The huge Matt Damon roles that Brad Pitt turned down
Very few Hollywood A-listers can claim to have been a pin-up of such artistic substance and cinematic zeal as Brad Pitt. The acclaimed actor and producer has deftly combined a magnetic on-screen presence with versatile acting talent, bringing life to modern classics like Fight Club, The Curious Case of Benjamin Button, Ocean’s Eleven and Inglourious Basterds. While acting was always Pitt’s biggest passion, he aimed to work both sides of the camera from a young age.
In 1986, a 22-year-old Pitt spoke to Tiger Beat for one of his earliest interviews. “In ten years, I’ll be 32,” Pitt pointed out. “I hope I am married with some Brad Jrs. I would like to be in a position like Kevin Costner. He’s on top and respected as an actor. I just want to be a respected actor. I want to make people feel things like how I feel when I go to the movies. I would like to have my own production company.”
By 1996, Pitt had succeeded beyond his wildest conception with innumerable roles in highly acclaimed and commercially seismic movies. Remembering his youthful dreams, Pitt co-founded Plan B Entertainment with Brad Grey, Kristin Hahn and Jennifer Aniston in 2001 and has since become a prolific producer.
Looking back, Pitt has very few decisions to lament. However, if he was pushed to dig up any career regrets, there were several projects he might regret taking and that he might regret not taking. Pitt famously tried to back out of his role in Neil Jordan’s Interview with the Vampire after reading the script, but the movies he missed out on are a little harder to detect.
As it happens, two of Pitt’s most colossal missed opportunities are roles that later landed on his Ocean’s Eleven co-star Matt Damon. Before the young Oscar-winner clinched the lead in Doug Liman’s 2002 Robert Ludlum action novel adaptation, The Bourne Identity, Pitt was offered the role. Pitt would have taken on the job, but at the time, he was signed on to star in Tony Scott’s Spy Game and had to decline due to contractual obligations.
In 2003, Pitt and the Warner Bros producer Brad Grey purchased the rights to remake an American version of the Hong Kong police thriller Internal Affairs. Initially, they intended for Pitt to star as the Boston police officer Colin Sullivan opposite Leonardo DiCaprio’s William Costigan.
Ultimately, this project would be titled The Departed under Martin Scorsese’s capable direction. Pitt revealed why he let the role go in a 2007 interview with Interview Magazine, “I thought it would be better if [the leads] were younger guys that were just starting their lives, guys coming out of the academy, guys who were hungry. I thought I was too old for it.”
Whether or not Pitt was too old for the role is up for debate, but few can fault Matt Damon’s embrace of the central position in what became one of the 2000s’ most acclaimed productions. Watch the trailer for The Departed below.
