Honestly, it is still hard to believe that The Departed is the only movie where Martin Scorsese actually won Best Director. You'd think the guy who made Goodfellas and Raging Bull would have a shelf full of them, but nope. It took a gritty, loud, and incredibly foul-mouthed South Boston crime saga to finally get the Academy to cave. At the center of that 2006 whirlwind was a first-time (and only-time) pairing that movie fans had been begging for: the veteran chaos of Jack Nicholson and the calculated, "golden boy" intensity of Matt Damon.
People call it a remake. Technically, they aren't wrong. It’s based on the Hong Kong thriller Infernal Affairs, but if you’ve seen both, you know they feel like entirely different animals. While the original is a sleek, existential ballet, the jack nicholson and matt damon movie is a sweaty, claustrophobic nightmare about identity and rats. It’s essentially a $90 million "B-movie" as Scorsese himself once joked.
The Wild Reality of Working with Jack Nicholson
When Jack Nicholson signed on to play Frank Costello, he didn't just show up and read lines. That’s not how Jack works. He basically looked at the script and decided it was a bit too "tame." He wanted Costello to be more than just a mob boss; he wanted him to be a force of nature.
Matt Damon has told this story a million times on podcasts, and it never gets old. He recalls getting a call from "Marty the Director" (Scorsese always introduces himself that way, which is kind of hilarious) saying that Jack had "some ideas."
Those ideas?
They usually involved making the scenes way more uncomfortable. In that infamous porno theater scene, Nicholson decided on a whim to wear a prop dildo to shock Damon. He wanted to see a real reaction. He wanted the audience to feel the unpredictable, flickering fuse of a man who had completely lost his moral compass.
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Why the Red Sox Cap Mattered (To Everyone But Jack)
If you know Boston, you know the Red Sox are a religion. The real-life inspiration for Frank Costello was Whitey Bulger, a man who famously wore a Red Sox cap everywhere. It was a staple. Naturally, the wardrobe department handed Jack a Sox hat.
He refused. Point blank.
Nicholson is a die-hard Yankees fan. He’s a New Jersey kid at heart, and he told the producers he wouldn’t wear that "B" on his head for any amount of money. In the end, Costello wears a Yankees cap in the heart of Southie. It’s a detail that would get a real mobster killed in five minutes, but because it’s Jack Nicholson, we all just sort of roll with it.
Matt Damon and the "Anti-Action" Hero
While Jack was busy being a human hurricane, Matt Damon was doing something much more subtle and, frankly, much harder. He played Colin Sullivan, the mole inside the Special Investigations Unit. Sullivan is a guy who has spent his whole life pretending to be the hero while serving a monster.
Damon made a very specific choice for this role. Most actors in a Scorsese flick want to look tough. They want to be the guy throwing the punches. Damon went the other way. He told Scorsese he wanted Sullivan to be a guy who loses every fight he’s in. He wanted his character to be physically incapable of performing under pressure—to the point where he even suggested Sullivan suffer from sexual dysfunction because of the crushing weight of his double life.
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It makes the character pathetic. You almost feel bad for him until you remember he’s a cold-blooded traitor.
The Real History Behind the Roles
- Frank Costello (Nicholson): Heavily modeled after James "Whitey" Bulger, the leader of the Winter Hill Gang.
- Colin Sullivan (Damon): Partly inspired by John Connolly, the FBI agent who grew up with Bulger and ended up protecting him for years.
- Billy Costigan (DiCaprio): The "mirror" to Damon’s character, the cop pretending to be a criminal.
The movie is a giant web of people pretending to be something they aren't. It’s why the ending is so sudden and violent. There’s no "closure" in the traditional sense because, as Scorsese said, it's "Moral Ground Zero." Everyone is compromised. Everyone is a rat.
Why The Departed Still Holds Up in 2026
A lot of people think The Departed won its Oscars because the Academy felt bad for snubbing Scorsese for thirty years. Maybe. But rewatching it today, the film feels surprisingly modern. The editing by Thelma Schoonmaker is jagged and fast, almost like a precursor to the way we consume media now.
It doesn't waste time.
The dialogue is also legendary. William Monahan, the screenwriter, grew up in Boston, and he captured that specific brand of "smart-aleck" hostility that defines the city's streets. Whether it's Mark Wahlberg screaming about "depah-ted" souls or Alec Baldwin losing his mind over surveillance, the movie has a rhythm that few crime films have ever matched.
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Is It Better Than Infernal Affairs?
This is the big debate. If you’re a purist, you probably prefer the Hong Kong original. It’s more poetic. But the jack nicholson and matt damon movie is a different beast entirely. It’s about the decay of a city. It’s about the specific Irish-Catholic guilt that haunts the characters.
One isn't necessarily "better," but the American version is certainly louder. It’s a movie that demands you pay attention to every side eye and every whispered phone call.
What You Should Do Next
If you haven't seen the film in a few years, it is worth a rewatch just to track the "X" marks. Scorsese hid an "X" in the frame—on windows, in the background, or even on the floor—every single time a character is about to die. It’s a direct homage to the 1932 version of Scarface.
For those who want to dive deeper into the real story, check out the documentary Whitey: United States of America v. James J. Bulger. It shows just how close Nicholson’s performance was to the real-life terror that gripped Boston for decades.
Finally, if you’re a fan of the "mole" subgenre, go back and watch Infernal Affairs. Seeing the DNA of The Departed in a totally different cultural context is a masterclass in how stories can be translated and transformed.