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\n Kevin O\u2019Leary on the set of Marty Supreme.
\n Photo: MEGA\/GC Images\n <\/p>\n
Kevin O\u2019Leary is the reason for the vampire speech in Marty Supreme<\/a>. He\u2019s showing me evidence on his phone over the table we\u2019re sharing at an Upper East Side brasserie that\u2019s packed with ladies-who-lunch regulars. Marty Supreme is the story of Marty Mauser (Timoth\u00e9e Chalamet), a would-be table-tennis champion whose dreams of greatness are hampered by the fact that no one in 1952 New York City gives a damn about table tennis. O\u2019Leary, who plays a pen mogul named Milton Rockwell, believed so strongly that Marty needed to face greater consequences for what he does in the film that he kept sending director Josh Safdie in-character videos in which he aimed increasingly baroque threats at the protagonist.<\/p>\n The scene instantly cements itself as one of the movie\u2019s high points, an incredible non sequitur that I did not take literally, given that Milton \u2014 a real shithead of a plutocrat and the closest thing Marty Supreme has to a main antagonist \u2014 has no apparent issues with daylight, food, or sustaining a long marriage to his trophy wife, a former movie star played by Gwyneth Paltrow. But O\u2019Leary very much did. \u201cI wanted to bite him, have blood spurting everywhere,\u201d he informs me. \u201cIn fact, we went to the extent that we got a digitization of the vampire teeth to make the prosthetics.\u201d Safdie nixed the supernatural turn, for what everyone aside from O\u2019Leary would likely consider the better. But it remains a perfectly eccentric moment, the kind you can only get by packing a movie with performers<\/a> who are true characters themselves.<\/p>\n O\u2019Leary, who is better known as Mr. Wonderful to the Shark Tank viewers out there, arrives at lunch in a glossy black-on-black paisley suit jacket, looking a bit lord of darkness himself, despite his tan. (Like any self-mythologizing, right-leaning businessperson worth their salt these days, he\u2019s based in Miami.) Born in Montreal, O\u2019Leary initially made his fortune by founding and selling an educational software company that put out bulk titles on CD-ROMs, then established himself as a personality on reality TV, first on the Canadian competition show Dragons\u2019 Den and then on its American equivalent, Shark Tank, which he has been a part of since its inaugural season in 2009. Over the years, he\u2019s earned a reputation as the meanest of the titular sharks, its Simon Cowell, the angel investor who doles out harsh truths, ridiculous epithets, and elaborate metaphors to wannabe entrepreneurs.<\/p>\n Like the Joker, O\u2019Leary tends to give competing origin stories for his nickname. The version he tells me involves a sarcastic quip made about him by Amanda Lang, with whom he used to host a nightly business-news show on Canada\u2019s public broadcaster, the CBC, called The Lang and O\u2019Leary Exchange. Other accounts allege fellow Shark Tank investor Barbara Corcoran gave him the title in response to the zealous royalty deals he proposed to contestants in season one. However it came about, it\u2019s fair to say that \u201cMr. Wonderful\u201d is ironic. Fans have made compilations<\/a> of him calling contestants greedy pigs and telling them he\u2019d like to hire them just so he can fire them. With his dark suit and chrome dome, he\u2019s made himself into a comical avatar of ruthless capitalism, sneering at sentimentality and demanding to know \u201chow do I make money off of depressed people?\u201d O\u2019Leary considers his unfiltered criticisms on Shark Tank to be a service, a way of providing a necessary wake-up call when someone does not have a workable idea and is instead \u201ca loser pissing away their parents\u2019 mortgage money.\u201d<\/p>\n In other words, O\u2019Leary could be regarded as a professional asshole, which is what got him the part in Marty Supreme. \u201cI got a call from Josh, and he said, we\u2019re looking for a real asshole and you\u2019re it,\u201d he explains without a trace of self-deprecation. \u201cIt\u2019s not an insult to me \u2014 20 years ago, Mark Burnett said exactly the same thing when he was casting Shark Tank.\u201d It was going to be his first acting role, and his agent at UTA wasn\u2019t enthused about what the venture might do for his client\u2019s brand. \u201c\u2018We think you could shit the bed\u2019 were the words he used,\u201d says O\u2019Leary. Instead, he is startlingly great in the film, which rises up to cradle his presence like it\u2019s an inlaid gem. Milton \u2014 sporting a toupee, an air of smarm, and a sneer that tugs at his upper lip in a way that looks involuntary \u2014 is an off-putting counterpoint to Marty\u2019s win-at-all-costs version of American exceptionalism \u2014 a man for whom everything is transactional, including the death of his son in the war, for which he expects a thank-you from an Auschwitz survivor he meets.<\/p>\n O\u2019Leary isn\u2019t the only nonprofessional in Marty Supreme\u2019s sprawling cast, which includes rapper Tyler the Creator, real-life table-tennis champion Koto Kawaguchi, filmmaker Abel Ferrara, and supermarket magnate John Catsimatidis. But he\u2019s the one who has to go toe-to-toe with a career-best Chalamet in a series of escalating showdowns in which their characters compete for dominance. One encounter takes place in a restaurant in Paris not dissimilar to the one we\u2019re eating lunch at in New York, during which Milton offers to pay Marty to participate in a promotional event in Tokyo, a prospect Marty finds so offensive (he\u2019d be expected to throw the match to keep Japanese audiences happy) that he retaliates with a crude comment about Milton\u2019s son. O\u2019Leary\u2019s Milton goes still while remaining visibly incandescent with rage. It\u2019s one of the reasons that, after the screening, a documentary producer who is apparently not a reality-TV fan asked me, wonderingly, \u201cWho is that actor? What else has he done?\u201d<\/p>\n That O\u2019Leary could waltz into his acting debut in the movie event of the season is a testament to the certainty he exudes across the table from me like light from a SAD lamp. He\u2019s honed his tough-talking image over years on television, including tireless appearances as a talking head on news shows and a brief flirtation with political candidacy in Canada. In person, he gives a less confrontational version of the bombastic bluntness he affects onscreen. Mr. Wonderful isn\u2019t a persona, he explains, so much as the result of realizing that whether people love to loathe him or loathe that they love him, it\u2019s all better than indifference. \u201cHere\u2019s what I figured out,\u201d he explains evenly as he delves into a salad. \u201cI only need to keep 25 people in my life happy: my immediate business associates and my family. I can\u2019t make 11 million people happy. I have a lot of respect for people \u2014 and I get this every day \u2014 that write a full essay about how much they hate me. Imagine the amount of energy to compose that.\u201d<\/p>\n @kevinolearytv<\/a> <\/p>\n It’s a new name for an old idea. Shakespeare wrote outrageous things to sell plays, and ever since then, when the printing press was invented, people wrote outrageous things to sell books, and they always will. The internet’s just another distribution vehicle. The idea of controlling speech online has been elusive. In even China, it’s really difficult. The only option you have is to actually shut it down. Once it’s out there and once people have a VPN or ability to go around the IP that’s been shut down, they get access to it.<\/p>\n \u266c original sound – Mr. Wonderful<\/a> <\/p>\n O\u2019Leary is a well-known wine guy, which is why we end up ordering a bottle of Puligny-Montrachet to share over orders of French onion soup and beef bourguignon. He\u2019s a well-known watch guy, too, who has chosen to accessorize his monochromatic outfit with a vintage pair of red-leather bands \u2014 wearing two watches at a time is one of his signature moves \u2014 and talks me through their provenance with the practiced ease of someone who\u2019s been delivering this explanation a lot lately. He didn\u2019t want to wear rented watches in Marty Supreme, so he went through the trouble of personally obtaining a rare set that would make sense for the postwar-period setting \u2014 one a Patek Philippe; the other, which has a Japanese flag imprinted on it, gifted to him by Seiko with the understanding that it would appear onscreen.<\/p>\n What makes O\u2019Leary feel a little more palatable than some of his fellow moguls turned celebrities of the kayfabe economy is that, despite his love of punditry, he\u2019s not really a culture warrior. During his run for leadership of Canada\u2019s Conservative Party in 2017, he skewed fiscally conservative and socially liberal, proclaiming his opposition to carbon taxes and regulation and his support for LGBTQ+ and abortion rights. (How serious his commitment to becoming a politician was remains unclear, but he appears to have dropped out rather than learn the French necessary to win support in Quebec.) He\u2019s broadly anti-union and harps on urban crime, then he advocates for bank failure. He has supported Donald Trump in the past, though lately he\u2019s been more critical of the American president, especially when it comes to tariffs, certain immigration policies, and the government\u2019s investment in Intel. On the Marty Supreme campaign trail, he offered cryptic assessments<\/a> of J.D. Vance: \u201cI think anybody that is as close to the sun as he is has done a masterful job at staying out of trouble.\u201d<\/p>\n The actual business advice O\u2019Leary doles out on his social-media channels tends to run toward old-fashioned urgings \u2014 to not commit to mortgage payments that are more than 30 percent of your income, to save another 30 percent and invest it \u2014 suggestions that no one would quibble with in spirit, even if they have become difficult to impossible to follow in practice. Outside of X and Meta, he stays close to the headlines, if not squarely in them. In 2019, he and his wife were involved in a fatal boating accident; Linda O\u2019Leary was eventually found not guilty of careless operation of a vessel. In 2021, O\u2019Leary became a paid spokesperson and investor in the crypto exchange FTX and lost millions in the company\u2019s collapse. He was part of the People\u2019s Bid for TikTok in early 2025, offering $20 billion in cash to take control of the platform, but no deal closed. He has since come out as a proponent of artificial intelligence, and he believes more movies could be made if filmmakers embraced AI extras<\/a>.<\/p>\n