Why Brad Pitt Walked Away From a Martin Scorsese Role—Even After Helping Create The Departed

Brad Pitt may be one of Hollywood’s most enduring leading men, but even he has drawn the line when a role didn’t feel right. In a surprising twist of film history, the Oscar winner passed on the chance to star in Martin Scorsese’s The Departed—a film he not only helped bring to life, but which went on to win Best Picture.

The Producer Who Passed on the Spotlight

Pitt’s connection to The Departed runs deep. Through his production company, Plan B, he secured the rights to remake the Hong Kong crime thriller Infernal Affairs, bringing on screenwriter William Monahan to adapt the script. Scorsese didn’t join the project until after the screenplay was in place, but by then, Pitt was already considering a starring role—specifically, that of Colin Sullivan, the duplicitous cop later played by Matt Damon.

Why Pitt Said No

Despite being only seven years older than Damon, Pitt felt the character needed to be younger to truly sell the premise. Speaking to Interview, he explained:

“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. I thought I was too old for it.”

Rather than force a fit, Pitt stepped aside, opening the door for Damon to join Leonardo DiCaprio, Jack Nicholson, and Mark Wahlberg in the gritty Boston-set crime saga.

Sharing in the Success—Sort Of

While Pitt’s decision kept him off-screen, he still shared in the film’s success as a credited producer. The Departed became both a critical and commercial triumph, earning four Academy Awards—including Best Picture, Best Director for Scorsese, and Best Adapted Screenplay for Monahan.

However, there was a bittersweet twist: because Graham King was the sole producer recognized under the Academy’s rules, Pitt didn’t receive an Oscar statue for the Best Picture win, despite his instrumental role in developing the project.

The Sequel That Never Was

Though Scorsese dismissed the idea of a sequel, Mark Wahlberg later revealed that when he pitched a follow-up to Warner Bros., he floated both Pitt and Robert De Niro as potential new additions to the cast. The project never materialized, leaving Pitt permanently distanced from a property that, in many ways, began with him.

A Missed Opportunity or the Right Call?

For Pitt, the decision seemed rooted more in creative integrity than career calculation. By recognizing when a role wasn’t a natural fit, he avoided what could have been a jarring on-screen mismatch—while still shepherding one of the 21st century’s most acclaimed crime films to fruition.

In the end, The Departed marked a milestone for Scorsese and a triumph for Plan B, even if Brad Pitt never set foot in front of the camera.