. I’m not used to being told what to do. I do the telling,” O’Leary says. “We shot something 20 times and I said to Josh, ‘OK, I think we got it. We can move on.’ He said, ‘What the fuck are you talking about? There’s no moving on until I say we’re moving on.’”
Before he built up his nine-figure net worth, Montreal-born O’Leary was a film editor who worked primarily in sports television. Photography is a lifelong passion of his, and he still edits one social media post per week on Premiere Pro, despite having a personal marketing team. (His online portfolio features a dramatic self-portrait in black and white, Canadian landscapes and behind-the-scenes shots of Chalamet.)
Watching Safdie and co. work with Aeroflex cameras, Panavision lenses and 35mm film was a fantasy for O’Leary. But it was also, at times, a pain in the ass.
“I’d never seen such inefficiency. The cinematographer drove me nuts,” he says of Darius Khondji, who required flawless lighting for every scene. Shooting with one camera meant constantly resetting between two characters, and Safdie and Bronstein were “anally insane for perfection.”
“Then I saw the movie and I realized the sheer fucking genius of this guy,” O’Leary says of the director. “Every single frame was perfect. The lighting was perfect. The scenes were 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 maintains that AI can be a useful tool in entertainment for backgrounds. “I used blow-up sex dolls in the stands of hockey arenas when we were shooting so that people didn’t have to freeze for 16 hours,” he says of his TV editing days. “They were slightly out of focus. You couldn’t tell they were sex dolls.”
Still, O’Leary, a bullish investor in AI, rejects that the technology will meaningfully encroach on the work of artists. “I don’t think it’s going to be anytime soon that it’s integrated into filmmaking,” he says. “What makes an actor magic is their lives, who they are and what they mean to the fan base. It’s the same phobia we had when television hit radio. ‘Oh, it’s going to decimate radio!’ No it’s not. The art form exists today, even bigger, terrestrial and in space. To me, AI is just a tool.”
And while he says the growth of streaming and decline of theatrical distribution is “obvious” — especially amid Netflix’s impending acquisition of Warner Bros. — O’Leary doesn’t think movie theaters will go away. “I go to these large-screen formats. It’s not just the images, it’s the sound,” he says. “Even in the most expensive home theater — and I’ve got one — there’s no way you can get that same feel. As long as the experience is unique, particularly these new theaters with full bar service, food service, incredible sofa-like chairs in a giant room with perfect sound and 70mm size screen, you can’t beat it.”
Disney
We’re past our allotted time at the hotel, and O’Leary’s phone won’t stop buzzing. “Let’s keep going,” he says, flipping the device face-down on the coffee table. “We’re in a groove here.” But eventually, he hits the answer button. It’s his publicist, and he’s late for other interviews. “OK, OK. OK,” he says, hurriedly. “Got it. Got it. OK. I’m going. I’m going. I’m going right now.” He looks at me, without cracking a smile, and says: “We’re fucked.”
Linda brings over O’Leary’s breakfast — scrambled eggs, smoked salmon and gluten free toast — and I wolf down some berries before scurrying out of the penthouse. As O’Leary preps for his junket interviews, I ask if doing press for a movie is a thrill or a chore. His wife answers for him: “He’s having the most fun of his life.”
O’Leary is keen on growing his Hollywood career. Even before “Marty Supreme” arrived in theaters, he had already received a couple of offers from directors and producers who saw early previews of the film. He’s going to wait until the promotional cycle ends before deciding what to do next. “I’ve definitely caught the bug, and I want to see how diverse I can be in terms of what roles I play,” he says.
Still, there’s one part in particular he has his eyes on.
“My whole life, since I was a teenager, I’ve wanted to be the bad guy in a Bond movie,” O’Leary says. “I want to blow shit up. I could blow a lot of shit up.”
