It was only fitting that Martin Scorsese got his long overdue Oscar for The Departed, a gangster film, the genre that helped launch his career. The film, which saw Scorsese direct an all-star cast including Leonardo DiCaprio, Matt Damon, Jack Nicholson, Vera Farmiga and Mark Wahlberg, among others, is officially 15 years old, so what better time for behind-the-scenes facts about its making.

Grab your flip phone and imagine you’re reading the following in an in-and-out Boston accent like Jack Nicholson (sorry Jack).

By Michael Balderston

Despite the inconsistencies of Jack Nicholson’s Boston accent in the film, the actor delivered an incredible performance in his first (and thus far only) film with Martin Scorsese as the villainous mob boss Frank Costello. It’s widely reported that Costello was based on famed Boston gangster Whitey Bulger, however when Nicholson first read the screenplay he actually turned Scorsese down.

In a 2006 Variety piece profiling Nicholson as an Oscar hopeful for The Departed, the actor said that the character didn’t really exist in the way we see him in the finished film. It was DiCaprio and Scorsese that pushed for Nicholson to join the cast, and the actor says he agreed in large part to work with them.

They of course did build out the character of Frank Costello, “layer by layer” as Nicholson put it. He would go on to add his own flare to the role with things not in the script, but more on that in a bit.

Leonardo DiCaprio was one of the first people involved with The Departed. He had previously worked with on Gangs of New York and The Aviator. What DiCaprio apparently wasn’t sure of right away was which role he preferred between the film’s two central moles, Billy Costigan or Colin Sullivan.

DiCaprio, in a press junket interview for the film said that he was open to playing either Billy or Colin because he saw a great duality in them, describing them as two sides to the same coin that ended up on their divergent, but collision-bound, paths because of the choices that they made. Scorsese was the one who decided he would be best suited for Billy, though DiCaprio wasn’t as confident at first, saying he had to figure out how to play the role. 

"The hardest part was what do I convey to the audience if I’m surrounded by killers all the time and I have to pretend to be somebody that I’m not. I didn’t initially know how to play it. It really helped in scenes when Nicholson is holding a gun to your face and making you beg for your life, the character, you come up with dialogue, you come up with things to say to survive. That was one of the first scenes that I had and it really helped me in discovering the character, the panic attacks he had and the fear for his life on a constant basis."

With The Departed, Leonardo DiCaprio and Martin Scorsese were working on their third straight movie together (to date they have worked on five together, with potentially more on the way). These frequent collaborations led many to describe DiCaprio as Scorsese’s modern-day Robert De Niro, as the director and Oscar-winning actor had worked together memorably on films including Mean Streets, Taxi Driver, Raging Bull, Cape Fear and Goodfellas (and a little less memorably in New York, New York).

Well we almost got both of Scorsese’s muses in the same film, as De Niro was at one point considering taking a role in The Departed.

In a story by Vanity Fair, De Niro nearly signed on to The Departed for an unspecified role (some reports say it was for the Martin Sheen role of Captain Queenan), but he ultimately decided to direct his own film, 2006’s The Good Shepherd, which starred another The Departed actor, Matt Damon.

Scorsese and De Niro did later reunite for 2019’s The Irishman.

Had original reports worked out, the starring roles in The Departed could have been very different, including having Brad Pitt star.

One way that it could have looked was Pitt alongside Tom Cruise. We don’t know how far along things got with this possible combination, but certainly at one point Pitt seemed like he was going to be the pick for one of the two leads as a press release from 2004 announces him as starring alongside DiCaprio in the Scorsese picture, when it was still simply referred to as a remake of the Hong Kong gangster film Infernal Affairs.

Ultimately, Pitt turned the role down and in came Matt Damon. However, Pitt stayed involved in the film as a producer through his production banner Plan B Entertainment. He would also get the chance to star with DiCaprio years later in Once Upon a Time... in Hollywood.

Vera Farmiga is really the only female character of note in The Departed, playing Madolyn, a psychiatrist who marries Damon’s Colin while also forming a deep connection with DiCaprio’s Billy.

Similarly to DiCaprio, Farmiga wasn’t immediately sure how she was going to play Madolyn, though she recognized that the character appears to be controlled by her Id, which she saw as a fatal flaw. Interested to learn more, she actually decided to talk with a police psychologist of the LAPD.

In a press junket interview, Farmiga said: 

I said, ‘what do you think about her? Tell me who she is? … What are your thoughts?’ She [the psychologist] was like, ‘No. No. There is no way she would behave this way. Absolutely not, it’s preposterous.’ And I thought, ‘Aha.’ That’s when I found her incredibly interesting.

Farmiga is able to stand tall among her co-stars, so what she was able to glean from someone that would have been her character’s contemporary was incredibly useful. 

The significance of the Xs in The Departed is essentially common knowledge at this point. But in case you aren’t aware, the next time you are watching the film keep an eye out for any Xs appearing around key characters - it means that they are marked for death.

What you may not know is that this is actually in reference to another classic gangster film. Scorsese is a student of film history, and this tactic was previously used more than 70 years before The Departed came out in 1932’s Scarface directed by Howard Hawks. The use of an X to foreshadow death was an homage by Scorsese to Hawks.

Sometimes you just have to tap out on something you’re working on. Martin Scorsese can recognize this, as he recalled in an interview with the U.K.’s Sunday Times that the process of making The Departed was highly unpleasant, especially when it came to putting it together in post production.

Scorsese said:

Of course, Scorsese rallied from this and has continued making movies even as he approaches 80 years old, though not a Departed sequel.

By 2006, the idea of an “Oscar movie” generally conjured an idea of a period/biographical or heavy drama that made audiences feel with a capital F, despite winners in the most recent years preceding 2006 included Lord of the Rings: The Return of the King, musical Chicago and sword-and-sandal epic Gladiator amid Million Dollar Baby, Crash and A Beautiful Mind. Still, it was said that Martin Scorsese apparently did not think his latest gangster film would be the one to break his losing streak at the Oscars.

In a story from The Wrap, frequent Scorsese collaborator Emma Tillinger-Koskoff said while the director was extremely proud of the film, he thought it was too violent and vile to be accepted by the Academy. This probably helps explain Scorsese’s surprise when he is announced as the winner of Best Director for The Departed.

Of course, the Academy would follow up The Departed’s win with another dark tale in 2007’s No Country for Old Men. Just goes to show you, sometimes the Oscars can make some bold choices.