Brad Pitt Has Been Cool For Three Decades Now. How Does He Do It?

Quentin Tarantino’s latest movie, Once Upon a Time… in Hollywood, just had its world premiere. And while the plot partially follows real-life Manson victim Sharon Tate (Margot Robbie), the movie is really a showcase for its two male leads: Leonardo DiCaprio and Brad Pitt. The film’s premiere was preceded by a lengthy profile of DiCaprio in The Hollywood Reporter which essentially posited that he is the greatest working actor of his generation. But Once Upon a Time… in Hollywood also helps cement what we’ve known to be true for years now: Brad Pitt is one of the most charismatic human beings alive.

Pitt’s first memorable appearance on-screen was as the young cowboy in 1991’s Thelma & Louise, a role which, together with romantic drama Legends of the Fall a few years later, helped him on the path to becoming a Nineties sex symbol. But even back then, Pitt was more than just a pretty boy: as Louis in the 1994 baroque horror Interview with the Vampire, he held his own performance-wise against Tom Cruise, who had been leading movies for almost a decade at that point.

Looking back, it was perhaps unavoidable that Pitt would become one of the most in-demand actor of his time. He looked like a young Robert Redford, and had the innate coolness of Steve McQueen (not to mention a likeable, swaggering, slightly cocky quality that would probably be identified as big dick energy today). And his output over the next ten years proved that he had the acting chops to go with the movie star persona: Seven, 12 Monkeys, Sleepers, The Devil’s Own, Seven Years in Tibet and Meet Joe Black were all huge hits, and a number of them remain cult faves to this day.

And then came the movie that propelled him to even greater heights: 1999’s Fight Club. It was the perfect storm: a darkly comical satirical script that gave Pitt the chance to take his natural charm to a darker place and cut loose with a character that literally embodied the worst human impulses… and those abs. 20 years later, Tyler Durden is still one of the most gleefully destructive characters in pop culture.

And ever since, Pitt’s presence in a movie has been all but guaranteed to sell tickets, whether it’s backing up George Clooney in Ocean’s Eleven, donning a sword and sandals in Troy, ageing backwards in The Curious Case of Benjamin Button, or (somehow) making math cool in Moneyball. He’s also used his clout to help lesser known filmmakers get their projects made: he produced both Selma and Moonlight.

At the recent Once Upon a Time… in Hollywood premiere, Pitt, 55, said that he has no plans to retire any time soon, although he did say that acting is, overall, “a younger man’s game.” But if he did want to age gracefully into another phase of his acting career à la Robert Redford or Sam Elliott, he’d probably look damn good doing it.

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