What the Hell Is Kevin O’Leary Doing in Marty Supreme?

“They said, ‘We’re looking for a real asshole, and you’re it,’” Kevin O’ Leary told TMZ about when Josh Safdie and his co-writer Ronald Bronstein approached him to play a key supporting role in their squalid, 1950s picaresque Marty Supreme. The film concerns a callow ping-pong prodigy (Timothée Chalamet) trying to scrounge together the money to play in a high-profile tournament in Tokyo. O’Leary plays a nasty high-roller debating whether or not to act as the kid’s benefactor.

Set a thief to cast a thief, as they say, and hire an asshole to play an asshole; sometimes, the simplest solution is the correct one. If O’Leary’s account lacks the apocryphal star-is-born romanticism of Lana Turner being scouted at a soda fountain on Sunset Boulevard or Harrison Ford cold-reading for Star Wars while installing doors for Francis Ford Coppola, the end result is still one for the books. “I think Ronnie and Josh did the right thing. Just saying, ‘Look, just be yourself and let’s see what happens,’” O’Leary said in that same TMZ interview.

There’s always been a line-blurring element to Safdie’s casting decisions; the movies he made with his brother Benny are rife with actors either playing against type (like Robert Pattinson as a hood rat in Good Time) or else celebrities doing imitations of themselves. But Arielle Holmes, the star-slash-biographical-subject of 2014’s Heaven Knows What, was an unknown: an uncut gem. O’Leary’s reputation is real and it precedes him in a different way than, say, Uncut Gems’ Kevin Garnett.

Between his right-wing political affiliations and his well-documented legal issues, O’Leary’s presence constitutes a real risk for Marty Supreme’s distributor A24; his press-tour soundbite that Safdie and his producers could have “saved millions of dollars” by swapping out mobs of period-garbed extras for AI-generated simulacra split the difference between genuine insufferableness and self-aware rage bait. (If you want to make people in the arts mad right now, try touting the virtues of AI.) What matters, though, is the performance, and O’Leary holds his own. In a movie that strives to allegorize American exceptionalism through the figure of Timothée Chalamet’s eponymous ping-pong wizard, it’s fascinating that an ex-Montrealer ends up giving the best Ugly American.

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In truth, it’s hard to think of a real precedent for O’Leary’s work here. It won’t do to compare him to other notorious non-actors who’ve shown up in a memorable movie, partly because this isn’t a metafictional gambit—like Jordan Belfort in the coda of The Wolf of Wall Street or Elon Musk stiltedly chopping it up in Iron Man 2—and partly because calling O’Leary a non-actor belies the nature of his shtick.

Nobody is suggesting that Mr. Wonderful is secretly a nice guy, mind you; the next former colleague or collaborator (or litigant) who makes that claim will be the first. But like all of the most successful reality television stars—including his pal Donald Trump, whose Canada-as-fifty-first-state rhetoric he has frequently echoed—O’Leary understands the power of embracing and amplifying caricature and how to turn the dial to eleven.

Back in 2017, his bid to take over the Conservative Party of Canada tripped up more over issues of bilingualism than charisma. In fact, he took such a big chunk out of his frenemy Maxime Bernier that he basically facilitated Andrew Scheer’s upset victory. If O’Leary had somehow run last year—French-language skills be damned—it’s worth wondering whether he’d have successfully channelled eight additional years’ worth of animus at the Liberals and rallied fractionally more support than Pierre Poilievre.

“You either win or you lose,” said O’Leary, in October, when asked about the latter’s prospects as party leader. “I don’t give a shit what the excuse is: You had a mandate, you failed, you get whacked.”

Fortunately, Safdie and Bronstein write better dialogue than that, and they’ve given many of the best lines to O’Leary’s character, Milton Rockwell—a fabulously wealthy, ethically bankrupt, designer-pen impresario who oscillates between being Marty Mauser’s benefactor and his bête noir. As well as his romantic rival: Marty is sleeping with Milton’s movie-star wife Kay (Gwyneth Paltrow) behind the latter’s back, and his confrontations with the older man are charged with suspense over the question of who knows what. Milton’s ruthlessness is exacerbated by his pronounced persecution complex—a provocative mix given the script’s explicit excavation of postwar Jewish-American identity. Safdie’s themes of upstart entrepreneurship and Darwinian, business-class metaphysics suggest nothing so much as Shark Tank by way of Philip Roth; in this equation, O’Leary is something like a scenery-chewing Great White.

He’s especially menacing in a sadomasochistic set piece that evokes his talent (if that’s the word) for public humiliation. Suffice it to say that there’s a significant portion of the internet that’d kill to take a crack at Chalamet in the same way O’Leary does here. In a movie about ping-pong, you’d better believe Safdie gets as much use as possible out of those paddles.

The cognitive dissonance of seeing Willy Wonka spanked by a former CBC News Network host is real and so is the quality of O’Leary’s acting—whether or not he’s being himself, he brings something real to Marty Supreme, which would be a far more innocuous movie without him. (If Chalamet ends up beating George Clooney for the Oscar for Best Actor, he’ll have to thank his co-star for making Marty look like less of an asshole by comparison.) In the end, Milton gets exactly what’s coming to him. It’s only fair that O’Leary receives similar treatment. We don’t have to have sympathy for the devil in order to give him his due.