Matt Damon Replaced Brad Pitt In One Of The Best Crime Movies Of All Time

I remember sitting in the theater watching the opening scenes of Martin Scorsese's "The Departed" and thinking that it felt like a homecoming. "Bringing Out the Dead" and "The Aviator" had many fine qualities, but after those two and the hectic misfire of "Gangs of New York," I was yearning for some good old-fashioned Marty mob action. And here we were, on the mean streets of South Boston with the Rolling Stones grooving on the soundtrack and Jack Nicholson's Irish-American crime boss shaking down a shopkeeper for protection money. Everything felt right with the world. As the scene progresses, the villain hits on the guy's teenage daughter before loading up a kid with groceries out of respect for his family. That kid grows up to be Matt Damon in his most insidious role to date — but it was a part originally slated for Brad Pitt.

Damon plays Collin Sullivan, a lad who grows up under the wing of Frank Costello (Nicholson) before joining the Massachusetts State Police to act as a mole. Around the same time, Billy Costigan (Leonardo DiCaprio), another young man with a tough Boston upbringing, also graduates from the city's police academy. He is persuaded by Captain Queenan (Martin Sheenan) and foul-mouthed Sergeant Dignam (Mark Wahlberg) to go undercover and infiltrate Costello's organization. The cops know they have an informant in their midst and Costigan suffers severe mental strain from the constant fear of exposure, but which man will win the deadly game of cat and mouse?

"The Departed" is a remake of the acclaimed 2002 Hong Kong thriller "Infernal Affairs," but beyond the basic story beats, it feels like the kind of high-end crime epic that only Martin Scorsese makes anymore. It bears all his hallmarks as a master filmmaker and it was received incredibly well, becoming a box office hit and hailed by critics as an instant classic that ranks alongside the likes of "Taxi Driver," "Raging Bull," and "Goodfellas." It won Best Picture at the Oscars and also earned Scorsese his first and only Academy Award to date for Best Director. Brad Pitt was one of the producers of the film through his company, Plan B Entertainment, but why didn't he play Sullivan as originally intended?

Brad Pitt was riding high by the early 2000s after an Oscar nomination for his scene-stealing performance in "12 Monkeys" and starring in a string of hits including "Seven," "Fight Club," "Ocean's Eleven," and "Mr. & Mrs. Smith." (You also might have heard something about his high-profile relationship with his co-star in the latter, Angelina Jolie.) When he turned his attention to producing films in 2001, he proved that he also had a shrewd eye for picking a project, too. In 2003, he teamed with Brad Grey (a Plan B co-founder) and Warner Bros. to buy the rights to "Infernal Affairs," a film that is still regarded as one of Hong Kong's greatest crime movies.

With the story relocated to Boston and Martin Scorsese signing on to direct, it was announced in March 2004 that Leonardo DiCaprio and Pitt were set to star in the remake. Despite an unconvincing performance in "Gangs of New York," Scorsese kept faith with DiCaprio, transforming his career by casting him as Howard Hughes in "The Aviator" before lining him up for this role as nervy informant Billy Costigan. As for the other crucial part of Colin Sullivan, Pitt was soon replaced by Matt Damon. Damon told GQ how he was introduced to the project:

"We were shooting 'Ocean's 12' and Brad [Pitt] came up and said, 'Hey, want to be in a Martin Scorsese movie?' [...] Brad was gonna play either Leo's or my role, I can't remember which one. I guess they'd spoken to Marty and Marty was like, 'No, I'd like to have Matt.' I thought Brad was joking, I'm like, "What kind of actor do you ask that question of?' You know, I'm like, 'Shut up, man!' He's like, 'No, I'm actually serious," and he handed me the script and it was fantastic. I just felt like that was one of those things that fell from the sky."

Pitt himself may have been instrumental in Scorsese's decision to shoot for Matt Damon instead. Speaking to Interview Magazine in 2007, he recalled:

"Once [Martin 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. I thought I was too old for it."

Colin Sullivan in "The Departed" is a juicy role, and Brad Pitt deserves credit for stepping away from it. He is almost a decade older than Matt Damon, who himself was already 34 when cameras rolled. But Damon's boyish looks certainly help make the character seem more youthful, suiting the role of a ruthlessly ambitious young man who is prepared to do anything to put his tough upbringing far behind him. Sullivan is a fascinatingly amoral character, and the plot is driven by his ability to think on his feet and do some very bad things to cover his tracks. That's why I also think that the casting of Damon rather than Pitt was a masterstroke for the film.

Pitt made his big breakthrough playing a handsome hustler who woos Geena Davis in "Thelma & Louise," an eye-catching turn that might easily have seen him typecast in boring pretty-boy roles. Fully aware of that, Pitt quickly set about playing against type wherever possible: a hilarious small role as a sofa-bound stoner in True Romance," a serial killer in "Kalifornia," a kooky environmental terrorist in "12 Monkeys," and so on. He had also developed a bit of an edgy reputation offscreen too, with his well-documented weed habit and hanging out with Johnny Knoxville and the boys on "Jackass." To his colleagues, Sullivan is whiter-than-white, and Pitt's baggage and background of playing shady characters may have meant that it wouldn't come as such a surprise that he was capable of heinous acts to protect his identity as a mob mole.

It was far more of a shock to see Damon in the part of a dirty cop. Sure, he'd played a manipulative psychopath in "The Talented Mr. Ripley," but his squeaky-clean public persona made it especially queasy seeing him as a conniving killer masking his deception with his charm and sunny all-American looks. Arguably, Damon's chilling performance makes the movie, and it also made sense from the perspective of authenticity. Like fellow cast member Mark Wahlberg, Damon was born and raised in the Boston area and knows the accent and the city, something that contributed hugely to the flavor of the Oscar-winning "Good Will Hunting" screenplay that he co-wrote with Ben Affleck. Given Brad Pitt's reputation for dodgy accents, he certainly might not have been so convincing.