Brad Pitt Almost Starred in a Top 2000s Thriller—Here’s Why He Passed!

It wasn’t until 2019 and Quentin Tarantino’s Once Upon a Time… in Hollywood that Brad Pitt and Leonardo DiCaprio truly shared the screen in a feature film. However, this collaboration could have occurred thirteen years earlier under the direction of Martin Scorsese.

Interestingly, Brad Pitt was not just considered for a role; he was actively involved in the initial stages of the project. The film in question was none other than The Departed, which became one of Scorsese’s major hits and a defining crime film of the 2000s.

Brad Pitt, the Driving Force Behind the Project

The journey began in 2003. Along with Warner Bros. and producer Brad Grey, Brad Pitt acquired the rights to adapt the Hong Kong thriller Infernal Affairs, which had been released the previous year.

The project gradually took shape, and William Monahan was brought on board to write the screenplay. When Martin Scorsese finally joined the project, the original idea was to cast Brad Pitt and Leonardo DiCaprio as the two central characters.

However, Pitt eventually reconsidered his role in front of the camera. He felt that the story worked better with younger actors portraying these men at the beginning of their careers. He explained his reasoning in a 2007 interview with Interview Magazine:

“I developed it for two and a half years. We fought for this film, and then we got William Monahan to [write] the screenplay. Once [Martin] Scorsese got involved, I thought it would be better with young guys starting out, guys fresh out of the academy, guys who are hungry. I thought I was too old for that.”

Matt Damon Ends Up Taking the Role

Brad Pitt ultimately decided not to act in the film, although he stayed on as a producer. It was Matt Damon who ended up playing the role of Colin Sullivan opposite Leonardo DiCaprio.

In The Departed, the two men operate on opposite sides of the law. Billy Costigan (Leonardo DiCaprio), a young cop with a troubled past, goes undercover in the heart of Boston’s mafia. His mission: to get close to Frank Costello, the formidable mob boss played by Jack Nicholson.

Meanwhile, Colin Sullivan (Matt Damon) has a promising career in the police department but secretly works for Costello. Two moles find themselves on opposing sides, each trying to uncover the other’s identity before their own cover is blown.

Brad Pitt’s decision did not prevent the film from achieving remarkable success. Released in 2006, the thriller earned Martin Scorsese his long-awaited Oscar for Best Director. The film also won awards for Best Picture, Best Adapted Screenplay, and Best Editing.

Brad Pitt Chooses a Different Path

While Leonardo DiCaprio and Matt Damon were filming with Scorsese, Brad Pitt chose a different direction. In 2006, he starred in Babel, directed by Alejandro González Iñárritu, alongside Cate Blanchett.

This decision proved to be quite successful: his performance in the film earned him a Golden Globe nomination for Best Supporting Actor.

The paths of Pitt, DiCaprio, and Scorsese would cross again a few years later in an unexpected way. In 2015, the three stars participated in The Audition, a short promotional film directed by Scorsese. However, it was not the major film featuring Pitt and DiCaprio that some might have hoped for.

It Took Tarantino to Truly Bring Them Together

The on-screen meeting finally occurred in 2019 thanks to Quentin Tarantino. In Once Upon a Time… in Hollywood, Leonardo DiCaprio plays Rick Dalton, an actor whose career is on the decline, while Brad Pitt plays Cliff Booth, his stunt double and loyal friend.

Thirteen years after the missed opportunity with Scorsese, their collaboration became one of the main selling points of the project. The film was a hit, earning ten Oscar nominations and winning two awards. Brad Pitt notably won the award for Best Supporting Actor for his portrayal of Cliff Booth.

It took more than a decade for the two actors to finally star together in a significant film. And while Brad Pitt has never publicly regretted letting Matt Damon take his place in The Departed, his refusal ultimately contributed to giving Scorsese’s masterpiece the cast it is known for today.

To (re)discover these two films, The Departed is currently available for streaming on Sooner, while Once Upon a Time… in Hollywood is accessible on Prime Video and HBO Max.

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