When people talk about Martin Scorsese’s 2006 masterpiece The Departed, they usually start with Jack Nicholson’s over-the-top, dildo-waving performance or Leonardo DiCaprio’s sweat-soaked, anxiety-ridden portrayal of Billy Costigan. But honestly, the guy who holds the whole house of cards together is the one we’re supposed to hate.
Matt Damon.
Playing a villain is easy. Playing a "rat" who thinks he’s the hero of his own story? That’s where it gets complicated. In Matt Damon The Departed is essentially a masterclass in controlled sociopathy. While Leo gets the "showy" role—the undercover cop losing his mind—Damon has to play a man who has completely scrubbed his soul to fit into a suit.
The Boston Boy Who Went Inside
Damon didn't just show up and do a "Southie" accent. He grew up in Cambridge, so he already had the rhythm of the city in his blood. But for the role of Colin Sullivan, he went deeper. He actually shadowed the Massachusetts State Police on real-life drug raids.
Think about that for a second.
He’s a world-famous movie star sitting in the back of a tactical vehicle, wearing a bulletproof vest, watching guys kick down doors in Everett. He even admitted later that he didn't go in until the "all clear" was given—fair enough, he's an actor, not a commando—but he wanted to see how these guys carried themselves. How they stood. How they lied.
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The character of Sullivan is loosely based on John Connolly, the real-life FBI agent who was the handler for mob boss Whitey Bulger. Connolly ended up in prison because he became exactly what Sullivan is in the movie: a man who couldn't tell where the law ended and the crime began.
Why Sullivan is the Scariest Character in the Movie
Most movie villains have a "tell." They sneer, they have a facial scar, or they kick a dog. Sullivan doesn't. He’s the guy you want your daughter to marry. He’s got the penthouse overlooking the State House. He’s got the beautiful girlfriend. He’s the "golden boy" of the Special Investigations Unit.
But look at his eyes when he's alone.
There’s a scene where he’s watching the sunset from his balcony, looking at the golden dome of the Massachusetts State House. He doesn't look happy. He looks like he’s checking a receipt. He’s achieved the American Dream through a nightmare, and the stress of maintaining that facade is what makes his performance so subtle.
While DiCaprio is visibly falling apart, Damon is imploding. He’s a man who has to perform "honesty" every single day. If he slips up once, he’s dead. If he succeeds, he’s a hollow shell. It’s a lose-lose situation that he treats like a corporate promotion.
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The "Impotence" Debate and the Hidden Details
There’s been a lot of digital ink spilled over the years about Sullivan’s "issues" in the bedroom with Madolyn (Vera Farmiga). Some fans think it’s a hint that the character is a closeted homosexual—pointing to his over-the-top homophobic remarks as "protesting too much." Others think it’s just a physical manifestation of the crushing stress of being a double agent.
The truth is probably simpler: He’s a man who can’t connect with anyone because his entire identity is a fabrication.
You can't have true intimacy when you’re a mole. Every time he touches his girlfriend, he’s lying. That kind of psychological weight would make anyone "malfunction." It's a brilliant writing choice by William Monahan. It strips the "cool" away from the spy trope and shows the pathetic reality of living a lie.
What Most People Get Wrong About the Ending
The "rat" on the balcony at the end is a bit on the nose, sure. Scorsese has even taken some heat for how literal that metaphor was. But Sullivan’s death at the hands of Sergeant Dignam (Mark Wahlberg) isn't just a revenge kill. It’s the universe correcting a mistake.
Sullivan thought he could "clean" himself. He killed Costello. He erased Costigan’s files. He thought he could just... be a regular guy now. But in the world of Matt Damon The Departed, you don't get to just walk away.
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His final line, "Okay," is one of the most haunting moments in 2000s cinema. He isn't surprised. He isn't even really scared. He’s just... finished. The act is over.
If You're Rewatching Soon, Look for This:
- The "X" Factor: Scorsese hid "X" symbols in the frame (taped on windows, in the architecture) whenever a character was marked for death. Watch Sullivan’s scenes; the X's start appearing long before the finale.
- The Handshakes: Watch how Sullivan shakes hands. It’s firm, practiced, and utterly fake. He uses it like a weapon to disarm people.
- The Phone: Look at how he handles his burner phones compared to his work phone. The physical shift in his body language is subtle but definitely there.
How to Appreciate the Role Today
If you want to really "get" what Damon was doing, stop comparing him to the other actors. Don't look for the "acting." Look for the erasure of acting. Sullivan is a man trying to be the most boring, reliable guy in the room so nobody looks at him too closely.
It’s actually much harder to play "nothing" than it is to play "everything."
To truly dive into the lore of the film, you should check out the original Hong Kong trilogy Infernal Affairs. It gives you a whole new perspective on the Sullivan character (played there by Andy Lau). Also, if you’re into the true crime side of things, read up on the relationship between John Connolly and Whitey Bulger. It makes the movie feel 100% more terrifying when you realize the "mole in the state house" wasn't just a Hollywood invention.
Next Step: Watch the scene where Sullivan and Costigan talk on the phone for the first time without knowing who the other is. Pay attention to the silence. It’s the only moment in the movie where Sullivan is actually, briefly, himself.