Martin Scorsese’s status as one of the greatest filmmakers of all time is undeniable. From his humble post-film school beginnings working with the likes of Roger Corman to becoming one of Hollywood’s most revered elder statesmen, Scorsese’s career in the business has been an undeniable success. But for a long time, many people felt that he was still undervalued as a filmmaker, mainly for one major reason; because he hadn’t won an Oscar. After you’ve made movies as iconic as Taxi Driver (1976), Raging Bull (1980) and Goodfellas (1990), you would think that the Academy would’ve shown their love to Marty for all that he had done over his career. But, Scorsese continued to remain a consummate bridesmaid on Oscar night. This especially began to become an issue for many fans of the director during the 2000’s. Scorsese was reaching his 60’s and many worried that he would be overlooked while still in his prime, believing that as he reached his senior years that he would become as less productive and likely never get the chance to make that movie that would finally win him Oscar glory. But it wasn’t for lack of trying though. Martin Scorsese did manage to get a project he had long had in development finally across the finish line with his historical epic Gangs of New York (2002), starring heavy hitters like Daniel Day-Lewis and also marked his first collaboration with Leonardo DiCaprio. This would surely be the movie that would finally win him an Oscar, because it had all the ingredients that Oscar voters valued. But, despite quite a few nominations, Gangs of New York came up empty on Oscar night, with the Academy instead going for the musical Chicago (2002) that year, and Scorsese losing out Best Director to Roman “Statutory” Polanski for The Pianist (2002). For a lot of people this started to make them worry that Scorsese may never get his due honors, because if he couldn’t win it with a passion project he had been working on for decades then it may never happen. This only seemed to be reinforced when two years later he also struck out with the epic biopic The Aviator (2004). What would it take for Martin Scorsese to finally win the gold in the end. The answer would indeed be a bit surprising, and yet at the same time the most logical conclusion as well.
In the early 2000’s, Warner Brothers secured the rights to remake a Hong Kong action crime thriller called Infernal Affairs (2002). The original film, starring Andy Lau and Tony Leung, was about two men who become moles on opposite sides of the law. One is a police officer who has infiltrated a dangerous gang while the other is working within the police force to protect members of the Triad. Both have to maintain their cover and more importantly make sure that neither is aware of the other’s existence. Hollywood saw a lot of potential in this story, and were eager to bring it stateside as a action movie vehicle for some A-List stars. The decision was to bring the story to Boston, given it’s culture of the Irish American community falling into both sides of the law; often sometimes within the same families. One other reason for picking Boston as the setting was that the crime boss at the center would be largely based on real life Bostonian mafia leader James “Whitey” Bulger. To work on the adaptation of Infernal Affairs into this Boston set crime story, Warner Brothers tapped journalist turned novelist William Monahan to write the screenplay. Though Monahan was at the time a prolific writer, he was still fairly new to the art of screenwriting. He first got the attention of Hollywood with his original script Tripoli, a historical epic that got optioned in a six figure deal with Scott Free Productions, with the potential of being directed by Ridley Scott himself. Alas, Tripoli died quietly in development, but Ridley Scott wanted to keep Monahan around so the two of them worked together to create another epic movie set during the Crusades in the Holy Land. This became the film Kingdom of Heaven (2005), which was unfortunately heavily cut down by the studio and released in theaters to disappointing box office. Only in the years since has Kingdom of Heaven been reassessed by audiences thanks to a vastly superior 3 hour director’s cut released years later. But, even despite the disappointment in Kingdom of Heaven’s box office, people saw a lot of potential in Monahan’s work, and that’s why he seemed like an ideal choice for this project. For one thing, it would allow him to write closer to his own home given that he was a Boston boy himself. But what was especially important about Monahan’s writing is that it caught the interest of Scorsese, who decided on this new movie, now called The Departed, as his next project.
A crime thriller set in the mafia world is nothing new to someone like Scorsese. If anything, it’s a homecoming for him. With movies like Goodfellas and Casino (1995), Martin cemented himself as the quintessential mafia movie king; even eclipsing Francis Ford Coppola in this category. But a lot of those movies also tapped into his roots as an Italian American and as a New Yorker. Boston was an entirely different kind of city with an entirely different kind of mafia. The question would be whether or not Scorsese’s style would translate over into this new setting. Marty certainly seemed to think so, and him being attached to this project suddenly gave it a lot more prestige than it otherwise would’ve likely had before. With Scorsese now on board, the project was suddenly now glimpsed as an A-list production. But who would bring their star power to the roles in the movie. In particular, they needed to find the right actors to play the roles of the two moles, who in this film would be named William Costigan and Colin Sullivan. For the longest time, Brad Pitt had eyed the role of Sullivan, the mole on the inside of the Boston PD, and at one time he was hoping to rope in his friend and fellow A-lister Tom Cruise to play the role of Costigan in the movie. But, Cruise was less interested and passed on the part, and eventually Brad Pitt began to drift away from the project as well. Pitt did stay involved as a producer however under his Plan B production company, though most of the producing credit would go to Graham King, whom Martin Scorsese brought over with him from The Aviator. This producing credit would later lead to a bit of controversy later on. The casting of Frank Costello, the Whitey Bulger stand-in, would also be an important choice as well. Initially, Martin wanted to give the role to his long time collaborator Robert DeNiro, but DeNiro was too busy at the time working on his own directorial debut The Good Shepard (2006). Scorsese also offered the role to Al Pacino, who he had yet to work with at the time, but unfortunately the two would wait another 13 years before finally making a movie together with The Irishman (2019). While many of these actors would’ve certainly been interesting choices for this film, the movie would eventually benefit from the right actors getting the roles.
For one thing, Scorsese benefitted from there being Boston raised actors that were just right for the roles. One, of course, was Matt Damon, who was cast as Colin Sullivan. Damon of course made his mark alongside his longtime friend and fellow Bostonian Ben Affleck with their Oscar-winning Good Will Hunting (1997), which was a film steeped in the local flavor of the city. He also perfectly played into the good old boy facade that was needed for the role, given that he had to play a cop who was secretly helping the mafia from within. But, his role also had to have the perfect counterbalance on the opposite end. With the casting of William Costigan, Scorsese once again went with the leading man of his last two films, Leonardo DiCaprio, to play the part. DiCaprio of course neither has Irish ancestry nor is from anywhere close to Boston. And yet the chameleon like actor managed to find his way into the role and perfectly channel a Bostonian identity into the character. But, who would fill out the role of Frank Costello, the crime boss who looms large over everyone in the movie. Turns out there was another legendary actor that had never worked with Scorsese before who would be absolutely perfect for the part. Jack Nicholson had wanted to work with Marty for a long time, but things hadn’t aligned for both of them until now. At this point, Jack was eager to sink his teeth into a juicy villainous role, and the part of Frank Costello, with all of his menacing swagger and twisted sense of humor seemed to be tailor made for the actor. While DeNiro and Pacino would’ve certainly been solid choices too, it’s fortuitous that Nicholson ended up playing the part instead, because it allowed to Scorsese to differentiate this mafia movie from the ones he had made in the past. Nicholson’s Frank Costello was very much a product of the city of Boston and defined it’s very brash and very Irish identity. In addition to these actors, Scorsese round out his cast with some pretty heavy hitters, such as Alec Baldwin, Martin Sheen, Vera Farmiga, Ray Winstone, and Mark Wahlberg, who really tapped into his Bostonian roots with his scene stealing performance as Sergeant Dignam.
It’s undeniable that the city of Boston is a character in of itself within the movie. New York may run through Scorsese’s blood, but he did justice to the identity of Boston; capturing the swagger of the community beautifully in all of it’s hard edges. But even despite the change in scenery, the movie does feel in line with Scorsese’s Italian mafia epics of the past. This is thanks to him working with some of his trusted longtime collaborators. The Departed would sadly be the last time that Marty worked with his longtime cinematographer Michael Ballhaus, who had been working with Marty since 1985’s After Hours. Ballhaus only shot one more movie after The Departed and passed away in 2017 at the age of 80, capping off a storied career of shooting some truly beautiful films such as The Last Temptation of Christ (1988), Goodfella, and Bram Stoker’s Dracula (1992). Scorsese’s longtime friend and collaborator Thelma Schoonmaker also returned to edit this movie, fresh off an Oscar win for The Aviator. While their work on the film is not the flashiest they had ever done working with Scorsese, given the other movies listed, they nevertheless delivered a solid, well crafted movie that serviced the story well. There are some hauntingly beautiful moments that do bring out the best of their talents. One is the breathtaking opening montage that serves as the prologue of the movie, set to the Rolling Stones’ “Gimmie Shelter.” It’s an outstanding tone setter that primes you perfectly for the movie you are about to see, with Ballhaus’ striking camera work and Schoonmaker’s lyrical editing doing a great job setting up the city of Boston and the characters within in an almost mythical way. And like many of Martin Scorsese’s movies, the needle drops in the movie are especially poignant. Apart from “Gimmie Shelter,” there is also a haunting cover of Pink Floyd’s “Comfortably Numb,” sung by Irish R&B signer Van Morrison used halfway through the movie during a romantic moment. But no song got more of a boost from appearing in this film more than Celtic punk band Dropkick Murphy’s “I’m Shipping Up to Boston” which has almost become an unofficial anthem for the city, played at sporting events for the Patriots and the Celtics to this day.
But, how was the world going to receive this new Scorsese film. Despite the shift from New York to Boston, many thought this was just Scorsese falling back on old tricks by making yet another mafia movie. But, audiences responded quite well to the film. To this day, it is still Martin Scorsese’s highest grossing film at the box office, making $292 million worldwide, which is pretty good for an R-rated mafia movie. But, the question remained, would the Academy finally take notice. The film did receive nominations for Best Picture and Director, but it’s victory was not a guarantee as it only had 5 nominations total in a very competitive year. Not only that, but it would be a rematch of 2004, where Scorsese’s The Aviator lost out to Clint Eastwood’s Million Dollar Baby (2004). Eastwood, who’s clout with the Academy was undeniably strong, was nominated again for his WWII epic Letters from Iwo Jima (2006), and it was going to be a difficult choice between these two titans of the industry. But, it became clear through the night that this may have finally been the movie to get Marty up to the podium. Both William Monahan and Thelma Schoonmaker walked away with Oscar wins for their work on the film, giving the movie momentum. And then came the award for Best Director. Though the Academy didn’t know for certain given the secrecy of Pricewaterhouse Cooper’s ballot counting, they seemed to have a pretty good inkling about who was going to win given who they chose to present the Award. Walking onstage to present Best Picture were directing legends Steven Spielberg, Francis Ford Coppola and George Lucas. These weren’t just some of the biggest names in Hollywood, they were also longtime friends of Marty’s going all the way back to their early days in the 1970’s when they were just starting out in the business. It was an indicator that the Academy knew the time had come and they wanted to make the moment special. And sure enough, a great sigh of relief could be felt as Steven Spielberg read out the name of Martin Scorsese. He was a bridesmaid no more, and would now forever have the title of Oscar winner on his resume. And though deeply grateful, Scorsese also tried to keep it humble as well, joking to his friends, “can you check the envelope again, please?” But it was undeniable to everyone; this was a long time coming and very well deserved.
But, despite the fears that this would be Scorsese’s last chance to win the coveted Award, finally winning it didn’t cause Scorsese to slow down either. If anything, it rejuvenated his career. Scorsese has honestly put out some of his best work since The Departed, with movies like Hugo (2011), The Wolf of Wall Street (2013), The Irishman (2019), and Killers of the Flower Moon (2023), all of which he has received more Oscar nominations for. And this year, at the age of 83, he still has more movies in development with no indication yet that he’s ready to retire. Given his whole body of work, it’s actually quite unusual to think that The Departed was the one that got him on the Oscar stage. It’s not a particularly showy movie, with the movie most grounded in realism throughout. It’s also a movie that despite being a mafia film also feels the least like any of the other characteristically Scorsese crime epics. You would think that for Scorsese to get the attention of the Academy, he would’ve had to have made a film that showcased a lot more of his unique style, rather than just do a better than average competent action flick. But, that’s underselling what Marty achieved with The Departed. It is a brilliantly crafted character study about these two individuals who have to carefully maintain these facades within places they do not belong or else their lives will literally be destroyed. It’s ultimately a parable about paranoia and mistrust, and thinking that there is a rat in every corner of society. It’s no surprise that this movie existed in a post-9/11 world, where paranoia and distrust was rampant in American society. With the Scorsese touch, he made this cops and robbers thriller feel more reflexive and introspective of where America was standing at the time. In his hands, this story takes on a far greater mythical sense, showing how we as a society was starting to evolve, with the lines between good and bad, lawful and unlawful being increasingly blurred. A lot of people have critiqued the film over the years with regards to the final shot. In the closing moments, Scorsese holds on a window shot overlooking the Massachusetts State House, and in the foreground appears a literal rat. People thought this was too much of a heavy handed metaphor, but honestly after the chaos of what preceded it in the shocking third act of the movie, heavy handed symbolism does seem right in the parting shot of the movie.
20 years later and The Departed still holds up as one of the best mafia movies ever made. It may not be up to the epic level of The Godfather (1971), but it’s undoubtedly one of the best executed ones in the last quarter century and that’s thanks to the talents of Martin Scorsese. He took what could have been just another standard action thriller which are a dime a dozen in Hollywood, and created an Oscar winning movie out of it. Certainly a lot of that has to do with it’s absolutely perfect cast, with DiCaprio, Damon and Nicholson all delivering some of the best performances of their careers. It may be a subdued, by the numbers film for Martin Scorsese, but even with those limitations he still managed to deliver an all time classic under his direction. And as we’ve seen, he still is not done yet. William Monahan, who also came away an Oscar winner, has continued to work as a screenwriter on several more movies, and has even directed a couple as well. Leonardo DiCaprio has also continued to remain a favorite of Marty’s, and they have worked on many more films together since, including The Wolf of Wall Street and Killers of the Flower Moon. Matt Damon has also continued to remain an A-lister in Hollywood, and though he has not worked with Scorsese again since The Departed, he still considers his work in the movie to be some of the best he’s ever done. This also has marked one of the last great roles for Jack Nicholson. Though as of this writing Jack Nicholson is still alive and well at the age of 89, but he has not made a new film in 16 years, retiring after a small part in James L. Brooks’ How Do You Know (2010). The Departed is looked at as the last true Nicholson star role, and it’s great that he and Marty’s paths managed to cross and result in this film before he called it quits. One of the benefits of making The Departed the way he did is that it gives Scorsese a film with a bit of universal and timeless appeal. You don’t have to be familiar with what Scorsese has done prior to enjoy the movie. It stands apart from his other work in a good way. That’s why it’s Oscar win for Best Picture hasn’t aged one bit since it happened, because the movie still works just as well today as it did 20 years ago. Sure, Scorsese deserved the Oscar much more for many other movies prior, but I don’t hear too many complaints about this being the one that got him there. Often a filmmaker will end up winning the top award for a movie that wasn’t quite representative of the filmmaker they really are. Here, I think it works better for Scorsese that he won for this movie rather than a traditional Oscar bait flick like Gangs of New York or The Aviator. The movie may have been outside of his comfort zone of the streets of New York, but it’s fitting that by going to Boston that Scorsese still won the award for a mafia movie; the kind of film that he did better than anyone else.
