The Departed Turns 20: Brad Pitt Beat Harvey Weinstein’s Miramax to the Rights, Then Gave His Role to Matt Damon

Twenty years ago, Martin Scorsese’s The Departed opened in movie theaters on October 6, 2006. But before it became the classic it is known as today, the film had a very different beginning – with an entirely different cast as the leads. While most people know about  Al Pacino and Robert De Niro passing on parts, must people don’t know that Brad Pitt actually helped get the film made, then gave up his role as Colin Sullivan to Matt Damon. Jack Nicholson, on the other hand, actually wouldn’t sign to star until his role was completely rewritten.

Back in 2006, The Departed marked a turning point for Martin Scorsese. As part of the pivotal New Hollywood generation that also gave us acclaimed talents such as Francis Ford Coppola, Steven Spielberg, and Robert Altman, Scorsese’s illustrious career since his 1973 gritty breakthrough, Mean Streets, had earned him several accolades.

Martin Scorsese Won Best Director for The Departed on His Sixth Nomination

The Academy may have snubbed him out of the much-deserved Best Director slot for Taxi Driver, one of the most shocking omissions in Oscar history; he would go on to receive five nominations between the 1980s and 2000s.

On paper, that would be an impressive feat for any director. And yet, the ever-conservative Academy often favored safer or sentimental choices; Scorsese’s Raging Bull and Goodfellas lost to Robert Redford’s Ordinary People and Kevin Costner’s Dances with Wolves, respectively. Given his caliber, it’s hard to believe Scorsese went five straight losses up to The Aviator, where he lost to Clint Eastwood for Million Dollar Baby.

It wasn’t until his sixth Best Director nomination for The Departed that he finally earned the long-overdue Oscar, beating fellow heavyweights such as Clint Eastwood for Letters from Iwo Jima and Alejandro González Iñárritu for Babel. The movie also took home three more awards, including the coveted Best Picture. It even did great at the box office, earning over $290 million on a $90 million budget (it also holds a 91% Tomatometer score and a 94% Popcornmeter audience score on Rotten Tomatoes).

How Jack Nicholson’s Improvisation Shaped Frank Costello in The Departed

The Departed boasts an all-star cast just like Infernal Affairs. One of them is Jack Nicholson, who plays the mob boss Frank Costello, showcasing improvisational acting that blends formidable and eccentric qualities, easily one of the best antagonist roles of his career. Scenes like Costello pulling out a gun before pointing it at Leonardo DiCaprio’s Billy Costigan reportedly weren’t actually in the script, which caught the latter completely by surprise. That genuine look at DiCaprio’s startled expression led Scorsese to keep the scene in The Departed.

Then, there was another part where Costello was throwing cocaine all over the prostitutes. And interestingly, there was a scene where the filmmakers wanted Nicholson to put on a Boston Red Sox cap, which suited his character, Costello, who was Irish-American and supposedly inspired by the real-life Boston crime boss Whitey Bulger. But it turned out that Nicholson refused to wear it since he happened to be a die-hard New York Yankees fan.

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Al Pacino Was Reportedly Scorsese’s First Choice for Frank Costello

But it’s hard to believe Nicholson wasn’t the original choice to land the role, as Scorsese reportedly wanted Al Pacino in the first place. The idea of two Hollywood legends, Scorsese and Pacino, collaborating for the first time would make The Departed a can’t-miss cinematic experience.

Unfortunately, it didn’t work out as planned when Pacino reportedly turned it down, even though the latter eventually starred in The Irishman thirteen years later. Scorsese moved on to his next best alternative, but then again, Nicholson didn’t immediately say yes to the opportunity. Apparently, it has to do with the Frank Costello character originally written as a small role, where Nicholson needed a part that truly interested him rather than just an idea he liked.

Still, Scorsese didn’t give up, prompting William Monahan’s script to be rewritten to turn Frank Costello into a bigger, more substantial role. Scorsese even worked with Nicholson to elevate the role with a fresh perspective, aimed at making Costello an evil godfather rather than yet another black-suited mob boss who wields power quietly.

Why Robert De Niro Turned Down The Departed for The Good Shepherd

At one point, Scorsese and Robert De Niro, who had worked together eight times, from Mean Streets right up to Casino, were tipped to reunite for The Departed. The Oscar-winning actor, who won for his role as Jake LaMotta in Raging Bull, was originally offered to play the supporting role as Captain Oliver Queenan.

In a perfect world, De Niro wished he “could’ve been able to”, but his hands were tied at the time in pre-production for producing and directing The Good Shepherd, forcing him to decline the offer, despite his efforts to make it work.

The Queenan role eventually went to another veteran actor, Martin Sheen. Fortunately, Scorsese and De Niro’s long-awaited reunion finally happened when they collaborated on The Irishman and Killers of the Flower Moon.

Why Brad Pitt Gave Up His Role in The Departed

Back in 2003, Warner Bros. and Brad Pitt’s Plan B studios first won a bidding contest (against some of the biggest studios at the time, including Harvey Weinstein’s Miramax) for the Infernal Affairs remake rights. Pitt who was meant to play Colin Sullivan later said the leads should be younger. Pitt stayed on as a producer, while Matt Damon grabbed the role (one of his best of all time).

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So, who would you rather have seen as Frank Costello? Was Jack Nicholson perfect or could Al Pacino have been better? Let us know in the comments.

The Departed is available to stream on Hulu and for rent or purchase on Apple TV and Prime Video.