I think most people who love cinema can pinpoint a specific film that inspired their love for it. For me, that movie is The Departed.
Before I’d seen Martin Scorsese’s 2006 epic crime thriller, I watched movies like pretty much all young people do: you basically just sit down, you watch it, and you go about your day. After seeing The Departed for first time when I was about 12 or 13 years old, I started thinking about films in a different way. I began paying attention to who was involved in making the movie, what the filmmaker and the film had to say, and how it made me feel.
The Departed was the first “adult” movie I recall having discovered on my own. Well, not really on my own: my brother and a friend saw it first, and after we eventually got our hands on the DVD, it stayed in steady rotation for years. Full disclosure, in retrospect, we probably saw it a few years earlier than we should have, but it’s the first movie of its kind – a movie made by adults, for adults – that felt like it was mine.
The Departed, which is based on the 2002 Hong Kong crime drama Infernal Affairs, begins in Boston in the 1980s. Irish mob boss Francis “Frank” Costello (Jack Nicholson) meets a local youngster named Colin Sullivan. Frank takes Colin under his wing, and years later, the now-grown Colin (Matt Damon) joins the Massachusetts State Police with one goal: to serve as a spy for Frank.
Police academy trainee William “Billy” Costigan Jr. (Leonardo DiCaprio), meanwhile, meets with Captain Oliver Queenan (Martin Sheen) and Staff Sergeant Sean Dignam (Mark Wahlberg on an absolute heater in every scene), who recruit him to infiltrate Costello’s operation to help take him down. Despite wanting to be a cop, Billy has family ties to the Boston underworld – something Queenan and Dignam seek to exploit. Seeing as his late uncle Jackie Costigan wasn’t exactly a model citizen, it would reasonably make sense that Billy got kicked out of the police academy and decided to play for the other team – specifically, Frank’s. Billy does some time in jail for assault and battery (a ploy concocted by Queenan and Dignam to boost his street cred) and before long, he’s a grunt on Costello’s crew.
Over time, Billy gains the trust of Frank and his merry band of criminals, but at a cost. Billy begins to succumb to the pressure that comes with living such a dangerous double life – after all, if Frank were to ever find out that he’s a cop…well, it’d be fade to black on our guy Bill. Billy grows increasingly reliant on prescription medications to calm his nerves, and his physical appearance deteriorates alongside his mental health. As part of his release from jail, Billy’s required to see a therapist, who just so happens to be Colin’s fiancée, Madolyn (Vera Farmiga).
While Billy’s Not Having A Great Time, Colin’s quickly rising through the ranks of the State Police. But, there’s trouble brewing in Beantown! Queenan tells Colin that he suspects Costello’s got a mole in the Special Investigations Unit, and he tasks Colin with finding out who it is. The problem? It’s Colin!
At the same time, Frank informs Billy that he thinks he’s got a rat in his crew (a correct assessment!), but Billy’s able to convince Frank it isn’t him (it is!).
Billy works to make sure Frank and the gang trust him while Queenan and Dignam use Billy’s evidence to build a case against Frank, and Colin tries to conduct an investigation he knows can’t actually end with putting the mole behind bars, because, well, he is said mole. Billy’s terrified that Frank is eventually going to find out who he really is, and Colin begins to suspect that Frank could give him up in an act of self-preservation.
And therein lies the drama at the center of The Departed. Billy and Colin each know there’s an informant on the inside of their respective organizations, but they don’t know who they are specifically. The film more or less becomes a race between Billy and Colin to identify the other, all while keeping up appearances to make sure Frank and the cops remain none the wiser to their true intentions.
Scorsese, the master that he is, does a bang-up job of building up the tension, and as the story careens towards its explosive conclusion, the whole thing reeks of stress and paranoia (complimentary). The web of deceit and anxious suspicion entangles everyone to some extent; almost no one walks away untouched. Billy inches closer and closer to a full-on mental breakdown; Colin’s relationship with Madolyn starts to go down the tubes as he fears betrayal by Frank; and Frank descends into dark, violent, volatile mania. The development of a relationship between Billy and Madolyn adds another effective dramatic wrinkle.
One of the chief reasons this movie has had such a profound impact on me is its unforgettable characters.
Let’s start with Frank’s henchmen. This is simply a top-tier assortment of scumbags. The menacing stoicism of Frank’s right-hand man, Mr. French (Ray Winstone), is the perfect complement to Frank’s charisma and unpredictability, and the crew is rounded out by several of the city’s best, albeit not brightest, goons. It’s the A-Team of Boston Bad Guys.
Then we have the legend Jack Nicholson doing some of the most perplexing yet exhilarating work of his career. In a column from 2023 about The Shining, I wrote about Nicholson holding the Going Insane Championship Belt, and he defends his title in The Departed. At times I’m not sure he knows exactly what movie he’s in, and his vaguely Boston-adjacent accent kind of comes and goes, but Nicholson nevertheless gave us his one-of-a-kind vision of a psycho in a tailspin. It’s a completely singular performance.
As Billy, DiCaprio delivers one of the more underrated turns of his celebrated career. Leo perfectly captures the essence of a man on the verge of all-out collapse – sweat, tics, and wide, darting eyes with dark bags beneath them. But, in impressively deft and reliable Leo fashion, he gives Billy emotional depth – something that in itself has kind of become somewhat underappreciated in his performances due to his unwavering consistency. Billy’s a good guy pretending to be bad, and you can’t help but hope he sees the other side of his ordeal.
Damon does excellent work playing a man who is essentially Billy’s inverse. Colin’s got a comfortable life, a rising career, and a solid relationship. It’s the kind of stability that Billy lacks, and desperately needs. But whereas Billy, to a certain extent, at least can see the light at the end of the tunnel as far as his professional charade goes, Colin’s entire life is a lie. He’s just bright enough to pull it off, but just arrogant and naive enough to not realize there aren’t many positive outcomes for him.
What’s so great about The Departed is that although the focus is largely on the characters played by DiCaprio, Damon, and Nicholson, the supporting cast is one of the best ever assembled. Although Sheen’s Boston accent could’ve used a little polishing, he’s tremendous as a rare beacon of steadiness in Billy’s life. Alec Baldwin’s in just a few scenes as Police Captain George Ellerby, and the man cranks it to 11 every time, dropping some of the movie’s funniest lines.
But hands down, Wahlberg steals the show. Wahlberg, like Damon, is a Boston native, and he imbues Dignam with his takes on various cops he’d encountered during his somewhat tumultuous youth. He’s brash, he’s rude, he’s offensive, he has a questionable haircut, and he’s just an absolute powerhouse. It’s my favorite Wahlberg performance, and in hindsight, it’s pretty cool that he won an Oscar for it.
In more ways than one, The Departed is classic Scorsese; I mean, it’s an exciting gangster movie peppered with Rolling Stones tunes. But make no mistake – Scorsese isn’t glamorizing lawlessness here. As he did so masterfully with Goodfellas, Scorsese with The Departed shows us that the extravagance of the criminal lifestyle is not worth the cost. The bill always comes due, sooner or later. And my goodness, is that ever the case with the characters at the center of The Departed.
The Departed might be the most influential movie in my life. It changed how I consume and understand pop culture, and it directly led to me sitting on my couch, writing this column.
If you’re in the mood for a violent, vulgar, hilarious, live wire of a film, fire up The Departed – and maybe treat yourself to a cold beverage while you’re at it. Might I recommend a cranberry juice?
Jalen’s columns, “Movies You Gotta See” and “The Free Play,” can be found online at www.medium.com/@jalenmaki.
Follow Jalen on Letterboxd at www.letterboxd.com/jalenmaki182/ to see what he’s been watching.
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