Matt Damon’s Most Violent R-Rated Thriller Officially Leaves Streaming After 20th Anniversary

Matt Damon has that unique clean-cut charm that comes in handy when he plays charming and roguish heroes. But it can be a nasty and useful asset when he is a bad guy, too. In this crime thriller directed by Martin Scorsese, Damon essays a corrupt cop who has built an impressive career by quickly rising through the ranks. But that is not because of any innate talent. He became an officer only because he is sponsored, so to speak, by a mob boss.

The crime thriller movie was rated R and is one of the most violent movies in Damon’s career, if not the most violent. It also featured Leonardo DiCaprio and Jack Nicholson in lead roles alongside Damon. Both Damon and DiCaprio play informants, only on opposite sides. The movie was an American remake of the 2002 Hong Kong action thriller Infernal Affairs.

The Departed Leaves HBO Max on November 1

Matt Damon as Colin Sullivan in The Departed | Credits: Warner Bros. Pictures

The movie in question is The Departed. It is leaving HBO Max in the United States on November 1, 2026. Released theatrically on October 6, 2006, the film recently crossed its 20-year milestone earlier this month. The cast is otherwise, as well, packed with compelling performances. The ensemble also includes Mark Wahlberg, Martin Sheen, Vera Farmiga, Alec Baldwin, and Ray Winstone.

Damon essays the role of Colin Sullivan. Sullivan is a high-ranking Massachusetts State Police officer. But he is secretly working for terrifying, mercurial Boston mob boss Frank Costello (Nicholson). Meanwhile, Billy Costigan (DiCaprio) is an undercover cop who has infiltrated Costello’s organization. But his position is precarious, as Costello is a little too good at reading people, and it is only a matter of time before he figures out that Costigan is actually a straight shooter. Eventually, both sides discover they have a mole.

The better Colin becomes at his police job, the more useful he is to Costello. But the situation is different for Billy. The deeper he penetrates the criminal organization, the more exposed he becomes to the man feeding it police intelligence.

The film won four Oscars, and got Scorsese his first Best Director Oscar, if you can believe it. It also won Best Picture, Best Adapted Screenplay, and Best Film Editing. It is strange that this particularly vicious thriller became a landmark in Scorsese’s glorious career. It is certainly one of Scorsese’s best movies.

Martin Scorsese Thought the Film Was Too Violent for Awards Season

Scorsese, however, had little expectation that The Departed would become an awards favorite. Frequent Scorsese collaborator and producer Emma Tillinger Koskoff recalled that, although he was proud of the film, he considered it too violent and vile for the Academy to embrace. She said (via TheWrap):

It is indeed ironic, and yet Scorsese’s apprehension made sense. It was violent even by his standards. And more than that, its violence was abrupt and ugly. It was also often stripped of ceremony. Slightly spoilery, but major characters are killed unceremoniously. And they hit the audience like a truck. They have, after all, spent a couple of hours with them. This is not unusual for this Scorsese movie. But somehow, The Departed‘s ending hits harder than most Scorsese movies in that walloping manner, except maybe Goodfellas. He gives their schemes elaborate attention and their lives frighteningly little protection.

Damon’s Colin Sullivan embodies that nastiness. His badge and polished manners help him thrive while he betrays colleagues who trust him. As exposure becomes more likely, preserving his respectable life means putting other people’s lives at risk.

Does The Departed feature Matt Damon’s best performance? Or his work in The Odyssey outdid Sullivan? Share your thoughts in the comments.