From Esquire: “Lamp-lit figures emerge from the woods. A train rounds a corner. Illuminated among the undergrowth are men with sacks covering their faces, rough eye holes cut out, shotguns cradled in their arms. There is a hiss of steam and sparks as the train slows. Guns popping, the bandits emerge, intent on robbery. Pitt’s Jesse James swaggers among them, cool and in command. This is one of the best, one of the most eerie and menacing and beautiful scenes in the best film of Brad Pitt’s career.

Pitt was 42 years old during the filming of The Assassination of Jesse James by the Coward Robert Ford and perhaps the biggest movie star in the world. In 1999 Fight Club had turned the Oklahoma native red-hot. The rebooted Ocean’s Eleven cemented his leading man status. The perfect time, then, to take a left turn into a low budget, ponderous historical epic meditating on the celebrity culture Pitt embodied, through the lens of the life and death of a late 19th-century train robber.

The Assassination of Jesse James… was intended to be “a dark, contemplative examination of fame and infamy,” the film’s director, Andrew Dominik said in an LA Times article. Dominik succeeded in that, while showing us a side of Pitt of which we arguably haven’t seen enough. As James, Pitt is introspective, mournful, exhausted, quick to anger, compassionate, ruthless, yet kind. Observe how in the final scene, with acceptance etched on his face, he watches his children play, sets down his gun belt, then turns his back to accept the bullet from Casey Affleck’s assassin. It’s a career-best performance in a career best film.

Unfortunately, these types of performances aren’t always assured. There are two sides to Pitt the actor. For every goofy stoner/bro character (True Romance, Burn After Reading, War Machine) there’s the artist, the auteur, the Pitt whose characters we imagine dabble in sculpture and study German architecture in their spare time, just like Pitt himself. Which isn’t to say the more comedic performances aren’t good, just that when Pitt digs deeper he’s able to convey more of the human experience, for a deeper, more fleshed-out piece of work. When he embraces this, in films like Moneyball, The Tree of Life, Ad Astra and, especially, Jesse James, Pitt is never better.

Moving away from the lighter stuff into more weighty material was a conscious decision. “In the ’90s I did become aware that there was this kind of leading-man role that you could plug any of us into and it didn’t even matter,” Pitt told the New York Times in 2019. “We would all have the same result.” He’s right. Is popcorn fare like Mr & Mrs Smith, Snatch, or The Mexican elevated by having Pitt in it? Yes, sure. But would it make a huge difference if Tom Cruise or Matthew McConaughey or Val Kilmer or whoever had taken these roles instead? Probably not.

Pitt points to the 2004 flop Troy as the moment he decided to invest in solid, meaningful stories. As a producer, this shift saw him back Oscar-winning projects including The Departed, 12 Years A Slave, and Moonlight. As an actor, he’s been nominated for four Oscars, eventually winning one in 2020. “I was a pretty good actor before, but definitely hit and miss. I think I became a really good actor,” Pitt told The Telegraph in 2015.

Of course, it takes more than serious performances in serious films to make a good actor. The Angelina Jolie-directed By The Sea is weighed down to the very bottom of the ocean by its own self-importance. And the Cormac McCar-hy-penned The Counsellor could not be saved even by the combined talents of Ridley Scott and one of the best movie casts ever assembled.

There is a sweet spot between weighty and comedic in Pitt’s two Tarantino-directed outings, Inglourious Basterds, and Once Upon A Time In Hollywood. But even then, in Pitt’s Oscar-winning performance in Once Upon A Time… he’s largely playing the straight guy to Leonardo DiCaprio’s larger-than-life film star (acid-dipped cigarettes aside).

Arguably, despite his many hits, Pitt has never recaptured the perfect storm of filmmaking that went into Jesse James. His performance, Roger Deakins’ cinematography, the set design, Nick Cave and Warren Ellis’s soundtrack, the editing, Dominik’s direction, and supporting performances from Sam Shepard, Sam Rockwell, and Mary-Louise Parker all tie together to make this the finest film of Pitt’s career – and one that he is yet to better, 15 years later.

While the forthcoming Bullet Train seems to find Pitt slipping back into blockbuster-bro mode, let’s hope we get at least one more ambitious epic on the scale of Jesse James before the 58-year-old actor hangs up his gun belt for good.”