The Departed (2006)

We deal in deception here. What we do not deal in is self-deception.

–Captain Queenan (Martin Sheen)

Billy (Leonardo DiCaprio) is a goodhearted kid from South Boston who will ever feel out of place. He thinks he wants to be a cop. But as a preliminary academy training montage suggests, he knows both too much and too little to be at home among this self-proud crew. Sure, he resembles the majority of plebes with whom he shoots at targets and shouts “Sir yes sir,” but he’s also aware of how the world works, how place and background shape your options. As he acknowledges to his running partner Brown (Anthony Anderson), “You’re a black guy in Boston. You don’t need any help from me to be completely fucked.”

Billy comes in late at the start of The Departed, Martin Scorsese’s much anticipated return to brutal and brainy gangster-movie form. Before that, the streets of Billy’s childhood appear without him, punks fighting before a fast-panning camera under the Stones’ “Gimme Shelter,” while local kingpin Frank Costello (Jack Nicholson) looms over a couple of bodies and sums up his philosophy of place: “I don’t want to be a product of my environment. I want my environment to be a product of me.” Ruthless and large and, well, Jack Nicholson, Frank lumbers into joints where he’s owed protection money and expects every sort of respect. Spotting a girl behind the counter, he wonders whether she’s “had her period yet,” then whispers something pretty in her ear as he hands her cash (“Go buy some makeup”). Then he sees a boy, “Johnny Sullivan’s boy,” on a stool, puts money in his pocket, and asks if he does “good in school.” Yeah, him too, smirks Frank. “They call that a paradox.”

In Frank’s world, little Colin Sullivan (who grows up to be Matt Damon) is an opportunity. If Frank is too flamboyant to accommodate a “good in school” surface, he raises up Colin to be his boy, good in school, good in the academy, and good inside the Massachusetts State Troopers, where he rises quickly, privy to investigations and information that allow him to keep Frank apprised of the cops’ comings and goings. In turn, the Troopers’ Captain Queenan (Martin Sheen) and Sergeant Dignam (a supremely entertaining Mark Wahlberg) recruit their own mole, Billy, specifically by appealing to his lack of fit. “Do you wanna be a cop or do you wanna appear to be a cop?” they ask, cryptically, Billy squinting as his brain wheels turn. He wants to be a cop.

Though Queenan determines that for Billy, his family full of gangster, this means he must appear not to be a cop. He gets in a scuffle that lands him in prison, and when he emerges, he’s got a rep and a contact or two, including his raggedy heroin dealer cousin (Kevin Corrigan), enough to get him inside Frank’s gang. And so the terms are set: Colin and Billy are both rats, neither belonging to the world he inhabits on a daily basis. And yet both Colin and Billy might be described as “belonging” to the gangs that take them in, unknowingly, as rats. The gangs consist of colorfully manly men, including foul-mouthed, mostly disgruntled Captain Ellerby (Alec Baldwin) and Frank’s ferociously enthusiastic primary assassin, French (Ray Winstone). They embody old school values, where attrition is an inaccurate but handy measure of which side is up at a given moment.

Billy and Colin are a next generation, each troubled in his own way. Billy becomes increasingly paranoid, living too long undercover, wondering when the job will end (Queenan holds out for the major takedown, something about Frank running microchips for missiles). Billy’s apartment is cracked and confining, his conscience grinding, his participation in cruelties exhausting. Queenan has read him exactly right: the kid is lost, uncertain of his identity, and so he can pass between realms, not easily but urgently. Billy lives his confusion, popping pills, puking in trash barrels, taking unfathomable risks.

For his part, Colin initially enjoys the legit appearance, taking an upscale apartment he could never really afford on his salary, then becomes increasingly freakish about his illusory self-control, manifested at first in an appealing wit; he wins his fiancée, the sad-eyed police department therapist, Madolyn (Vera Farmiga), by seeming on top of his game and hers. He knows what she does, he says: “Guys talk to you about their feelings and whatnot.” Yet, despite his quick wit (“I saw a dead guy,” he calls from a crime scene. “I think I’m having post-traumatic stress. Can I see you for lunch?”), Colin is subtly disturbed, his anxiety plain and pedestrian. One morning in the kitchen, Madolyn invites him to “talk about last night.” “It’s all right,” she soothes. “Guys make too big a deal out of it.” Now, Colin can’t talk to her.

If it’s easy to see why Colin is loyal to the fearsome and charismatic Frank (who enquires after “that shrink cunt” who answers the phone at Colin’s apartment), Billy’s displacement is increasingly not enough to make him stick. Sent to discuss his schizzy existence with Madolyn, he finds in her a sympathy missing elsewhere. Though he can’t tell her who he is any more than Colin can, he breaks her heart: “Your vulnerability is really freaking me out right now. Is it real?”

This question of what’s real at any given moment is the crux of The Departed. For Colin and Billy, nothing can be real, and so it’s their capacities for living in no certain place determine their survival. While Madolyn’s dissimilar relationships with each mark their differences, her part is more plot-pointy than convincing: her sympathies tend to stand in for yours, as the movie doesn’t trust in the ethical and political ambiguities of the movie it remakes, Andrew Lau and Andy Mak’s brilliant Infernal Affairs (2002). (As if to underline her schematic function, Madolyn combines two women from the original film, bedding and counseling both men in order to connect and divide them.)

Rowdier and more neatly resolved than Infernal Affairs (that is, more “American”), The Departed grants Nicholson wide berth for jestering (see especially his rat imitation, as he worries about finding the spy, or his pronouncement on John Lennon: “The man could look at anything and make something out of it”). But his antics are not so compelling as the subtler work by both Damon and DiCaprio (who have plenty to live up to, as both Andy Lau and Tony Leung were precisely perfect in their film). As in the original, Billy and Colin’s doubled-and-different struggles are cleverly illustrated by surveillance and communications technology (cell phones, wires, lost signals) and editing that emphasizes their parallel tracks and near collisions (this film loses the first one’s most dazzling scene, a pursuit through hall- and alleyways as the two men leave a movie theater that remains one of the most elegant representations of self-and-other in any film, ever).

The Departed‘s understanding of identity is deeply rooted in place and culture — South Boston, Irish Catholicism, masculine rituals. As Colin turns increasingly cold-blooded, he also turns less anxious about who or why he is, able to commit the sort of brutality he once left to psycho-killers like Frank. Billy’s loss of faith in his mission and his homelessness leaves him only wanting only to “come in.” As divergent and well plotted as their paths seem, neither gets the shelter he needs.