"I Was Too Old for it”. 13 Years before Tarantino's Film, Brad Pitt Turned Down a Role alongside Leonardo DiCaprio

As a die-hard movie buff with decades of cinematic experiences under my belt, I can’t help but feel a pang of regret that Brad Pitt and Leonardo DiCaprio didn’t share the screen earlier than they did in “Once Upon a Time in Hollywood.” Their potential pairing in “The Departed” would have been a masterclass in acting prowess, a perfect storm of talent that could have left audiences breathless.


Brad Pitt and Leonardo DiCaprio are undeniably two of the most prominent figures in Hollywood, with their presence in a movie’s cast often ensuring its box office success. Remarkably, these two actors nearly collaborated 13 years ago on Martin Scorsese’s film “The Departed.” However, they actually met for the first time during the production of Quentin Tarantino’s Academy Award-winning movie, “Once Upon a Time in Hollywood.”

2003 saw Brad Pitt purchasing the rights to remake the Chinese film “Infernal Affairs.” Initially, it was intended for him and Leonardo DiCaprio to star in the leads. However, Pitt declined the role, expressing that he felt himself being “too old” for it (as mentioned in an interview).

When Scorsese joined, I felt it might be more fitting to have newer, energetic individuals who were just beginning their careers, fresh graduates from film school, people eager to prove themselves. I had the feeling that I was perhaps too experienced for the role.

It might seem unusual to some, but Brad Pitt is actually 11 years senior to Leonardo DiCaprio. In the movie “Meet Joe Black,” the role that Pitt initially had was eventually given to Matt Damon. However, Pitt continued to be involved in the project as a producer. The film “The Departed” won four Oscars, including Best Picture, Best Director, Best Adapted Screenplay, and Best Editing.

The story unfolds in South Boston, a city where law enforcement is waging war against criminal organizations. A fresh police officer named Billy Costigan, played by Leonardo DiCaprio, is assigned to go undercover and dismantle the crime syndicate led by Frank Costello (Jack Nicholson). However, matters become complex due to the presence of Colin Sullivan (Matt Damon), who maintains a secret identity as well.

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2024-08-16 17:03