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Superstar Brad Pitt received his first Oscar earlier this year. After nominations for 12 Monkeys, The Curious Case for Benjamin Button, and Moneyball, the actor finally brought home the gold for his role in Once Upon A Time in Hollywood.

Eschewing the “leading man” persona he gained early in his career, Pitt was never thrilled with being typecast. A former co-star once commented on Pitt’s talent being overlooked by his Hollywood persona.

Brad Pitt poses with the trophy for Outstanding Performance by a Male Actor in a Supporting Role in the press room during the 26th Annual Screen Actors Guild Awards
Brad Pitt | JEAN-BAPTISTE LACROIX/AFP via Getty Images

Brad Pitt’s star rises in the 90s

After his star-making role in the 1991 film Thelma & Louise, Pitt landed leading parts in Interview with the Vampire, Legends of the Fall, and Se7en. Gracing the covers of countless tabloids, the Academy Award winner alluded to feeling stereotyped at the time.

“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,” he told The New York Times in December. “We would all have the same result.” 

Pitt revealed he made a conscious choice to seek out projects of substance after starring in the commercial epic Troy in 2004.

“As I’ve gotten older, I’ve become more conscious of thinking, If I am the one to play something, what can I bring that’s unique?” the Ad Astra star shared. “I made a decision [after Troy] that I was only going to invest in quality stories, for lack of a better term. It was a distinct shift that led to the next decade of films.”

Streaming may be in Brad Pitt’s future

The Fight Club star is concentrating on projects offscreen through his Plan B production company. Pitt noted how Hollywood tends to gravitate toward a youthful demographic rather than his mid-50’s age group.

“I’m behind the camera on the producing side and I enjoy that a lot,” the Babel actor told GQ Australia in July 2019. “But I keep doing less and less. I really believe that overall it’s a younger man’s game – not that there aren’t substantial parts for older characters – I just feel, the game itself, it’ll move on naturally.”

Noting the rise of opportunities on streaming platforms like Netflix and Amazon Prime, Pitt isn’t counting himself out of show business just yet.

“I’m curious to see what the future of film is, what shape it takes. I really appreciate the streaming services because we’re seeing more and more quality projects being made,” he said. “It just tells you how many talented people are out there. I like to think there’s room for both. But I could be a dinosaur and not even know it, man.”

High praise from one Oscar winner to another

Pitt has starred alongside some of Hollywood’s most legendary actors including Robert Redford and Morgan Freeman. Teaming up with Academy Award winner Anthony Hopkins for Legends of the Fall in 1994 and Meet Joe Black in 1998, Pitt still shares a bond with the veteran actor. The two met in December to discuss their careers and the film industry.

“As actors, what we do is a team sport. Making a film takes everyone,” Pitt told Hopkins in a conversation for Interview. “And we contribute what we contribute. Sometimes it’s going to be better than what we gave on the day. Sometimes it’s weaker than what we gave on the day. But it’s a team effort.”

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The Silence of the Lambs star agreed while putting their jobs in perspective. “It’s important to do it for the passion, the sheer enjoyment, the life force, but to not take it too seriously,” Hopkins noted.

Getting to know Pitt over the years, Hopkins called him “a character actor in a matinee idol’s body.” The praise wasn’t lost on the Allied star. “It was the greatest compliment I ever received,” Pitt revealed, according to the Telegraph.

The divorced father of six pinpointed when he began to notice a distinct change in his work. “I was a pretty good actor before, but definitely hit and miss,” Pitt remarked. “I think I became a really good actor. I’m sure a lot of that has to do with age and wisdom too. But I see an absolute shift from the day I started my family.”