The iconic Martin Scorsese role that Brad Pitt rejected: “I was too old”
We are yet to see Brad Pitt star in a Martin Scorsese movie, and that’s a crying shame.
Yet, it should also be noted that it’s hard to imagine anyone more perfect for The Departed than Leonardo DiCaprio and Matt Damon. The two A-list actors were highly acclaimed in Martin Scorsese’s remake of the 2002 Hong Kong thriller Infernal Affairs, playing off each other with equal parts youthful exuberance and paranoid visions.
As mirror images of two sides of the law, DiCaprio and Damon battle it out while never actually coming face to face until the final act of a film that weaves crime conspiracies into a gripping web. But that showdown could have looked a lot different, considering that Brad Pitt was originally going to take Damon’s role.
In fact, The Departed would never have happened without Pitt being involved in the first place. Along with producing partner Brad Grey, Pitt originally bought the rights to Infernal Affairs and intended to star in the American remake. Pitt and Grey secured William Monahan to write the script, and it was Monahan’s involvement that got Scorsese interested in the project.
Monahan had previously penned Kingdom of Heaven and garnered plaudits for his work. He’d also been a novelist compared to Kingsley Amis before venturing over to screenplays, and Scorsese must’ve been fond of his work.
“I developed that for two and a half years,” Pitt revealed in a 2007 feature in Interview Magazine. “We fought for that movie, and then we got William Monahan on the script.” During these initial stages, it was imagined that Pitt would still play the nefarious Boston mob rat Colin Sullivan opposite DiCaprio’s Massachusetts State Police mole Billy Costigan.
Sullivan and Costigan are two sides of the same coin: intelligent young men who look to rise above their circumstances by any means necessary. Their approaches are uncannily similar, with both men hiding their insecurities and uncertainties with a steely Irish exterior. The only thing that separates them is which side they find themselves on.
Sullivan is recruited into mob boss Frank Costello’s crew at a young age, while Costigan’s father couldn’t be bought by the feared gangster. The reputation of Costigan’s family in the Irish mob is solid enough for him to infiltrate Costello’s gang while reporting back to the “staties”, but in the process, Costigan begins to dramatically, chillingly unravel.
As The Departed continued to be developed, a fairly obvious issue came up: Pitt was a full decade older than DiCaprio. While Pitt has a remarkable ability to look younger than his six decades on earth, the one person who couldn’t reconcile the age difference was Pitt himself.
“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,” Pitt explained in the same interview. “I thought I was too old for it.” Given how much of a fan Pitt is of Scorsese’s work, that’s a sign of his dedication to the integrity of the movies he produces. So, he simply winced and rejected the role.
Pitt continued his work on the film as a producer, although he didn’t take home an Oscar when the film won ‘Best Picture’ at the 79th Academy Awards. He would have to wait until 2014 to take home his first Oscar as a producer of 12 Years a Slave. Pitt hasn’t had a chance to star in another Scorsese film, but he did finally win an acting Oscar for his supporting role in Quentin Tarantino’s Once Upon a Time in Hollywood.
Will he ever star in one of the Il Maestro’s movies? Well, while Scorsese certainly isn’t slowing down even well into his 80s, Pitt himself has given muted suggestions that he might soon retire. All we know is it would almost certainly be a classic.
