Brad Pitt picks his favourite and most hated roles

Like many other struggling actors, Brad Pitt started his career with several uncredited roles, appearing in films such as No Way Out and No Man’s Land in the late-1980s. However, Pitt, harnessing refined acting skills and Hollywood looks, soon became one of the most prominent actors of the following decade, continuing his reign into the 21st century.

His small yet impactful performance in 1991’s Thelma and Louise helped to further establish the actor in the mainstream, leading to a role in Robert Redford’s A River Runs Through It and a memorable part in True Romance. By the mid-90s, Pitt was a certified star, appearing in movies such as Interview With the Vampire, Seven, Meet Joe Black and Fight Club.

Since the ’90s, Pitt has starred in numerous successful projects and even co-founded a production company in 2001, Plan B Entertainment, which has produced multiple Academy Award-winning movies, such as Moonlight and The Departed. The rise to acclaim was complete when Pitt won an Academy Award for ‘Best Supporting Actor’ in 2020 for his role as Cliff Booth in Once Upon A Time In Hollywood. 

Over the years, Pitt has reflected on his illustrious career, discussing the work he is most proud of and the roles he’d rather forget. During an interview with Newsweek, the actor shared his distaste for the 1997 thriller The Devil’s Own, in which he played an IRA member alongside Harrison Ford’s Irish-American police officer. Alan J. Pakula directed the movie, who previously helmed notable films such as To Kill A Mockingbird and Klute. He died the year after filming the movie, which received mixed reviews from critics. Regardless of its lukewarm reception, The Devil’s Own grossed $140million against a $90m budget, so it wasn’t a complete failure. 

Discussing the movie, Pitt explained: “We had no script. Well, we had a great script but it got tossed for various reasons. To have to make something up as you go along … what pressure! It was ridiculous. It was the most irresponsible bit of filmmaking – if you can even call it that – that I’ve ever seen.” 

Pitt also spoke out against Interview with the Vampire, which he claimed “frustrated” him. He explained to Rolling Stone: “I was disappointed with it. Because in the book, it was a guy trying to figure out who he was – if he’s a god or if he’s of the devil. The film focused more on the sensational antics of Lestat, which were done really well, but my character ended up getting dragged place to place and set up for the sensational moments. And it just became a little bit more whiny than a real search.”

However, Pitt hasn’t been all negative about his work. In an interview with GQ, he picked out his favourite project, which is, surprisingly, one of his least successful. “I can turn out the hits over and over, and I just, my favourite movie is the worst-performing film of anything I’ve done, The Assassination of Jesse James.”

The revisionist western was directed by Andrew Dominik in 2007 and featured a fitting score by Nick Cave and Warren Ellis. Despite receiving two Academy Award nominations for ‘Best Cinematography’ and ‘Best Supporting Actor’ for Casey Affleck, the movie only grossed $4m a the box office. Regardless, Pitt is a huge fan of the project, adding: “If I believe something is worthy, then I know it will be worthy in time to come.”

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