Brad Pitt's Near Miss with a Major Role in 'The Departed'

In a fascinating twist of fate, Brad Pitt and Leonardo DiCaprio could have shared the screen 13 years before their collaboration in "Once Upon a Time… in Hollywood." However, Pitt turned down a significant role in Martin Scorsese's acclaimed film, "The Departed," for a compelling reason.

The long-awaited pairing of these two stars finally occurred in Quentin Tarantino's 2019 film, but it could have happened much earlier under the direction of Scorsese. The backstory reveals that Pitt was not merely a potential actor; he was instrumental in the film's development.

Pitt's Involvement in the Project

The journey began in 2003 when Brad Pitt, alongside Warner Bros. and producer Brad Grey, secured the rights to adapt the Hong Kong thriller "Infernal Affairs." As the project evolved, screenwriter William Monahan was brought on board, and Scorsese eventually joined the team. Initially, the plan was to cast both Pitt and DiCaprio in the lead roles.

However, Pitt later reconsidered his involvement. He believed that the story would resonate more with younger actors who could authentically portray characters at the early stages of their careers. In a 2007 interview with Interview magazine, he explained, “I developed it for two and a half years. We fought for this film, and then we got William Monahan to write the script. Once [Martin] Scorsese got involved, I thought it would be better if it were younger guys starting out, guys who are hungry. I thought I was too old for that.”

Matt Damon Steps In

Ultimately, Pitt stepped aside from the role but remained on board as a producer. Matt Damon was then cast as Colin Sullivan, opposite DiCaprio's character. In "The Departed," the two actors find themselves on opposing sides of the law: Billy Costigan (DiCaprio), a young cop with a troubled past, goes undercover in the Boston mafia, while Sullivan (Damon) is a promising officer secretly working for mob boss Frank Costello, played by Jack Nicholson.

Warner Bros. Pictures

Despite Pitt's absence, the film went on to achieve remarkable success. Released in 2006, "The Departed" not only won critical acclaim but also earned Scorsese his long-awaited Oscar for Best Director, alongside awards for Best Picture, Best Adapted Screenplay, and Best Film Editing.

Pitt's Alternate Path

While DiCaprio and Damon were working with Scorsese, Pitt chose to pursue a different project. In 2006, he starred in "Babel," directed by Alejandro González Iñárritu, alongside Cate Blanchett. This decision proved fruitful, as Pitt received a Golden Globe nomination for Best Supporting Actor for his performance.

Years later, the paths of Pitt, DiCaprio, and Scorsese would intersect again in an unexpected manner. In 2015, all three appeared in "The Audition," a short film directed by Scorsese, although it was not the anticipated feature that fans had hoped would unite Pitt and DiCaprio.

The Long-Awaited Collaboration

The long-anticipated collaboration finally materialized in 2019 with Tarantino's "Once Upon a Time… in Hollywood." In this film, DiCaprio plays Rick Dalton, an actor facing a career decline, while Pitt portrays Cliff Booth, his loyal stunt double. Their pairing became a central selling point for the film, which garnered ten Oscar nominations and won two, including Best Supporting Actor for Pitt.

Sony Pictures Releasing

It took over a decade for Pitt and DiCaprio to share the screen in a full-length feature, and while Pitt has never publicly expressed regret for passing on his role in "The Departed," his decision ultimately allowed Scorsese to assemble the iconic cast that defined the film.

For those interested in revisiting these films, "The Departed" is currently available for streaming on Sooner, while "Once Upon a Time… in Hollywood" can be accessed on Prime Video and HBO Max.