The role Brad Pitt thought he was “too old” for

Making an absolute mockery of the concept of ageing, Brad Pitt is now in his 60s and shows no signs of succumbing to the inevitable ravages of time. However, his advancing years did lead to the star ruling himself out of the running for a major hit.

The actor has never worked directly with Martin Scorsese in an on-camera capacity, but he was nonetheless integral to the success of The Departed. It was Pitt who initially purchased the rights to mount a remake of Hong Kong favourite Infernal Affairs through his Plan B production company, with William Monahan boarding the project as screenwriter.

Scorsese didn’t come aboard until after the script had been written, but by the time The Departed went into production, Pitt didn’t think he was the right fit for the ensemble. During the earliest stages of development, it was widely reported that he’d be playing Colin Sullivan opposite Leonardo DiCaprio’s Billy Costigan before Matt Damon was eventually hired instead.

Even though there’s only a seven-year age difference between the two Ocean’s co-stars, Pitt felt he was a touch too grizzled to convince as a corrupt police officer who was fresh out of the academy. As he explained to Interview, he was happy to step aside in favour of a more youthful-looking performer.

“Once Scorsese became involved, I thought it would be better if they were younger guys that were just starting their lives, guys coming out of the academy, guys who were hungry,” he said. “I thought I was too old for it.” Having declined the chance to collaborate with Scorsese, Pitt missed out on The Departed‘s on-screen success but shared in the spoils regardless.

The downside is that even though Pitt was the originator of the project and was credited as a producer, he wasn’t presented with an Academy Award when the film won ‘Best Picture’, with Graham King the sole recipient of the most prestigious prize cinema has to offer.

Scorsese would finally snag that elusive ‘Best Director’ award, too, while Monahan – who was hired by Pitt’s Plan B to pen the adaptation in the first place – took home the trophy for ‘Best Adapted Screenplay’. The Departed wouldn’t have happened in the way that it did without his involvement in its formative stages, but Pitt didn’t seem too disheartened by his decision not to star.

Its director may have baulked at the mere suggestion of The Departed becoming a franchise, but Mark Wahlberg admitted that when he went to Warner Bros to pitch a sequel, he suggested both Pitt and Robert De Niro as potential co-stars. It didn’t end up happening at all, keeping the A-lister at a permanent arm’s length from a property that wouldn’t have existed in its current form to begin with were it not for him.

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