'The Mastermind' Review: A Brilliantly Bleak Comedy of Failure
- Alex Gilston
- Oct 17
- 4 min read
Updated: Oct 29
By Alex Gilston - October 17, 2025
The Mastermind is puzzling. It advertises itself as a romp-heist film with an elaborate crime and an even more elaborate plan to commit it. Kelly Reichardt, however, pulls us in under these pretences and then pulls the rug from beneath us with something different. The unravelling of one man with enough ego to convince himself that he might succeed, instead, though his remarkable failure becomes the blueprint of Reichardt’s exploration. It won’t be for everyone, but The Mastermind is an interesting cinematic achievement for Kelly Reichardt.
It is the 1970s, and James Mooney (Josh O’Connor, in his second of three films at the London Film Festival this year) is casing his local art gallery, hoping he can pull off a heist, stealing several paintings. James has a family, and it becomes clear he’s struggling to provide for them. The heist for him is a way out, giving him comfort from the money he might make from the paintings. Reichardt uses her signature brand of slow-moving direction, slowly transporting us through the motions up until the heist. James’ plans are far from smooth, however, as one of his collaborators drops out at the last minute, and he is forced to find a replacement. This is a sign of things to come as they travel towards the gallery to commit the theft.
Interestingly, the heist is the only moment in the film that feels anywhere near a brisk pace. The title of The Mastermind would have you believe that James is an expert, but as we see the robbery play out, the realization dawns that he is a complete amateur who has thrown the plan together with string and tape. The masks they use are women’s stockings; they stuff the paintings into burlap sacks and do the whole thing in broad daylight. But James and his accomplices end up escaping with the paintings, and the first domino falls as Ronnie pulls a gun on the security guard.
The heist is done, and the brakes are slammed as The Mastermind comes into its own. James’ pathetic nature is further exemplified by his hiding the paintings at his farmstead. It takes James about ten minutes as he struggles to carry each of the three paintings up a ladder individually, and then the box they were in. It is a clever use of Reichardt’s film style to highlight his ineptitude. In the morning, though, he gets a visit from the police, who ask him questions about the crime. Even though they leave without arresting him, his wife, Terri (Alana Haim), has seen enough to leave the house with their kids. James’ ego is his downfall, as something he thought he was doing to make a better life for his family is now why they are leaving him. If it isn’t plainly obvious to the police that James has committed this crime, it becomes so when Ronnie holds up a local bank, gets arrested, and instead of facing the consequences of his action, he attempts to go on the run.
Reichardt masterfully moulds her exploration of masculinity and ego as James tries to move states to evade capture. He finds himself at his friend Fred’s (John Magaro) house. He and his partner Maude (Gabby Hoffman) help him out of the goodness of their hearts, but it’s a true distillation of how James’ ego has blinded him, not realizing that even just his being there could implicate them in the crime as well.
There’s a bleak nature to James being consistently beaten down without any respite on the horizon, but it continues until he reaches a breaking point. With no money to get any further, James resorts to mugging an old lady. But it isn’t this that is his ultimate downfall. Frantic and on the run from this crime, he stumbles into a protest against army conscription, where he is arrested, not for the mugging but for being a part of the protest. It’s the final nail in the coffin in his bleak comedy of errors, losing everything he had in the process. It’s not the happiest ending, but sometimes in cinema it’s nice to go down a different path, one where the oaf you’re following doesn’t get what he wants.
Is The Mastermind Worth Watching?
In The Mastermind, Kelly Reichardt once again proves her unmatched ability to find meaning in the mundane and poetry in failure. What begins as a clever setup for a crime caper transforms into a meditation on masculinity, delusion, and the quiet tragedy of unrealised ambition. Josh O’Connor delivers a painfully compelling performance as James, a man who mistakes desperation for genius, and whose downfall feels both inevitable and oddly human.
The Mastermind is released in cinemas on October 24
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