Marty Supreme: The Story That Proves Casting Kevin O’Leary Is Harder Than Casting Timothée Chalamet
A24’s Marty Supreme just pulled off its boldest play yet: prying Kevin O’Leary out of the boardroom and into a volatile role—a casting gamble that makes landing Timothée Chalamet look easy.
File this under sentences I did not expect to type in 2025: the hardest get in A24 and Josh Safdie's new movie was not Timothee Chalamet. It was Kevin O'Leary. And yes, they really had to go full movie mission to reel him in.
How they actually landed Kevin O'Leary
Writer-editor-producer Ronald Bronstein says the usual route went nowhere. They called O'Leary's reps, got a hard pass, and decided to cut around the traffic. They contacted O'Leary directly. He would not Zoom. Instead, he offered to send his plane, fly them to his lake house, stash them in a cabin for the night, and meet in the morning. By sunrise he had blown through the script and showed up with notes. That is not a cameo flirt—that is someone auditioning by force of will.
'We are looking for a real a**hole, and you're it.'
That is how Safdie pitched O'Leary the part. O'Leary, predictably, did not wilt. He leaned into it, cracking that the a**hole persona works for him, then insisting he is just blunt and some people do not like blunt. Either way, the guy understood the assignment.
The role: not a novelty act, an actual character
O'Leary plays Milton Rockwell, a loaded New York fixer whose marriage to Gwyneth Paltrow's Kay Stone looks more transactional than soulful. Milton is the kind of operator who treats Chalamet's hustling upstart, Marty Mauser, like a sketchy pitch: he claims he can sniff nonsense from a mile out and acts accordingly. The trailer backs up the idea that this is not a quick wink at the camera—O'Leary's name hits fifth, right after Safdie, Chalamet, Paltrow, and Odessa A'zion.
Safdie's preferred ecosystem is back too: cinematographer Darius Khondji says they folded in roughly 140 non-actors this time. It is a dice roll that paid off in Uncut Gems, and O'Leary slides right into that rough-cut energy.
Off-screen O'Leary stays... O'Leary
He is not soft-pedaling anything away from the set either. Politics, AI, truth-telling—he is perfectly fine being polarizing. His stance in short: some folks will hate it, some will love it, and he is going to do it anyway.
Chalamet hears the noise and doubles down
Chalamet, meanwhile, has spent the Marty Supreme press tour catching heat for the swagger—ever since his SAG Awards comments, the confidence has been its own storyline. He is not apologizing for any of it. In his words, the big, loud push fits the movie's spirit and helps an original film in a marketplace that does not exactly shower originals with support. He says he is 'leaving it on the field'—interviews, appearances, the whole circus, merch included.
He even pulled the Bob Dylan card to explain the mindset, basically: you are either pushing forward or fading out. He also made a point that his ambition is disciplined, not reckless. Looking back at early work like Call Me By Your Name and Beautiful Boy, he says the foundation is sturdier now, the artistry deeper, and when you are grinding 12-hour days there is not much room for self-doubt—just preparation and stamina.
- Title: Marty Supreme
- Director: Josh Safdie
- Writers: Ronald Bronstein, Josh Safdie
- Cast highlights: Timothee Chalamet, Gwyneth Paltrow, Odessa A'zion, Kevin O'Leary, Tyler Okonma
- Genre: Sports comedy drama
- IMDb: 7.6/10
- Release: Theaters nationwide on December 25
Is handing a power broker role to a power broker a genius move or playing with fire? My read: the private-plane story alone makes this worth the price of admission. Tell me where you land.