Surprising Reason Brad Pitt Didn’t Steal Matt Damon’s Role in Legendary $291M Leonardo DiCaprio Movie That Won 4 Oscars

Reviewed by: Barsha Dutta

Surprising Reason Brad Pitt Didn't Steal Matt Damon's Role in Legendary $291M Leonardo DiCaprio Movie That Won 4 Oscars

The Departed is a 2006 crime thriller film directed by Martin Scorsese. It has a fantastic story with so many twists and turns that will make your head spin. You’ll be guessing what’s going on until the very end, and chances are — you’ll probably get it wrong.

The Departed
The Departed

The movie is a remake of the 2002 Hong Kong film Infernal Affairs and takes inspiration from the real-life Boston Winter Hill Gang. The Departed won four Academy Awards and undoubtedly deserved more.

Leonardo DiCaprio and Matt Damon were perfectly cast for their roles in the film — it’s hard to imagine anyone more perfect for The Departed than them. But imagine how different The Departed would have been had Brad Pitt taken Matt Damon’s role in the film?

Also read: “That doesn’t turn me on”: Having S*x With Brad Pitt’s 54 Year Old Ex-Wife Was Insanely ‘Awkward’ for Jake Gyllenhaal in $17M Movie, Used the ‘Pillow Technique’ to Maintain Distance

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Brad Pitt Almost Took Over Matt Damon’s Role in The Departed

Matt Damon in the Departed
Matt Damon in The Departed

Brad Pitt initially intended to play the role of Colin Sullivan (played by Matt Damon later) opposite Leonardo DiCaprio‘s Billy Costigan. However, as the film continued to take shape, the age difference between the two actors became a concern.

Being a decade older than DiCaprio, Pitt felt it would be better if the characters were portrayed by younger men who were just starting their careers. Brad Pitt said to Interview Magazine:

“I thought I was too old for it.”

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.” 

So, Pitt stepped back from the role of Colin Sullivan but remained involved as a producer on the film. When The Departed was developing — he worked on Babel instead.

Although he couldn’t get cast with Leonardo DiCaprio in The Departed, he joined forces with DiCaprio in Quentin Tarantino’s Once Upon a Time in Hollywood.

Also read: “The…what was it? Shank, Sham, Shim?”: Morgan Freeman Blames $73M Iconic Movie’s Title for its Box-Office Failure That Was Turned Down by Tom Cruise and Brad Pitt 

Brad Pitt’s Role in Developing and Producing The Departed

Brad Pitt
Brad Pitt

The Departed would have never happened without Brad Pitt. Along with producing partner Brad Grey, Pitt originally bought the rights to Infernal Affairs and planned to star in the American adaptation.

Pitt and Grey secured William Monahan to write the script, and Monahan’s involvement got Martin Scorsese interested in the project. Pitt produced the film through his Plan B production company, although he ultimately didn’t appear.

Even though he didn’t win an Oscar for The Departed, he later earned an Academy Award for his work as a producer on 12 Years a Slave. He also won an acting Oscar for his supporting role in Quentin Tarantino’s Once Upon a Time in Hollywood.

Watch The Departed on Prime Video.

Also read: “I worked for a year on that one physically”: After Inspiring Many With ‘Fight Club’ Physique, Brad Pitt Went to Extreme Length to Show Up With a God Like Body Transformation in ‘Troy’

Source: Interview Magazine

Written by Shreya Jha

Shreya is naive, diurnal and a pop culture fanatic who serves as a celebrity news writer at Fandomwire.