The “fine-wine film” Brad Pitt wishes more people had seen: “It’s still labelled a loser”

Despite spending the last three decades as an ultra-successful leading man in a swathe of Hollywood’s finest films, Brad Pitt was once described by a director he twice worked with as a man afflicted with “congenital sadness”.

When Aussie filmmaker Andrew Dominik spoke about directing the first film to emerge from Pitt’s production company Plan B, he indicated that the actor created the company specifically because he “has mixed feelings about the films that made him famous”.

The likes of Legends of the Fall, Meet Joe Black, and Interview with the Vampire have never sat well with Pitt, a melancholy soul who hated being pushed into the kinds of films that put his good looks front and centre.

A quick look at the list of movies produced by Plan B that Pitt also decided to star in backs up Dominik’s claim perfectly. There is Terence Malick’s elegiac The Tree of Life, Bennett Miller’s low-key sports drama Moneyball, Steve McQueen’s searing 12 Years a Slave, and James Gray’s depressing sci-fi drama Ad Astra, or, as many took to calling it, ‘Sad Bradstra’. Most of these films weren’t exactly big earners for Pitt at the box office, but they’re also undeniable shoo-ins for any list of his greatest films.

According to the actor, though, the first movie he made with Dominik may still be his favourite film he has ever starred in, despite The Assassination of Jesse James by the Coward Robert Ford also being one of his biggest box office flops. The three-hour western amassed a truly horrifying $3.9million at the US box office, as well as a scant $11m around the world.

This $15m total was only half of what Warner Bros paid to make the film, and that’s without taking into account the extra millions the studio paid for marketing. It was a chastening result, although Dominik later indicated that everyone involved had a feeling the slow-paced, poetic, plot-light film was always going to be a tough sell, or, as he eloquently put it, “We knew this thing was gonna fuckin’ tank”.

Over the years, Jesse James has developed a cult following and is now viewed as one of Pitt’s best films, but at the time, he lamented how it was “labelled a loser”. While he recognised exactly why a studio would think that way (“To their credit, they put $40million into that movie, and they made nothing, so I understand their disdain”), the movie’s box-office flameout never changed how he felt about it. “I love that film,” he told Entertainment Weekly, “I find it lyrical and poetic and under the surface”.

In truth, The Assassination of Jesse James by the Coward Robert Ford (a lengthy title Pitt insisted in his contract that the studio couldn’t alter) is the quintessential ‘sad Brad’ film. Everything that Warner was afraid of, from its meandering pace, sorrowful tone, sombre cinematography, and morally murky conclusion, was precisely what the actor loved about the project. In the end, he got the make the movie exactly how he wanted, and even when Dominik “couldn’t get a job for several years afterward” because of its nuclear reputation, Pitt stuck by him.

Ultimately, he championed Dominik’s next directorial effort, 2012’s financial crisis noir Killing Them Softly, which gave Pitt another of his best roles as the pompadoured, philosophical hitman Jackie Cogan. He also never let Dominik forget how highly he thought of Jesse James, often telling the filmmaker, “That one’s a fine-wine film. It’s gonna age well”.

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