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Best Picture Series — The Departed (2006) Review

12/31/2025

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Evan D.

Picture
As a project this year we are taking a trip through time to revisit all of the Best Picture winners in history, Wings to Anora. The Departed is the eightieth film in that series, to see all the other Best Picture reviews, click here.
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Early 2000s Boston and the State Police still can’t pin down charges on Frank Costello (a truly quintessential Jack Nicholson,) a gang leader that’s terrorized the city for decades. Costello has groomed Colin Sullivan (Matt Damon) to be his mole in the police force, reporting back on planned operations against the gang. At the same time Sullivan is rising the ranks of the Staties, police captain Queenan (Martin Sheen) plant undercover officer Billy Costigan (Leonardo DiCaprio) as a rat inside Costello’s crew. When an operation goes sideways, both the police and Costello begin a mad dash search for the informants within their organizations. 

Loosely a remake of the Korean Internal Affairs film series, Martin Scorsese’s only Best Picture winner to date is not merely another of the acclaimed director’s mafia flicks. The reflection of a mob informant against a police plant is a brilliant premise and one that neatly fits with the muddled morality that has always underpinned Scorsese’s best films. Costigan and Sullivan’s parallel descents into paranoia allow The Departed to dig even further into the psyche’s of a life of crime.

As is often the case in a Scorsese film, The Departed is tremendously entertaining. A film that delights in welcoming viewers into a world of debauchery and violence. Never fully condoning or admonishing characters, the movie tiptoes around the shadowy grey areas. What makes it work are the tremendous performances at its core. Nicholson, as always, is completely unhinged as the mafioso kingpin. Its an almost absurdist portrayal but he creates in the chaos an unpredictable center of gravity for the whole picture that keeps every scene he’s in on edge. DiCaprio, and to a lesser extent Damon, really nails the psychic toll of bending the soul. You can practically see on his face the cracks of someone who is being pushed to the edge. 

The Departed is among the great masterpieces of a director who has a stable of them. Like all the great films of the Scorsese oeuvre, he seduces audiences with the allure of the lives of these villainous people and then burns it all down. Goodfellas, The Wolf of Wall Street, Killers of the Flower Moon, just like The Departed these are admonishments of a system that let the unscrupulous take control of the world around them. But eventually the festering wounds at the center of these films become infected and their luxurious lives begin to rot out. A timeless perspective that this master of American cinema has revisited time and time again. 9/10
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