This Matt Damon Crime Movie Is Considered One Of The Best Of The 21st Century

In June of 2025, The New York Times released an ambitious list chronicling the best movies released since January 1, 2000 — marking the best 100 movies of the 21st century so far. If you're familiar with great films from the past 25 years, you're probably not all that surprised that the 2007 best picture winner at the Academy Awards, "The Departed," which stars Matt Damon and a whole host of other A-list performers, is on the list. In fact, it's number 31 on the ranking.

"The cat-and-rat gangster picture that finally won Martin Scorsese his Oscar happens to be one of the most downright entertaining of the century," the outlet writes, acknowledging the frankly ridiculous fact that Scorsese hadn't won an Oscar for directing before that same ceremony in 2007. "Scorsese takes the Hong Kong flick 'Infernal Affairs' and plops it in Boston, Dropkick Murphys soundtrack and all," the reasoning for the ranking continues before shouting out the movie's unbelievable cast. On one side of the law there's Leonardo DiCaprio's rough-around-the-edges cop posing as a criminal. On the other there's Matt Damon's golden-boy police officer working for the Mafia. In the middle there's Jack Nicholson's Irish mob boss, smiling like the Cheshire Cat. Let the games begin."

"It's a film so deeply packed with ideas that there is no way your mind can drift anywhere but inside the film," director Josh Safdie, who included "The Departed" on his personal ballot, wrote for the Times. "Oh, and it's got a polarizing ending that might also be one of the best of all time." Okay, so what about that ending? Also, who does Damon play in "The Departed," in case you forgot who's doing what in this beautifully chaotic crime drama? (Oh, just in case: spoilers lie ahead!)

As you may have gathered from The New York Times' description of "The Departed," this is a classic Martin Scorsese mob movie, and a lot of the intrigue happens to center around Matt Damon's double agent Colin Sullivan. (Also, it's based on the Hong Kong crime thriller "Infernal Affairs" as well as some real-life stories of Boston gangsters, in case you're wondering what inspired Scorsese.) We learn early on that, as a kid, Colin crossed paths with mob boss Frank Costello (a sneering, sinister Jack Nicholson), who took the young boy under his wing. 

As an adult, Colin is a staff sergeant with the Massachusetts State Police in their Special Investigations Unit, which ultimately gives Frank a rock-solid mole within the department. Unbeknownst to Colin and Frank, though, the unit's captain Oliver "Charlie" Queenan (Martin Sheen) and its other staff sergeant Sean Dignam (Mark Wahlberg) enlist one of Colin's fellow cadets at the police academy, Billy Costigan (Leonardo DiCaprio), to infiltrate Frank's organization. 

Without directly spoiling the ending just in case you haven't caught "The Departed" in the years since it came out — and I strongly urge you to fix that, if that is the case — I'll just say that Scorsese's typical fluid morality comes into play in a frankly enormous way at the movie's conclusion, particularly after bodies start to pile up like crazy. 

The brilliance of "The Departed," and one of the many reasons that it richly deserves a spot in the top 50 of the Times' 100 best movies since 2000, is that you're never entirely sure who you should root for, and at various points, your own allegiances shift as the characters make increasingly cruel and dangerous decisions. I don't need to necessarily do a deep dive on why a Scorsese movie about the Boston mob is great, even though I could; those words alone are kind of self-explanatory. Instead, let's focus on Damon, who more than holds his own against some of the greatest living actors (and Oscar winners like Nicholson and DiCaprio, though the latter hadn't won his yet — a feat Damon has, surprisingly, not yet achieved).

Let me start by saying I know that, throughout his career, Matt Damon has taken on roles that fall into the category of "slimy jerk." For one, there's "The Talented Mr. Ripley," and years after his turn in "The Departed," he provided audiences with some heel turns in "Interstellar" and "The Last Duel," just to name a few. Still, "The Departed" is a particularly odious role for Damon, and that's why it's one of his all-time best performances.

Don't be distracted by Jack Nicholson's powerful and terrifying performance as Frank or Leonardo DiCaprio's twitchy Billy, who always seems to be hanging on by a thread. Focus on Damon's Colin, because he's the narrative glue that holds "The Departed" together. By choosing Colin as his protégé, Frank ensures that he becomes a father figure to a vulnerable young man, which, if you're a cynic like me, points to the fact that Frank is always thinking two steps ahead (because, once Colin joins the MSP, he can serve as Frank's mole). Colin presents himself as an upstanding man and detective to both his squad and Madolyn, but that's what makes him so insidious. He is, to use the film's parlance, an absolute rat who only cares about his own status and safety, and without getting into specifics — again, in case you get to experience this movie for the first time — he'll throw absolutely anybody under the bus to save his own skin, including Frank, the closest thing he has to a father. 

When Colin gets his comeuppance, it feels both richly deserved and somehow sort of wrong, because, alongside Billy, he's ostensibly one of the movie's protagonists. Still, if you fully realize exactly how, to use my own adjective, "slimy" Colin is throughout the entire movie, he has the potential to make your skin crawl, and that's a great role for Damon, a guy whose public image and general affability can sometimes trick audiences into siding with him. He's phenomenal in this movie, and he's just one of many reasons to watch it.

"The Departed" is amazing, and if you haven't seen it, you should absolutely remedy that (and consider the rest of the Times' list, which includes some real gems).