Kevin O’Leary is waving his “asshole” flag proudly this Christmas, but not in the way that you may be accustomed to.
In what might be the most WTF casting this year, the Canadian businessman-turned-TV-host, wannabe political leader and Trump pal features prominently in the new film Marty Supreme.
O’Leary may be most familiar for his stint as an investor on CBC’s Dragons’ Den, which he left in 2014, and the U.S. adaptation Shark Tank.
While he bills himself as Mr. Wonderful, it’s his blunt on-camera personality that he’s best known for. He’s leaning into the a-hole label as he promotes the film, joking to Vanity Fair that it’s “starting to work for me.”
But how on Earth did he even wind up in the Josh Safdie-directed movie, alongside stars Timothée Chalamet and Gwyneth Paltrow?
That’s what some film critics — and O’Leary critics — have been wondering.
“I was pretty stoked for this movie, but man Kevin O’Leary is just such garbage. Not sure if that’s genius stunt casting, but seeing him made my frown go upside down,” a Canadian Reddit user wrote on a thread titled, “Is anyone else bummed out about Kevin O’Leary being in Marty Supreme?”
WATCH | Timothée Chalamet, Gwyneth Paltrow and Kevin O’Leary star in Marty Supreme:
We need to talk about Kevin
The 101 on O’Leary is that the 71-year-old was born in Montreal and made a name for himself in the business world, co-founding the tech company SoftKey (later known as The Learning Company) in 1986 and selling it to Mattel 13 years later in a transaction worth as much as $4 billion.
He also started his own investment firm and from the 2000s onward became a fixture on television as a host of business shows, including the CBC News Network program The Lang & O’Leary Exchange, Dragons’ Den and Shark Tank, which airs on ABC in the U.S. and CTV in Canada.
O’Leary briefly campaigned to be leader of the Conservative Party of Canada in 2017.
He also made headlines for a 2019 boat crash in Ontario’s Muskoka Region that killed two people and led to his wife, Linda O’Leary, being charged. She was found not guilty of careless operation of a vessel in 2021.
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Kevin O’Leary (or “Mr. Wonderful”) is easily the most controversial Dragon who’s ever graced the Den. He gives a no-holds-barred account of his time on Dragons’ Den.
How O’Leary reined Supreme
Marty Supreme tells the story of Marty Mauser (Chalamet), a 1950s-era table tennis player convinced of his destiny as a generational talent.
O’Leary, in a supporting role, plays Milton Rockwell, a wealthy impresario who takes an interest in Chalamet’s Marty.
“In a world where you can hire any actor, choosing to cast Kevin O’Leary is as unserious as you can get,” Di Golding, a film critic and CBC Radio columnist, told CBC Ottawa’s All in a Day last week.
The cast of Marty Supreme in New York on Dec 16, from left: Tyler, the Creator; O’Leary; Gwyneth Paltrow; Timothée Chalamet; Odessa A’zion; Fran Drescher; Sandra Bernhard and Japanese professional table tennis player and actor Koto Kawaguchi. (Angela Weiss/AFP/Getty Images)
But Safdie said he needed someone in the role who could “evoke the ruthless American dream.”
“It was one of the harder parts to cast,” Safdie explained to CBC Radio’s Q. “[You need] someone who can communicate corporate colonialism, early globalism, ruthless businessman, cold corporate greed. And I met with actors and they weren’t right.”
He told guest host Talia Schlanger that O’Leary “instantly made every line better” when they did a read-through of the script.
LISTEN | Josh Safdie speaks with Talia Schlanger about the buzz surrounding Marty Supreme:
20:40Josh Safdie on Marty Supreme and the loneliness of chasing success
Although Golding wasn’t a fan, other critics have seen O’Leary’s casting as Rockwell as a success.
“All of O’Leary’s core characteristics are there: his political insensitivity, ruthless wheeling and dealing, and thirst for blood,” wrote The Cut’s Cat Zhang.
The film itself is getting generally favourable reviews — it has a 95 per cent fresh rating on Rotten Tomatoes — and it’s in strong contention to get a number of nominations at the upcoming Academy Awards.
And, if you’re wondering, studio A24 is promoting O’Leary for Oscar consideration in the best supporting actor category. Thus far, he has not been nominated for any of the key precursor awards and he is not among the top-tier contenders, according to leading industry publications and oddsmakers.
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What makes Mr. Wonderful a real …
O’Leary seems to want the world to know that Safdie and co-writer Ronald Bronstein were looking for a “real asshole” when they cast him, something he has recounted in interviews with The Hollywood Reporter, TMZ and others.
“I am not an asshole,” he explained to Vanity Fair. “I just tell the truth, and some people don’t like it. I think maybe I’m going to become the honorary chairman of all assholes everywhere after this. And it’s a job I’m happy to take.”
According to the Cambridge Dictionary, the word is a vulgar term used to describe someone considered “stupid or unpleasant” — and that’s how some people may mean it.
Other commenters on that aforementioned Reddit thread described him as “evil,” a “traitor” and even went so far as to say they won’t see the movie “specifically because of the casting.”
In the past year, in particular, he’s been a divisive figure for Canadians.
O’Leary is chummy with Donald Trump. He’s spent time at the U.S. president’s Mar-a-Lago resort in Florida, cheered for some MAGA policies and faced backlash for his takes on Trump’s repeated comments about Canada becoming the 51st state.
Kevin O’Leary paid a visit to Donald Trump’s Mar-a-Lago resort in Palm Beach, Fla., earlier this year, along with Alberta Premier Danielle Smith, amid the U.S. president’s tariff threats against Canada and repeated 51st state rhetoric. (Danielle Smith/X)
O’Leary’s former Dragons’ Den colleague Arlene Dickinson wrote in a LinkedIn post in March that his “whole brand is bombastic theatrics — big pronouncements with few facts, flashy takes and whatever keeps the cameras rolling on him.”
But it’s not just his business style and political leanings that get some people’s backs up.
He also made controversial comments earlier this year about Jeffrey Epstein, saying “nobody gives a poop” about the deceased sex offender who had connections to Trump, and adding of Epstein’s sex trafficking victims: “Maybe they were raped, maybe they weren’t.”
Even while promoting the movie, he raised some eyebrows by saying that A24 “could save millions” by using AI-generated extras instead of casting humans in background roles in films like Marty Supreme. He later said his remarks were taken out of context.
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