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Which Oscar-winning movie did Hollywood stars Brad Pitt and Leonardo DiCaprio turn down?

The ‘Once Upon a Time in Hollywood’ actors could have lined up alongside one another in another groundbreaking film years earlier.

Which Oscar-winning movie did Hollywood stars Brad Pitt and Leonardo DiCaprio turn down?
FABRIZIO BENSCHREUTERS

Brad Pitt and Leonardo DiCaprio need no introduction. The pair have become two of Hollywood’s biggest and best-known stars, and have been recognised for their work on a whole host of movies, with the former having won two Academy Awards to the latter’s one (Pitt is 11 years older, so there’s still time for DiCaprio to catch up). The actors have done pretty well for themselves, even lining up together in Quentin Tarantino’s critically acclaimed Once Upon a Time in Hollywood, but even the best make mistakes from time to time. And it turns out Pitt and Di Caprio made the exact same one.

The tale begins at the start of the millennium, when film director Gus Van Sant was planning to make his next movie and hoped to line up an all-star cast, including two male leads. Van Sant originally considered casting Matt Damon and Joaquín Pheonix, although Pitt and DiCaprio were also an option. The latter pair received copies of the script but ended up turning down their respective roles.

Brad Pitt at the Formula One British Grand Prix in July.
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Brad Pitt at the Formula One British Grand Prix in July. ANDREJ ISAKOVICAFP

Why did Pitt and Di Caprio turn down Brokeback Mountain?

Van Sant ultimately didn’t make the Brokeback Mountain, which was nevertheless released in 2005 after Taiwanese filmmaker Ang Lee took it up. The neo-Western romantic drama proved to be a huge success at the box office, with the never-before-told story of homosexual cowboys lauded as a landmark in LGBT cinema.

Damon ruled himself out the running as he had previously played a gay man in The Talented Mr. Ripley and a cowboy in All the Pretty Horses. “I can’t follow it up with a gay cowboy movie!” the actor told Van Sant. In a later interview, however, Damon admitted he had made the wrong decision. Josh Hartnett was also approached but dropped out due to scheduling conflicts.

Pitt and DiCaprio reportedly struggled to see themselves playing the required roles, unaware of the movie’s - and the main characters’ - potential to break ground. Anne Hathaway, Michelle Williams and Anna Faris joined the cast before promising young twenty-somethings Heath Ledger and Jake Gyllenhaal were confirmed for the lead roles.

Leonardo DiCaprio was recently spotted at the US Open tennis men's singles final between Daniil Medvedev and Novak Djokovic.
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Leonardo DiCaprio was recently spotted at the US Open tennis men's singles final between Daniil Medvedev and Novak Djokovic. SARAH STIERAFP

How many Oscars was Brokeback Mountain nominated for? How many did it win?

The movie received eight Oscar nominations in 2006, with Ledger up for Best Actor and Gyllenhaal for Best Supporting Actor. Neither ultimately won, but Lee went home with the Best Director award and Brokeback Mountain won three Academy Awards in total.

The one that got away for Pitt and Di Caprio.