The story of James “Whitey” Bulger, the Southie mob boss who also acted as an FBI informant, is unquestionably an exciting tale of intrigue, violence and betrayal—and hopefully, someone will film it someday. Until then, we have something nearly as good: The Departed, a gripping, irreverent and strangely hilarious take on Beantown crime and punishment directed by Martin Scorsese and featuring Jack Nicholson.

From what I know of Bulger, he was charismatic and cunning—not unlike Frank Costello, the character that Nicholson portrays here. But the Bulgerisms in The Departed are deceptive: This film is actually based on a 2002 Hong Kong thriller called Infernal Affairs, which was retooled into a South Boston setting by screenwriter and Beantown native William Monahan.

The plot is relatively simple: Costello plants fellow gang member Colin Sullivan (Matt Damon) in the police department as a spy in order to stay one step ahead of the law. Meanwhile, the cops plant their own agent—Billy Costigan, played by a disarmingly intense Leonardo DiCaprio—in the gangster’s organization. There’s also the wholesome-but-sexy love interest, psychiatrist Madolyn (Vera Farmiga), who becomes involved with both men. As the two spies get closer to discovering each other’s identities—and both the gangsters and the cops start to figure out they have rats in their organizations—the tension ratchets up and emotions boil over, leading to a bloodbath climax of Shakespearean proportions.

As Costello, Nicholson is clearly in his element—his performance goes a long way toward helping me forget uncomfortably self-conscious attempts to reinvent himself like About Schmidt. Costello oozes both hedonistic charm and cool menace, qualities that Nicholson innately possesses. At the same time, there’s a real risk that he might come off as silly, as in a scene where he’s scaring the shit out of Costigan by quoting John Lennon and gesturing with a hand—not his own, but the severed limb of an enemy, which he nonchalantly pulls out of a plastic bag. Or in another scene where he meets Sullivan in an empty porn theatre and surprises him by whipping out a huge dildo (this scene wasn’t actually scripted; Nicholson suggested it himself).

But Scorsese is a master of knowing how much rope to give his actors. For every scene of lunatic humor, the director’s sure hand is there controlling the tone and bringing out the characters’ darker sides: In an early part of the film, Costello is generously handing out money to kids, but in the next scene, we see a flashback of him blowing someone’s head off on a South Shore beach. Later, we cut from a shot of him enjoying an opera to a shot of him being full-on crazy in a bizarrely decadent cocaine-fueled threesome.

As Southie cop Sullivan, Matt Damon is, of course, right at home. We see him moving up the ranks of the State Police and bantering jovially with his cohorts. When the firemen beat the police in a game of football and are suddenly surrounded by women, Sullivan quips: “Firemen getting pussy—the first time that’s ever happened in the history of firemen, and the history of pussy.” He reveals his evil side to the audience mostly through his relationship with Costello and his betrayal of his fellow police officers. Eventually, his immorality catches up with him and spills over into his love life, as Madolyn begins to realize he’s not the perfect guy she thought he was. Meanwhile, she starts falling for one of her patients—the passionate Billy Costigan.

DiCaprio—who worked with Scorsese in 2002’s Gangs of New York and 2004’s The Aviator—surprises with the all-out ferocity of his role as Costigan. In order to convince Costello that he’s not a cop, he goes around breaking bottles on gangsters’ heads and getting the crap beat out of himself. It’s almost too much; I found it difficult to accept his character’s motivation to take that kind of shit—just being a good cop didn’t seem to be explanation enough.

The element that makes The Departed truly stand out is the streak of razor-edged humor that runs throughout the film, alternating with the violence to take you on a giddy, schizophrenic thrill ride. For instance, the ridiculous overkill profanity that comes pouring out of the mouths of Sergeant Dignam (Mark Wahlberg) and FBI Captain Ellerby (Alec Baldwin) is funnier than most of the so-called comedies I’ve seen lately.

Taking on such a huge project in this city strangled by traffic and Teamsters seems like a leap of faith for Scorsese. He’s drawn his cinematic identity from the romance and tragedy of the streets of the Big Apple, yet he has effectively brought to life the brutal underground Irish mythology of Southie. That he accomplishes it with such clear-eyed attention to detail shows his boundless professionalism. It’s a unique, stylized view of our city (the misty, neon Chinatown sequences look like something out of Blade Runner), and he serves it up without losing his distinctively gritty personality. He’s made another excellent Scorsese film, but lots of those exist—what’s most impressive is that he’s pulled off the rare feat of making a great Boston film.


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