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100 Greatest Gangster Films: The Departed, #7

100 Greatest Gangster Films: The Departed, #7 1


100 Greatest Gangster Films: The Departed, #7


Where to begin?

Nicholson is diabolically brilliant as Boston mob boss Frank Costello.

Leonardo DiCaprio shows acting chops that he had only hinted at in earlier films as the troubled undercover cop Billy Costigan.

Matt Damon is perfectly cast as Colin Sullivan, the seemingly altar boy detective who is the mob mole inside the Massachusetts State Police.

And Mark Wahlberg, Martin Sheen, Alec Baldwin and the rest of the stellar cast make the most of whatever screen time is given them.

This is just a damn good movie, certainly one of the best of the decade and arguably one of the best of all time.

It won four Oscars, including Best Director, an award that had long eluded Martin Scorsese. It also was the first movie based on a foreign film (the Hong Kong gangland thriller Infernal Affairs) to win for Best Picture.

Scorsese and screenwriter William Monahan took the outline of Infernal Affairs, grafted it onto actual events that had taken place in the New England underworld and delivered a classic. Their writing and directing do for the Irish underworld of Boston what Francis Ford Coppola and Mario Puzo did for the Italian underworld of New York three decades earlier. Like The Godfather, The Departed defines a time, a place and a subculture.

Writing for the Boston Globe, Ty Burr said The Departed is “the closest we’ve come yet to The Great Boston Movie, a beast that requires more honesty than filmmakers (and audiences) have been willing to grant.”

Scorsese opens his story with news clips from the turbulent 1970s and the school busing riots that helped give Boston its reputation for racial intolerance and polarization. Against that backdrop, we see Frank Costello in a corner store offering a young boy a handout—paying for groceries that the boy and his family obviously are hard-pressed to afford.

The boy is Colin Sullivan. The act of kindness is Costello’s first recruitment pitch. He throws in a comic book for good measure as the boy’s eyes light up.

Then, in the first of what seems like an endless stream of comments and one-liners that perfectly define his character, Costello asks the boy, “You do good in school?”

When Sullivan replies that he does, Costello grins (and here Nicholson offers one of those eye rolls that say so much more than the dialogue) and says, “I did too. They call it a paradox.”

We get nearly 20 minutes of action before the opening credits roll and by that point the movie is off and running, a nonstop roller-coaster ride of lies, betrayal and double-dealing on the streets and inside police headquarters. Infused with equal parts cynicism and pessimism (stereotypical traits of the Irish-American experience, we’re told), the dialogue is crisp, erudite and profane.

There are references to Hawthorne, Shakespeare and James Joyce. Conversely, and while we didn’t keep count, the IMDb website notes that the film also includes 237 uses of the word “fuck” or its derivatives. According to IMDb, that’s the most ever in a film that won the Best Picture Oscar.

There is a foray into Latin, when Baldwin’s Capt. Ellerby tries to get at the motive behind a gangland hit.

“Que bono?” he asks Sullivan. “Who benefits?”

“Que gives a shit?” replies the detective, in dead-on accurate police speak.

There is also a reference, although not entirely accurate, to Freud’s take on the Irish as “the only people who are impervious to analysis.”

Scorsese used the alias of famous Italian-American gangster Frank Costello (born Francesco Castiglia) for Nicholson’s character, but there is no doubt that he is the cinematic version of James “Whitey” Bulger, the notorious Irish mob boss from South Boston who terrorized the city for years. Bulger dealt in drugs, gambling, extortion, prostitution and murder. And on occasion, he ran guns for the IRA to enhance his stature in the poorer Irish neighborhoods of the city.

His brother William Bulger was, at different times, the President of the Massachusetts State Senate and the University of Massachusetts. Whitey clearly went in a different direction. But he managed to bob and weave in a violent underworld for three decades. Only later did it become clear that he had a get-out-of-jail card.

Bulger was a “top echelon” informant for the FBI, the highest and most secret rank of federal snitch. For years, he provided information about underworld rivals, helping the Feds make dozens of cases, most against traditional La Cosa Nostra gangsters. In exchange, two rogue FBI agents who were wined and dined by Bulger fed him the names of underworld figures who were providing law enforcement with information about him.

Some of those people turned up dead.

Both FBI agents were implicated in a criminal conspiracy. One is now serving a lengthy prison sentence. It was not the finest hour for the agency J. Edgar Hoover built.

That back story supports one of the best of many great lines in the movie. Wahlberg’s Staff Sgt. Dignam is at a meeting with various law enforcement agencies who have set up a task force to go after Costello. Of the FBI, Dignam says, “My theory is . . . treat ’em like mushrooms. Feed ’em shit and keep ’em in the dark.”

Whitey Bulger, who disappeared in 1995 shortly before he was indicted on federal racketeering and murder charges, spent nearly 16 years “in the wind” before being captured in Los Angeles in the summer of 2011. Bulger was on the FBI’s 10 Most Wanted list for more than a decade and there were those who believed the feds weren’t really interested in bringing him to justice because of the stories he could tell about the FBI’s role in his criminal activities.

Some of the story has already surfaced and it’s not pretty, although it is sometimes humorous. Much of it is detailed in a 600-page report filed by a federal judge assigned to get to the bottom of the FBI-Bulger relationship. There have also been several books written about it. The best one, for our money, is Black Mass.

One anecdote from real life could have been a scene in the movie: In 1985, the DEA had hidden electronic listening devices in Bulger’s car.

He learned about them (presumably from the FBI) and ripped them out. The DEA guys were listening when it happened and hightailed it over to Bulger’s garage. At the very least, they wanted their expensive equipment—valued at about $20,000—returned.

Bulger was happy to give them their bugs, but was curious about what they were up to, telling them, “We’re all good guys here. You’re the good good guys and we’re the bad good guys.”

Costello’s secret in The Departed is that he, too, is an FBI informant. That information changes the dynamic of the cat-and-mouse game that starts when Sullivan and Costigan begin their undercover work.

Matt Damon’s Sullivan, a pristine State Police academy graduate, feeds Costello information from inside law enforcement, referring to him as “Dad” whenever he calls on a cell phone.

Meanwhile, DiCaprio’s character Costigan is recruited by Capt. Queenan (Martin Sheen) and Sgt. Dignam from the same graduating class and goes undercover after he is bounced from the State Police and jailed on a trumped-up aggravated assault charge.

Queenan, in turn, becomes a father figure to the angry, young cop who struggles to make sense of law enforcement, the underworld and his place in all of it.

Playing the role of a hothead with a short temper, DiCaprio works his way into Costello’s organization at the same time Sullivan moves up the State Police ladder to a position in the organized crime investigating unit.

Eventually, both sides learn that the other has someone inside. The second half of the movie—full of dropping bodies, one literally from the roof of an abandoned warehouse, the rest falling under the constant spray of bullets—spins around the frantic attempts by Sullivan and Costigan to ferret out the identity of their counterpart.

Both also share a love interest in Madolyn (Vera Farmiga), a police shrink that Costigan is seeing as part of a court-ordered psychiatric evaluation after he is jailed on those phony charges. She eventually becomes the only person that Costigan can trust and indirectly sets up the movie’s brutally cold, but satisfying, finale.

Through it all, Costello continues a dizzying commentary as he moves from one underworld gambit to the next, dealing stolen, high-tech microchip processors to the Chinese, moving shipments of cocaine, dismembering bodies and gunning down associates.

“She fell funny,” he says offhandedly of a female victim after shooting her in the back of the head as she is kneeling in a field.

There are glimmers of humanity in Nicholson’s character, as when he asks an associate about the man’s ailing mother.

“She’s on her way out,” the associate sadly replies.

But then, returning to form, Costello replies, “We all are. . . . Act accordingly.”

Whether he’s sprinkling cocaine over two prostitutes with whom he is frolicking or berating a pedophile priest in a neighborhood restaurant, Costello is always in motion and constantly taking things to their limit. He is not immoral, but rather amoral, a mob boss who’s chosen a life where good and evil no longer seem to matter.

“No one gives it to you, you have to take it,” he says in a voice-over in which he decries the lack of initiative on the part of people looking for handouts and good will during the busing riots.

“A man makes his own way,” he says at another point.

And, in perhaps his most telling and cynical take on the choice between good and evil, he asks rhetorically, “When you’re facing a loaded gun, what’s the difference?”

Costigan, Sullivan, Queenan, Ellerby, Dignam and the rest of the cops and gangsters all seem to share a version of that philosophy.

There are plenty of loaded guns in The Departed and just as many twisted and complex characters.

HIT: The interdepartmental rivalries that undermine the investigation of Costello are based on fact. For years, organized crime figures benefitted from disorganized law enforcement. There’s a lot of that here, separate and apart from the fact that Sullivan is a mole. Again, Dignam nails it. When a surveillance operation goes bad, he gets into a shouting match with a detective from another agency, each asking whom the other thinks he is.

“I’m the guy doing his job,” Dignam screams. “You must be the other guy.”

MISS: It’s hard to find anything not to like. But if we must, the final scene with the rat walking across the balcony railing outside Sullivan’s apartment with the dome of the Massachusetts State House in the background was a bit much. It was unnecessary symbolism. We get it.

REALITY CHECK: Over the years, Whitey Bulger “sightings” have been reported throughout the Western Hemisphere. At one point, he was “spotted” in Ireland (makes sense). At another, in Sicily (go figure). But the best was a report that he was seen walking out of a movie theater in Seattle. The film playing that night was The Departed.

BEST LINE: There are so many that it’s hard to pick one. We’ll go with Frank Costello’s (Nicholson’s) opening lines, “I don’t want to be a product of my environment. I want my environment to be a product of me.”

WHAT THEY WROTE AT THE TIME: “All the actors bring their A games to this triumphant bruiser of a film, its darkly wanton wit the only defense against complete chaos.”—Peter Travers, Rolling Stone

CASTING CALL: Both Ray Liotta and Denis Leary were considered for the role of Dignam, but each had prior commitments. Robert De Niro turned down the role of Queenan to appear in The Good Shepherd, a movie that DiCaprio dropped out of to play Billy Costigan here.

GOOF: There’s a brief scene in which a suburban police car drives by as the bodies of two mobsters are discovered. The police cruiser is marked with the words “Lynne Police.” There is no “e” in Lynn, Massachusetts—the Boston suburb that is referenced.

REPEATED WATCHING QUOTIENT: This should be an annual event for anyone who enjoys the genre. The writing, the acting and the directing all shine and get better with each viewing.

BET YOU DIDN’T KNOW: Nicholson, a staunch New York Yankees fan, refused to wear a Boston Red Sox cap for the film.

BODY COUNT: Twenty-two.


Join us as we count down the greatest gangster movies of all time! Click here to see what you’ve missed so far.

[Reprinted from The Ultimate Book of Gangster Movies by George Anastasia and Glen Macnow. Available from Running Press, a member of The Perseus Books Group. Copyright © 2011.]

The Ultimate Book of Gangster Movies

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George Anastasia is a crime reporter for the "Philadelphia Inquirer" and author of several books, including "Blood and Honor" which Jimmy Breslin called "the best gangster book ever written." Glen Macnow was a writer for the "Philadelphia Inquirer" and "Detroit Free Press." He is currently a talk-radio host on 610-WIP in Philadelphia. George and Glen have co-authored "The Ultimate Book of Gangster Movies."

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