Matt Damon has been in our lives since he was the bad guy in School Ties in 1992, and by 1997 he was already an Oscar Winner (although not as an actor, but for the Good Will Hunting script). In his career, Damon has done all kinds of movies: comedies (Dogma, the Ocean movies), action (The Bourne franchise), and he’s known for his many cameos (from Thor: Ragnarok to Eurotrip). He has also done incredible dramatic work. Here are his best dramatic performances, ranked:
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8 The Rainmaker (1997)
Paramount Pictures
Rudy Baylor (Damon) is a young, idealistic, and earnest lawyer. The problem is, he’s working for an ambulance chaser, where none of those qualities are valued. Baylor steps into a massive case where more experienced lawyers are representing an evil insurance company. Can he win a case like that?
MOVIEWEB VIDEO OF THE DAY
MOVIEWEB VIDEO OF THE DAY
MOVIEWEB VIDEO OF THE DAY
The Rainmaker was one of Damon’s first leading roles. The movie should’ve been a success as it had Coppola directing it and was a book adaptation of a John Grisham novel. It wasn’t a success, but it showed Damon could keep up with great actors like Danny DeVito, Jon Voight, or Mickey Rourke. Coppola used Damon’s earnestness, inexperience, and wide-eyed looks in one of the first big movies of his career to show a character who was in a similar situation.
7 Margaret (2011)
Fox Searchlight Pictures
Lisa (Anna Paquin) is a 17-year-old who, without it being her fault, becomes involved in an accident where a bus driver runs over a woman. Margaret explores the aftermath of this event and how it affects our lead character, in a movie where emotions are given more importance than actions. It’s one of Anna Paquin’s best performances ever. Damon plays a small part as her math teacher, who grows too fond of his student. Damon always likes to be part of ensembles, even in small roles, if it means working with great actors and directors, as he does here with Lonergan and Paquin. His character is essential to the plot, but not that seen much in the movie (we recommend the director’s cut as Lonergan uses rhythm, and silence incredibly).
6 Rounders (1998)
Miramax Films
Mike McDermott (Damon) is a great poker player who, after losing all his money in one hand, decides to focus on law school. When his friend Worm (Edward Norton) gets out of prison and needs to get money fast to pay some gambling debts, Mike has to go back to his first love and mistress: poker. Rounders is still one of the best poker movies ever; one that appeared right before the poker boom, and showed a world rarely seen in cinema. The dialogue is great, the inside vocabulary becomes understandable, and all the actors are having fun. Damon is the lead, playing a smart guy in between two worlds (poker and law school), anchoring the movie and the rest of the performances in this stacked cast that included Damon, Norton, Famke Janssen, John Turturro, Martin Landau, Gretchen Mol, and John Malkovich in a Russian accent that goes All-In (pun intended). Damon was still unknown back then. The director Dahl, told The Ringer: I went to the video store and rented some movies that he was in. And they sent me a clip from Good Will Hunting. They sent me a scene with Robin Williams. And it was brilliant, I thought. I said, “Great, I’d love to do this movie with this guy nobody has ever heard of.”
5 Courage Under Fire (1996)
Davis Entertainment
Lieutenant Colonel Serling (Denzel Washington) is tasked with determining if a dead helicopter pilot, Captain Karen Emma Walden (Meg Ryan), deserves the Medal of Honor. It would be the first for a woman. He starts interviewing her fellow soldiers about her death, and things don’t add up. Courage Under Fire has great performances by Washington and Ryan (one of her best acting roles in a move very different from what we were used to by her), but it’s Damon who steals the show. He has a small part as Ilario, a medic that was there when Ryan’s character died. Damon lost 40 pounds, and he’s all bones as the heroin-addicted, PTSD-suffering soldier who’s still haunted by what happened that day gives a fragile, ghostly, sad performance.
4 The Departed (2006)
Warner Bros. Pictures Releasing
Boston’s Mafia boss, Frank Costello (Jack Nicholson), has a mole in the police: Colin Sullivan (Damon). They don’t know the police are doing the same, having Billy Costigan (Leonardo DiCaprio) as a mole in Costello’s organization. Chaos and machinations ensue. The Departed was directed by Martin Scorsese (who won his only directing Oscar for this film) and has an incredible cast: Nicholson, Damon, and DiCaprio are the main cast, but they’re supported by the likes of Alec Baldwin, Martin Sheen, Mark Wahlberg, and Vera Farmiga. DiCaprio and Damon play two sides of the same coin. The former has the showiest part, but it’s Damon’s understated performance as the slimy, looks-to-good-to-be-true, crooked Sullivan that creates the perfect balance for the movie. We’ve said it many times: Damon should play more villains as his performances shine when he’s evil, trying to hide by his sweet, good-natured charm.
3 The Martian (2015)
20th Century Studios
During a dust storm, a crew of astronauts has to leave Mars. One of them, botanist Mark Watney (Damon) is thought dead and left behind. But he’s alive, and now must survive on the red planet with only his wit and some materials left behind. The Martian is Damon’s movie through-and-through in this one-man show. He’s alone and has the most screen time, so if he didn’t give a charismatic performance, the movie wouldn’t work at all. Thankfully, Damon is up for the task, as the film shows him having fun while solving problems, and nerding out, while also paying attention to the despair and desperation of someone who is alone and in the worst circumstances ever, in a place where everything can kill you. Damon can do it all in what was one of the best sci-fi movies of the 2010s.
2 The Talented Mr. Ripley (1999)
Paramount PicturesMiramax
Based on Patricia Highsmith’s novel, this movie tells the story of Tom Ripley (Damon), who is sent to Europe to bring back the heir to the rich Greenleaf empire. Once there, he’s more than infatuated with Dickie (Jude Law) and his rich life, so he decides to stay in Italy with him. Things start to go bad, and Ripley starts killing people to keep his newfound lifestyle. He doesn’t want to be with Dickie; he wants to be Dickie and enjoy all life has to offer when you’re young, rich, and handsome.
Damon plays Ripley with less psychopathy than in the book; he’s a conman, both tragic and frightening, as he tries to rationalize every killing. The rest of the cast in The Talented Mr. Ripley is also excellent, getting them all just before they became staple names. There’s Damon and Law, but also Gwyneth Paltrow, Philip Seymour Hoffman, and Cate Blanchett in a movie that made us fall in love with Italy and the Mediterranean life.
1 Good Will Hunting (1997)
Miramax
Will (Damon), is a young, troubled man who works as a janitor at the prestigious Massachusetts Institute of Technology. When he sees a complex math problem on a chalkboard, he solves it, proving he’s a mathematical genius. A teacher there (Stellan Skarsgard), recruits him under the condition that he’ll go to therapy for his anger bursts. His therapist, Sean (Robin Williams in a role that won him an Oscar), helps him cope with his past.
Good Will Huntingis a Cinderella story, not only for the character, but also for Damon and Ben Affleck, who co-wrote the movie, to show their talent as actors. They got many jobs after the film and also won the Academy Award for Best Script. The direction by Gus Van Sant in one of his best movies also helped, though it took them some years to get the project up and running. Damon told Boston Magazine about when things finally started rolling out for the movie, was when was cast in The Rainmaker: I sent Harvey a fax that literally said, “Dear Harvey, I am the Rainmaker.” He called me, and he was like, “What does that mean?” He thought I was getting a lawyer or something. I was like, “No man, I got the Coppola movie; they cast me as the lead.” And Harvey goes, “THE GRISHAM MOVIE? THOSE THINGS MAKE $100 MILLION!” Damon understood the character perfectly (probably because he wrote it and had been with him for years), and that’s why it’s his best dramatic performance ever. And seeing the list of his work in this piece says a lot.
