Matt Damon’s Favorite Films Of All Time Come From The Most Legendary Directors

Some audiences might have first spotted Matt Damon during a notable dinner scene in Donald Petrie’s hit 1988 drama “Mystic Pizza.” Thereafter, Damon turned up as an extra in “Field of Dreams” and as one of the many handsome students in the 1992 boarding school thriller “School Ties,” both of them with his longtime friend and collaborator Ben Affleck. Damon went on to score some considerable screen time in Edward Zwick’s “Courage Under Fire” before delivering his first lead performance in 1997 in Francis Ford Coppola’s “The Rainmaker.” That same year, Damon and Affleck became acclaimed Academy darlings for writing and starring in Gus Van Sant’s “Good Will Hunting.” The pair won Oscars for their screenplay and have both been major Hollywood players since.

Damon, having gained the clout to be picky and the fame to be noticed, thereafter became attracted to projects by established directors. After having alreayd worked with Coppola and Van Sant, Damon — in the years that immediately followed — appeared in “Saving Private Ryan,” directed by Steven Spielberg, “Dogma,” directed by Kevin Smith, “The Talented Mr. Ripley,” directed by Anthony Minghella, “The Legend of Bagger Vance,” directed by Robert Redford, “Titan A.E.,” directed by Don Bluth, and “The Departed,” directed by Martin Scorsese.

Damon also continued to work with Van Sant while also becoming a regular player for Steven Soderbergh, Paul Greengrass, and George Clooney. He even appeared in two Terry Gilliam movies and two Ridley Scott movies. The man likes working with legends.

As it so happens, he also likes to watch films directed by legends. In 2021, Damon was interviewed by Rotten Tomatoes and the outlet, naturally, asked him to list his five favorite movies. Three of them, it so happens, were made by directors he had worked with before.

Damon, like many of us, isn’t confident in his answer for his favorite movie of all time, as that sort of thing fluctuates depending on a cineaste’s mood. Nevertheless, he’s found that he comfortably relies on a stock answer when his feet are to the fire. It’s also possible he’s comfortable listing it since he worked with its director on “The Rainmaker.” To quote Damon directly:

“I’ve always said ‘The Godfather Part II.’ I think that movie’s pretty near perfect. It’s an impossible thing to answer, your five favorite movies, but I would put that one, just for its direction, its writing, and its acting, its production value. I mean, it’s really amazing. I remember talking to Scorsese on ‘The Departed’ and saying, ‘Hey, Marty: “Godfather 1,” or “Godfather 2?”‘ And he instantly said, ‘Godfather 2.’ And I said, ‘Why’ And he goes, ‘He had more money.'”

Damon also listed Scorsese’s own 1990 crime epic “GoodFellas” as a favorite, saying that he can’t stop watching it once he starts. He is impressed by both its performances and direction, as well as its intense, bloody-minded energy. “It doesn’t feel long,” Damon explained. “It’s just relentless.”

And because the actor worked with Spielberg on “Saving Private Ryan” — he was Private Ryan — Damon seemed compelled to include an early film from the master of modern blockbusters: the ultra-hit “Jaws.” He said he liked the fact that the shark wasn’t visible for most of the movie, even though he knew it was merely because the film’s mechanical shark wasn’t operating properly for much of the shoot. The shark is a creature of the imagination. More so, though, Damon loves Spielberg’s craft, saying:

“It’s like when Hemingway writes, I always go, ‘I know all those words. I just never thought to put them in that order.’ So, there’s nothing that Steven’s doing that’s a trick. He’s got the same equipment everyone else has. He’s just better at telling a visual story.”

Indeed.

It’s almost too easy to list Stanley Kubrick’s 1964 political satire “Dr. Strangelove, or: How I Learned to Stop Worrying and Love the Bomb” as one of your favorites, as it is universally regarded as brilliant, wry, and wicked. Kubrick was very cynical about the state of the world. He witnessed nuclear proliferation with mounting dread and felt that a capricious, buffoonish, or mentally-unstable politician could end the world for whatever ludicrous reason they wanted.

Damon, however, wasn’t so much moved by the satire as he was by the performances of Peter Sellers as the titular Dr. Strangelove, a weak-willed American president, and a visiting British dignitary. (Sellers was actually slated to play a fourth role, but he claimed exhaustion to get out of it.) Damon adored Sellers’ comedic brilliance, explaining:

“It sticks out to me for Peter Sellers, actually. Sellers, I mean, he’s so brilliant in that movie. And I was sitting there wondering, should I go for ‘Being There?’ Should I go for another Sellers movie? I just wanted Sellers on this list, because he was so great. And that’s a movie where he’s as dynamic as he ever was. He played […] three or four different people […] and they’re all just totally different and totally great. That guy was just absolutely brilliant and terribly funny.”

Finally, fifth on Damon’s list was, perhaps surprisingly, Martin Brest’s mainstream road comedy “Midnight Run” from 1988. In the film, Robert De Niro plays a bounty hunter who has to trek across the country handcuffed to his prisoner, a mob accountant played by Charles Grodin. Damon says he watched the film incessantly in college, so it became personal for him. It’s probably no coincidence that it stars De Niro … who directed Damon in “The Good Shepherd.”

Interestingly, Damon also cited Quentin Tarantino’s “Pulp Fiction” as being one of his favorite films when interviewed by Letterboxd in 2023. “I was at [Grauman’s] Chinese Theatre opening night of ‘Pulp Fiction’ in 1994. On the Friday night, Ben [Affleck] and I were there together. It was like being at a rock and roll concert, you know what I mean? Like that got us so fired up about what movies can do. That was definitely a highlight in my moviegoing life,” he explained.

Surprisingly, Damon has yet to headline a Tarantino film.