The pivotal acting lesson Matt Damon learned from Jack Nicholson: “That’s not what I did”

Matt Damon and Jack Nicholson co-starred in the 2006 crime thriller The Departed, opposite Leonardo DiCaprio and directed by Martin Scorsese. The film is a remake of the 2002 Hong Kong movie Infernal Affairs by Andrew Lau (not to be confused with the 1990 Richard Gere movie, which barely got made, let alone remade) and is loosely based on real events involving Boston’s Winter Hill Gang.

As to the film in question, Nicholson plays an Irish mob boss Frank Costello, who plants Colin Sullivan (played by Damon) as a mole within the Massachusetts State Police. Simultaneously, the police assign undercover officer Billy Costigan (Leonardo DiCaprio) to infiltrate Costello’s organization. As both sides become aware of the infiltration, Sullivan and Costigan compete to expose one another as Costello pulls their strings.

Aside from Nicholson, DiCaprio and Damon, the movie boasts so many stars as the night sky, having performances from Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga, and Alec Baldwin in supporting roles. Robert De Niro turned it down, though.

Despite De Niro having better things to do than a Scorsese picture (for once), The Departed received critical acclaim across the board and won four Academy Awards, including ‘Best Picture’ and ‘Best Director’ for Scorsese, his only one in the category to date.

They missed out on most of the actor awards, but there wasn’t a performance in the film that was unpraised. Andy Lau thought his progenitor was superior but still had kind words about Scorsese’s version, saying, “Of course, I think the version I made is better, but the Hollywood version is pretty good too. [Scorsese] made the Hollywood version more attuned to American culture.”

Speaking to The New York Times, Damon says “Jack looked at that scene” — and, the interviewer says it was “startling” how Damon inhabited “Nicholson’s disquieting energy”—saying “and he goes: ‘What I did was I made the person being executed a woman. That’s sinister. Costello executes a guy in a marsh? We’ve seen that kind of scene in movies before. That’s not what I did.’” And gangster movies (movies in general, really) are no stranger to killing off female characters. But Damon found this choice significant.

Born on October 8th, 1970, in Cambridge, Massachusetts, Matt Damon began his acting career with a minor role in 1988’s Mystic Pizza. His breakthrough came with 1997’s Good Will Hunting, a film he co-wrote and starred in alongside Ben Affleck. The movie earned them the Academy Award for ‘Best Original Screenplay’, and Damon received a nomination for ‘Best Actor’.

Looking ahead, Damon is set to star as Odysseus in Christopher Nolan’s upcoming film of Homer’s epic poem The Odyssey, scheduled for release in 2026. One can only hope that this adaptation is quite so successful. Leo is starring in a Paul Thomas Anderson film called One Battle After Another, which we know very little about, and Jack Nicholson unlaced his gloves in 2010. It’s unlikely we’ll see him again, but The Departed is worth a rewatch if you miss the guy.

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