20 Years Ago Today: Matt Damon Starred In A Legendary Director's Oscar-winning Crime Thriller

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Martin Scorsese's 2006 crime drama "The Departed" — released 20 years ago today — was based on the 2002 Hong Kong film "Infernal Affairs," directed by Alan Mau and Andrew Mak, although Scorsese's movie is certainly the more popular and celebrated of the two. It's a little unusual that "The Departed" scored Scorsese his first Oscar for Best Director, as the film was less ambitious than some of his previous movies. Indeed, Scorsese had previously received Best Director Oscar nods for "Raging Bull," "The Last Temptation of Christ," "GoodFellas," "Gangs of New York," and "The Aviator," and while the relative quality and artistic success of those movies can be debated, one might note that "The Departed" was more a "return to the well" moment for Scorsese than a bold new vision.

This is the same reason why "The Departed" usually doesn't land all that high on your average ranking of Scorsese's movies. In point of fact, many people feel that Scorsese's Oscar for "The Departed" was a make-good gesture by the Academy to give the director his due, even if the film he was awarded for is rarely considered his best.

The premise of "The Departed" is at least novel. Matt Damon plays Colin Sullivan, a Boston street kid who was groomed from an early age to admire and serve the criminal empire of one Frank Costello (Jack Nicholson). Sullivan grows up and manages to get a job with the Boston PD, specifically to serve as Costello's informant. Meanwhile, Boston cop Billy Costigan (Leonardo DiCaprio) goes undercover as a criminal, hoping to get the dirt on Frank. Both Sullivan and Costigan know there's a mole in their respective ranks, but they initially don't know who it is.

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Martin Scorsese often makes films about criminals and amoral people, as he is clearly fascinated by sociopathy. He is a moral filmmaker who takes long, hard looks at bad people, mapping out the ripples their wicked behavior leaves in the universe. Some have accused Scorsese of glorifying his criminal characters, as he is always careful to show how exciting it is to flout rules, take drugs, and party like there are no consequences. Of course, those who make those accusations have apparently never watched the third act of any Scorsese movies, in which said criminals see their lives fall to pieces.

"The Departed" makes Scorsese's morality clearer by depicting two characters who skip across the moral line, one from each direction. Sullivan enjoys both the privileges of being a cop and the benefits of being a paid stooge for a super-criminal. Matt Damon is perfect in the role, as his fresh-faced handsomeness and dazzling confidence can handily mask the sociopathy lurking underneath. Meanwhile, the Costigan character has a rougher time of things, as pretending to be a criminal erodes his soul. Committing and witnessing brazen criminality hollows him out, and he has to regularly visit the local police psychiatrist, Vera Farmiga's Dr. Madolyn Madden, for the sake of his mental health. It should be stated that Costigan, to avoid legal complications, isn't employed by the police during his time undercover, and only a few people know his secret. He is truly alone. Also, in a contrivance that no one really likes, Madden begins dating Sullivan.

"The Departed" features some standout roles for the likes of Mark Wahlberg and Alec Baldwin as well, with the pair playing higher-ups in the Boston police department. Baldwin's scattershot, vulgar speech about cigarettes, in particular, is a highlight.

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"The Departed" was nominated for five Academy Awards and won four, including Best Picture, Best Director, Best Adapted Screenplay, and Best Editing. It's since become deeply beloved by a certain type of film-bro, as evidenced by it being rated the 40th best movie of all time on IMDb's top 250 movies list. Many college dorm rooms likely had a poster for "The Departed" in them in the mid-2000s.

For my money, Martin Scorsese's more recent movies have delved into the moral turpitude of the human heart far more deeply and effectively than his earlier work. I maintain that post-"Departed" Scorsese films like "The Wolf of Wall Street," "Silence," and "Killers of the Flower Moon" are better than "The Departed" or even beloved titles like "GoodFellas" and "Casino." (I've similarly argued that "Killers of the Flower Moon" is the good version of "Gangs of New York.") "The Departed" certainly covers Scorsese's interests about the moral failures of the criminal mind, but it's very up-front about its themes, wearing its ideas on its sleeve.

No matter where you rank "The Departed" on your personal list of Scorsese movies, it's certainly an entertaining watch. It's hard-boiled and slick, and the soundtrack is fun. (Just ignore the fact that Scorsese reuses the Rolling Stones' "Gimme Shelter," which he had also used in "GoodFellas" and "Casino.") It sports a violent and tragic ending befitting the material to boot, with certain characters proving to be unexpected turncoats. All in all, it's a solid movie that powers through its 151 minute runtime at a breakneck pace. It's a very good flick.