Martin Scorsese is considered to be one of the greatest directors in cinema history, so it makes sense that he has been nominated for the Best Director Oscar nine times over the years. What’s shocking is that he has only won the award once. It wasn’t for Taxi Driver, he wasn’t even nominated for that one. It wasn’t for Raging Bull or Goodfellas. It was for The Departed, a crime film set in Boston but based on a Chinese production. Featuring an incredible all-star cast, The Departed was named the Best Picture of 2006 and allowed Scorsese to take home the gold for Best Director.
Before there was The Departed, there was Infernal Affairs, a 2002 movie that took place in Hong Kong, directed by Andrew Lau and Alan Mak from a screenplay Mak wrote with Felix Chong. The basic concept was inspired by John Woo’s Face/Off, which shows a cop and a criminal swapping identities. And faces. Inspired to do a more realistic version of that scenario, the makers of Infernal Affairs crafted a story about a corrupt cop who reports to a gangster. The story also focuses on one of the gangster’s lackeys, who is actually an undercover cop. The movie was an award winner at home and abroad, a critical success around the globe, and such a financial success that it spawned a prequel, a sequel, and a TV series. And, of course, it caught the attention of Hollywood.
Warner Bros. and Brad Pitt’s production company Plan B secured the rights to make an English-language version of Infernal Affairs. The idea was that Pitt would star in the remake, in addition to producing it. It wasn’t clear if Pitt would play the crooked cop or the undercover cop, but there was some hope that after he chose one the other role would go to Tom Cruise. Warner Bros. and Plan B then picked William Monahan to write the screenplay. Monahan had written an adaptation of his novel Light House, sold a spec script about the Barbary Wars called Tripoli, and wrote an early draft of Jurassic Park 4. None of those got made, but around the time he was hired for the film that would become The Departed he was also working with Ridley Scott on Kingdom of Heaven, his first produced screenplay. When given the job to transplant a Hong Kong crime story to America, many writers probably would have set the action in New York. But Monahan was from Boston, and chose to set his version of the story in his hometown, which had plenty of crime of its own. Monahan was specifically able to draw inspiration from the story of Boston crime boss and FBI informant Whitey Bulger.
Monahan chose not to watch Infernal Affairs because he didn’t want the film to influence his writing too much. But he did read the translated script, and stuck very closely to it for his English adaptation. The Departed follows the story of Infernal Affairs and keeps all of the major scenes and sequences intact. It also spends more time setting up situations and digging into characters. Some of the things Monahan added to the story seem like they were inspired by elements of Infernal Affairs 2 and 3, but he said he never read those until well after The Departed had been released.
Once the script was complete, it made its way into the hands of director Martin Scorsese, the go-to guy if a studio wants to make a prestigious crime movie. The script was also sent to actor Leonardo DiCaprio, who Scorsese had recently made Gangs of New York and The Aviator with. Scorsese and DiCaprio read the script the same day, and called each other the next day to confirm that they were both in. Scorsese hadn’t seen Infernal Affairs yet, which is somewhat surprising, given what a cinephile he is, but he was drawn to the material because the set-up of an undercover cop dealing with a mobster reminded him of the 1949 classic White Heat.
DiCaprio wasn’t sure which role he wanted to play, so Scorsese decided he should be Billy Costigan, the undercover cop. This was the character DiCaprio was more nervous to play, because Billy is constantly in fear for his life as he deals with the mobsters. His cover could be blown at any moment. They could find out he’s a cop and kill him. DiCaprio described the character as experiencing a “constant, twenty-four hour panic attack.” Now Scorsese had to fill out the cast around DiCaprio – which proved to be more difficult than you might imagine. Since DiCaprio was on board, Pitt decided to step away because he thought Billy’s counterpart should be played by someone younger. After all, Pitt and DiCaprio are about eleven years apart in age. So the role of crooked cop Colin Sullivan went to Matt Damon, who is just four years older than DiCaprio. Scorsese felt Damon had a cocky attitude and bravado that would be perfect for Colin.
Scorsese had Al Pacino in mind for mob boss Frank Costello, but Pacino wasn’t interested, so the role was offered to Jack Nicholson. Nicholson read the script and also turned it down. He wanted to play a villain after working on a string of comedies, but he felt that the Costello character was underwritten. So Scorsese did the logical thing: he promised Nicholson the character would be expanded. Much of what we see from Costello in the finished film was brought to the table by Nicholson, who wanted to play the guy as the ultimate incarnation of evil. Monahan had written Costello as a post-sexual old man; Nicholson turned him into a lascivious slimeball. He made his character so sexual, Damon suggested going the opposite way with his. They added moments where it’s implied that Colin is impotent. Since the cast was going to be packed with tough guy characters, Damon also wanted to make sure his character would lose every fight he gets in.
Nicholson improvised many of his scenes, which was fine by Monahan, who said the actor may have changed some of the words that were written for him, but he didn’t change the good ones. DiCaprio knew going into any scene with Nicholson that he should expect the unexpected, which helped him play his own perpetually nervous character, because he never knew what Nicholson was going to do. He really was on edge.
Only two people on the police force know the identity of the undercover cop they have embedded in Costello’s organization. They are Captain Queenan and Staff Sergeant Dignam. Scorsese envisioned these roles as being a Goodfellas reunion: he wanted to cast Robert De Niro and Ray Liotta. But De Niro was gearing up to direct The Good Shepherd and Liotta had scheduling issues, so they both had to decline. Gerard McSorley was cast as Queenan and had even met with Boston police officers to research the part before he was notified that Scorsese was going in a different direction. That direction was casting Martin Sheen in the role. Denis Leary was offered the role of Dignam, but couldn’t do it. So Scorsese offered the role to Mark Wahlberg, who didn’t want it. Like Nicholson with Costello, Wahlberg didn’t like how the Dignam character was written in the script. Scorsese had to talk him into accepting the role by assuring him that he’d be able to rework the character. Scorsese asked Mel Gibson to play police Captain Ellerby, but he was another actor who had to turn down an offer to be in The Departed, because he was busy working on Apocalypto. So the role went to DiCaprio’s The Aviator co-star Alec Baldwin.
In the original Chinese film, the crooked cop character is engaged to a woman named Mary. The undercover cop has regular appointments with a therapist named Lee Sum-yee, who he has fallen for even though she’s taken. Monahan combined those two characters into one, which was a clever choice. Billy falls for his therapist, Doctor Madolyn Madden, who also happens to be in a serious relationship with Colin. Scorsese considered several actresses for Madolyn: Emily Blunt, Hilary Swank, Kate Winslet, even producer Brad Pitt’s then-wife Jennifer Aniston. He ended up casting the up-and-coming Vera Farmiga because he had been impressed by her work in the 2004 movie Down to the Bone. While trying to figure out how to approach the character, Farmiga showed the script to a real police psychiatrist – who thought the writing of Madolyn was preposterous. There was no way a police psychiatrist would interact with a patient the way she does with Billy. She wouldn’t behave that way, and she definitely wouldn’t sleep with him. When she realized how far outside the norm Madolyn is, Farmiga became even more interested in diving in and bringing her unusual behavior to the screen.
Farmiga isn’t the only one who met with a real world counterpart to her character. DiCaprio went to Boston and met with people who were allegedly connected to the Irish Mob. The actors playing police officers met with real Boston cops and worked closely with technical advisor Thomas Duffy, who had just retired as a Major in the Massachusetts State Police. Damon even got to ride along on a police raid of a crackhouse – although they took twice as many officers on the raid than they would usually take, and they kept Damon, who was wearing a bulletproof vest, behind all of them. They didn’t let him enter the crackhouse until they made sure the place had been cleared. But still, he got to see how a crackhouse raid works in person.
With the leads cast, Ray Winstone was chosen to play Costello’s right hand man Frenchy. And even though Costello and Frenchy are close, Winstone felt like Nicholson didn’t like him. Anthony Anderson and James Badge Dale were cast as troopers Billy and Colin first meet during their training. There’s also David O’Hara and Mark Rolston as a couple of Costello’s lackeys, Kevin Corrigan as Billy’s troubled cousin Sean, and Kristen Dalton as Costello’s much younger girlfriend Gwen.
Scorsese has said that “Infernal Affairs is a very good example of why I love the Hong Kong cinema, but The Departed is not a remake of that film.” He feels that Monahan did such a good job of immersing the story in its new Boston setting, it no longer qualifies as a remake. But the fact is that Andrew Lau, Alan Mak, and Felix Chong provided the blueprint for Scorsese and Monahan to follow – and we got two great movies out of it, each with their own distinct personality and setting. The Chinese movie already proved that the set-up, structure, and sequences worked. And of course, Scorsese had no problem bringing these things to the screen effectively in his own way. Where the two movies most strongly stand apart are in the performances of the actors and the portrayal of the characters.
It may have been a struggle to fill the roles in The Departed at times, but Scorsese ended up with the right cast for the film. Every actor in the movie perfectly inhabits their character and makes their actions believable, even when their actions are preposterous, according to the psychiatrist Farmiga talked to. Other than the White Heat similarities, Scorsese was also drawn to Monahan’s script because of the way it dealt with trust and betrayal, and the movie is a fascinating examination of those topics. The lead characters are all betraying trust in some way. Colin is betraying the police force to protect Costello, a man he has known since he was a child. Billy is betraying Costello, working for the police. Madolyn betrays Colin by sleeping with Billy. And characters are also betraying their own personalities. Colin is a criminal masquerading as a cop. Billy is a good cop who has to play at being a criminal.
The stress and fear Billy feels in most of his scenes is palpable, and it makes sense because he has to endure some awful situations with Costello. DiCaprio said Nicholson could “go off the cuff and just say anything or do anything. In character, it instills this constant fear in you.” Completely unleashed, Nicholson could be accused of going over-the-top at times, but he still succeeds at what he wanted to do. He wanted to play Costello as a monster. That’s how he comes off in the movie. Especially in moments like the scene where he nonchalantly handles someone’s severed hand while having a conversation with Billy. He is despicable, and his violent, unpredictable nature makes us concerned for Billy’s safety. While Billy is falling apart out in the field, Colin is living the good life. He has a nice apartment, a comfortable job in the Special Investigations Unit, and he proves to be quite monstrous himself at times. He will destroy the lives of innocent people, get them killed, and laugh about it. We want to see Colin get his comeuppance, but he always seems to come out of things unscathed. Usually with a promotion. We can only hope his luck is going to run out at some point.
Most of the characters in The Departed aren’t quite as lucky as Colin. A lot of people die over the course of this movie. And if you want to know ahead of time who’s not going to make it, there is a game you can play while watching the movie. Watch for the X. Scorsese had fun putting in subtle foreshadowing of deaths by putting an X in the frame at some point with characters that are going to die. It’s an idea he lifted from director Howard Hawks’ 1932 version of Scarface.
The Departed is so vile, violent, and dark, it actually got to its own director. Scorsese has said that the post-production process on this one was highly unpleasant because he had to spend so much time focused on these characters and the subject material. He said, “I don't care how much I'm being paid, it'll kill me. I'll die. Very simply.” He took to calling the movie Moral Ground Zero and didn’t do much press for it when it was released. He was proud of the movie, but he was also tired of it. He found it maddening. He told associate producer Emma Tillinger that they wouldn’t have to worry about going through the awards season routines, as there was no way a movie like this was going to receive any nominations.
But, of course, it did receive many awards nominations, and won awards from several different organizations. Leonardo DiCaprio, Jack Nicholson, and Mark Wahlberg earned Golden Globe nominations for their performances. The movie was also up for best dramatic motion picture and best screenplay. But the sole Golden Globe it won went to Scorsese for Best Director. Shockingly, Wahlberg was the only actor to receive an Academy Award nomination for this movie. DiCaprio was in the running for Best Lead Actor that year, but not for The Departed. He was nominated for Blood Diamond. Warner Bros. had tried to get him a Supporting Actor nomination alongside Wahlberg, but it didn’t work out. The Academy was content to just acknowledge his work in Blood Diamond.
While the Academy largely overlooked the cast, they made sure to show their appreciation for the film in other categories. While Scorsese figured the biggest awards were going to go to the movie Babel, it turned out to be The Departed’s night. Monahan won the Best Adapted Screenplay Oscar, Thelma Schoonmaker won for the editing, and for the first and, to date, only time, a Scorsese movie won Best Picture. Plus, Scorsese finally won his Best Director Oscar. It was his sixth time being nominated. Fittingly, the Oscar was presented to him by his old friends Steven Spielberg, Francis Ford Coppola, and George Lucas.
As for what the makers of Infernal Affairs thought of The Departed... well, they preferred their version of the story. Actor Andy Lau, who played the crooked cop character in the Chinese film, thought The Departed was too long. And at a hundred and fifty-one minutes, it is fifty minutes longer than Infernal Affairs. The film’s director Andrew Lau, not to be confused with Andy Lau, gave The Departed an eight out of ten score and said, “Of course I think the version I made is better, but the Hollywood version is pretty good too. Scorsese made the Hollywood version more attuned to American culture.” He thought the remake had some great dialogue in it, but also too much profanity. It has been said that there are over two hundred and thirty F-bombs in The Departed – and Monahan claims he didn’t script that many. It’s just that, as he said, actors come to the set of a Scorsese movie prepared to swear their heads off. Clearly the Academy can’t be put off by swearing.
The Departed wasn’t just a success with critics and awards organizations, it was also a financial hit. Made on a budget of ninety million dollars, it earned close to three hundred million at the global box office. That makes it one of the biggest hits of Scorsese’s career, surpassed only by Shutter Island and The Wolf of Wall Street, movies that also starred Leonardo DiCaprio.
It’s no surprise that there was talk of a sequel being made, especially since Infernal Affairs became a franchise. Monahan had the complete story for a follow-up in mind – one that would have left the Infernal Affairs connections behind to show what was going on with Dignam before, during, and after the events of The Departed. He and Wahlberg pitched it to Warner Bros. together, and were hoping to get Brad Pitt and Robert De Niro into the cast of this one. But it never got off the ground. And Scorsese had no interest in returning to the world of The Departed anyway. One trip to Moral Ground Zero had been enough for him.
So all this time later, The Departed remains a standalone movie, and it works perfectly as one. It’s highly respected, and a bright spot in the careers of Scorsese and the actors involved. There is just one dangling, unanswered question... what is in that envelope Billy gave to Madolyn near the end of the movie? It looks like we’re never going to know.
Note: Much of this article was originally written as a script I put together for a video on JoBlo YouTube Network.
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