July 3, 2026
As we begin this journey through the career of Matt Damon, in advance of his starring role in Christopher Nolan’s The Odyssey in two weeks, I need you to take a deep breath with me. Most of us became aware of Damon thanks to his starring role in Good Will Hunting. He was nominated for Best Actor and won an Oscar for co-writing the screenplay with his good buddy Ben Affleck. Their Oscar acceptance speech remains one of the best of all-time – you can relive it here if you want to put a smile on your face. Why the deep breath? Next year marks the 30th anniversary of that film. I know, it’s hard to believe, but look it up – it’s actually been almost 30 years. 1997 was an incredible year in the history of movies and I’m planning a retrospective look at those films next year.
Now, as I planned my blog topics for this year, Damon’s career seemed like a no-brainer, but as I made my way through his filmography the last few months, I was wrestling with how to cover his most impressive performances. He’s been in dozens of movies, some in the lead role, others in a supporting performance and many times in a cameo or voice acting role. Trying to rank his top ten movies seemed impossible. For instance, he plays the titular role in Saving Private Ryan, a five-star masterpiece, but it’s a supporting part. He shows up late in the runtime of Interstellar, another masterpiece (at least to this viewer), but again, it’s a minor role. So, ranking the top ten movies he’s appeared in might not showcase enough of his work. And if I just looked at his best performances, I might be ignoring some of those brilliant pictures where he barely appeared. So, no generic top ten list this time. Instead, we’re going to tackle this a little differently.
Early Promise
Damon grew up in the outskirts of Boston (if you didn’t know that, where have you been?) and began acting in the late 1980s. He had several minor roles before his breakout performance in School Ties in 1992. We’ll get to that one in a moment as it sets the tone for Damon’s unique ability to play a shit heel throughout his career. But first I want to mention three roles in the late 1990s that demonstrated he had true acting chops.
In 1996, Damon lost 40 pounds to play a soldier suffering from post-traumatic stress disorder in Courage Under Fire. The film is best known as a showcase for Denzel Washington as a military officer investigating an incident during the Gulf War. He must determine if a helicopter pilot, played by Meg Ryan in an against-type role, deserves a medal of honor after she is killed while trying to rescue her fellow soldiers. Damon portrays one of those men who were on site during the incident who was deeply impacted by the events. He developed a drug problem, which led to his weight loss, and when you see Damon’s performance, you can see just how much he committed to this role.
The next year, he was hand-picked by Francis Ford Coppola to star in The Rainmaker, an adaptation of John Grisham’s bestselling novel. He’s very good in the role, despite some shaky accent work, and what impresses me about this movie is that Coppola saw something in him to play Rudy Baylor. A few weeks later, Good Will Hunting premiered to great acclaim and Damon would become a household name. And six months later, he appeared in the climactic third act of Saving Private Ryan. Contrary to popular belief, director Steven Spielberg did not cast him based on his performance in Good Will Hunting. No, Spielberg was impressed with his work in Courage Under Fire and when he met him in person, thanks to an introduction from Robin Williams on the set of Good Will Hunting. There’s a reason legendary directors are legends – they can spot talent a mile away.
Unlikely Action Star
Given their close friendship, Damon and Affleck’s careers have been compared many times over the years. Affleck’s has been a wild rollercoaster with several ups (winning the Oscar for Argo) and downs (looking at you, Gigli), whereas Damon’s has been very steady. A few minor bumps here and there, but nothing disastrous that would warrant the need for a comeback, which Affleck has done several times. Now, coming out of Good Will Hunting, Affleck seemed most likely to be the action star. He had that tough-guy look and attitude, and you can see that with his appearances in films like Armageddon and Pearl Harbor. Hell, he would eventually play Jack Ryan and Batman. So, it was a bit of a surprise when Damon was announced as the lead in the big-screen adaptation of Robert Ludlum’s popular novel, The Bourne Identity.
The first film in what would eventually be a five movie franchise was released in 2002 and was a huge hit. Damon played an assassin for the CIA who wakes up with amnesia after being rescued at sea, and must figure out who he was before the incident. He knows nothing about his past, but when confronted with danger, his training techniques kick in and he beats the shit out of anyone who gets in his way. Damon is terrific in the role and it’s funny watching this movie so many years later because he looks so young, and kind of scrawny for a hitman. He would go on to play Bourne three more times, declining to return for the fourth installment, leading to Jeremy Renner to step in. Overall, this is a very good action franchise and it’s nice that Damon has this on his resume, and that he was fortunate to do these films in his 30s before he aged out of this type of role.
Just Part of the Gang
One of the things I love about Damon’s career is that he seems to be willing to take on any kind of role, regardless of how big it is. In 2001, he appeared as one of the Ocean’s Eleven gang in Steven Soderbergh’s remake of the 1960s Rat Pack movie. Led by George Clooney, Brad Pitt, and Julia Roberts, the film was a massive hit and even though Damon is farther down on the call sheet, he plays a pivotal role in helping the gang pull off their heist. He played Linus Caldwell, a novice thief who just wants a role in the big con, but has to learn the ropes from Danny (Clooney) and Rusty (Pitt). He gets a few moments to shine, particularly when he swipes the casino security codes from tough guy owner Terry Benedict (Andy Garcia), and chastises Danny after the batteries for their remote controlled detonator fail them. Damon would return for two more Ocean’s movies, which are both pretty good, but not as revered as the first one. He gets more of the spotlight in the third installment when he wears a prosthetic nose in disguise while trying to seduce a casino executive, played by Ellen Barkin, in a very funny sequence. If it’s been awhile since you watched an Ocean’s movie, what are you waiting for?
Making the Rounds
Ocean’s Eleven was the first of nine collaborations with Soderbergh over the years, some of which were minor cameos, and one in particular that I think is brilliant. We’ll get to that one in a minute. It goes to show you that Damon will answer the phone whenever he gets the call, especially if it’s with a director he respects or wants the chance to work with. He reminds me a lot of Leonardo DiCaprio in that way, although Damon is more prolific than Leo in taking on roles. In fact, a funny anecdote that came out of the promotion for Oppenheimer was Damon recounting the story of when he got the call from Christopher Nolan to play the role of Leslie Groves. He had made an agreement with his wife to take a break from acting, but there was one exception – if Nolan called about a job, he had to take it. We all know what happened, because he was fantastic in Oppenheimer, which convinced Nolan to cast him as the lead in The Odyssey. Sometimes things just have a way of working out.
Over the years, the list of directors Damon has worked with is a who’s who of big names. Clint Eastwood, Martin Scorsese, Joel and Ethan Coen, Alexander Payne, Robert De Niro, Ridley Scott, George Clooney, Cameron Crowe, and Gus van Sant, among others. Damon is willing to put his trust in the hands of the director and take a chance, when needed. Of course, not all of these risks work out. His work with Terry Gilliam (The Brothers Grimm and a minor part in The Zero Theorem) do not need to be added to your watchlist. And I can’t imagine what convinced him to star in The Great Wall, a mediocre (at best) action film about samurai warriors fighting off monsters atop one of the seven wonders of the world.
Damon’s two films with Clint Eastwood are kind of interesting. He played a South African rugby player in 2009’s Invictus, alongside Morgan Freeman as Nelson Mandela. Invictus is decent and Damon is pretty good, despite some subpar accent work. He has told the story about how he had some takes where he wanted to do the scene again because his accent was bad, but Eastwood (notorious for quick shooting schedules and only doing a few takes) would say, “Nope, we’re good. Moving on. No need to waste everyone’s time.” Who are we to judge? The performance earned Damon an Oscar nomination for Best Supporting Actor and would lead to Eastwood casting him in his next film, 2010’s Hereafter. He played a man with psychic powers in a story focused on multiple people and their connection to the afterlife. It’s an interesting story and a nice departure for Eastwood and Damon, but not exactly great cinema.
Taking Risks
I love it when actors take risks with the roles they choose. It shows they are willing to go out on a limb, stretch their abilities, sometimes at the risk of embarrassing themselves. One of the biggest chances Damon took was in 2013 when he co-starred with Michael Douglas in Behind the Candelabra for director Steven Soderbergh. Douglas played Liberace and Damon played his longtime companion, Scott Thorson, whose book was the basis for the film adaptation. The movie took forever to make as many in Hollywood felt the story wouldn’t resonate with audiences. Leave it to HBO to step up and commit to the project. The film was a critical and awards success, and it’s primarily due to the performances of the two leads and the creative force of Soderbergh, one of my all-time favorite directors.
On the contrary, another one of Damon’s risk-taking choices was viewed as a disaster, but I think the failure of Alexander Payne’s Downsizing was primarily a marketing problem. The film was advertised as a goofy comedy about a couple (Damon and Kristin Wiig) who choose to undergo a radical new procedure to help the environmental crisis, by shrinking themselves down to a small size. Unfortunately, the movie is also about the existential dread of feeling alone when Wiig’s character changes her mind. The second half of the film (which is admittedly too long) is not very funny, which I think alienated audiences. I rewatched Downsizing recently and it has some good things going for it, particularly Damon’s terrific performance, but it is still pretty uneven.
Damon is also not above taking a bit role if he thinks it will be a fun experience. He’s appeared in several Marvel and Kevin Smith movies, sometimes in a blink and you’ll miss it appearance. A few of these were last-minute deals where he happened to be available to jump on a plane at a moment’s notice. The most famous of these was his hysterical appearance in EuroTrip, the teen comedy released in 2004. He was filming The Brothers Grimm in Prague and agreed to show up on the set of EuroTrip, which was shooting nearby, to play a punk rock singer. His character recently began dating the girlfriend of the movie’s main character, Scotty, and was performing with his band at a party. His performance of Scotty Doesn’t Know (a very catchy tune) became an iconic performance in his long career.
Lastly, Damon is not done taking risks with his acting choices. He is reportedly signing on to star in the next film from Daniel Kwan and Daniel Scheinert, in their follow up to the Oscar-winning Everything Everywhere All at Once. They are known for making wild decisions with their storytelling and if you saw their last film (which I thought was just average), you know what I mean. Not much is known about their new picture, but I’m guessing it will be a crazy story and with Damon involved, I’ll be seeing it open weekend.
Playing the Shit Heel
Another aspect of taking on risks in your roles as an actor is being willing to play a despicable person. A lot of times, we think “Oh, Matt Damon – he’s so charming, I like him!” but there are plenty of roles where he plays a truly evil person. For instance, if you first saw him in 1992’s School Ties as an antisemitic sleazebag football player trying to besmirch the new student played by Brendan Fraser, your natural reaction was probably, “What an asshole.” Looking back on it now, you can say, “What a terrific actor.”
Fortunately for admirers of Damon, he has come back to playing the asshole with great effect a few other times in his career. He co-starred in Martin Scorsese’s Best Picture winner The Departed in 2006, playing a corrupt police detective. He’s on the take from mobster Frank Costello (a character inspired by Whitey Bulger and played by Jack Nicholson), and as the walls close in on him toward the end of the film, we see just what a disgraceful coward he really is. I am a big fan of The Departed and think that Leonardo DiCaprio owns that movie with the range he displays in his performance. It’s a shame that he only shares a few scenes with Damon as they are terrific on screen together. Imagine if we could get another movie co-starring these two big stars. Now that would be fun.
Eight years later, Christopher Nolan took us on an interplanetary journey with Matthew McConaughey and Anne Hathaway on a mission to save the planet. Interstellar is a magnificent feat of filmmaking from Nolan and once again, he mastered the casting decisions. And I say that not just because he gave Timothée Chalamet one of his first roles. About two-thirds of the way through the film, the crew lands on a planet to check on a brave astronaut who traveled there many months before on a scouting expedition. When he emerges from his protective sleep, we see our good friend Matt Damon appear. Oh, isn’t that nice! I love it when he shows up in a movie. We soon learn that he plans to sabotage the mission to get back to Earth and abandon the cause for which he originally volunteered. Just a true shitbag that gets his comeuppance a few minutes later when trying to board the main ship, in a fitting conclusion to his story arc.
One other role worth mentioning is one of my favorite movies of 2021, but was missed by a lot of people because it was released in the midst of the pandemic. Damon and Affleck co-wrote a draft of The Last Duel, a medieval story about a woman who is raped by her husband’s rival. The story is told from the perspective of the three main characters in a Rashomon-style of storytelling. As the script was coming together, Damon and Affleck realized they needed a better perspective for the portion of the film told through the eyes of the woman. They brought in writer-director Nicole Holofcener and the three of them delivered the final script to director Ridley Scott, who directed the shit out of this movie. It features excellent action sequences and terrific performances from the three leads – Damon, as the shitty husband who doesn’t believe his wife, played by Jodie Comer, and Adam Driver as the man who rapes her. Throw in a comic supporting performance from Ben Affleck, and The Last Duel has everything.
The Best of the Best
I couldn’t bring myself to do a proper top ten list, but I have to showcase four essential picks from Damon’s filmography. Are these my four favorites? Maybe. Either way, they are definitely really high on any list.
We have to start with Good Will Hunting, in which he played the title character, the tortured genius who wants to prove to everyone how smart he is, but can’t get out of his own way to do anything with his intellectual abilities. He is pushed to do something with his life by his lifelong friend Chucky (Affleck), his court-appointed therapist (Robin Williams, in a brilliant Oscar-winning performance) and his girlfriend (Minnie Driver.) Just an absolutely beautiful film with humor, heart, and some iconic lines. While I’m here, I have to mention Rounders, the poker buddy drama Damon made right after Good Will Hunting. He co-stars with Edward Norton in one of my favorite movies of the 1990s.
If we are talking about the most impressive performance Damon has ever given, I might have to go with The Talented Mr. Ripley, released just two years after Good Will Hunting. He gets completely lost in the role of Tom Ripley, the scheming young man who weasels his way into the life of Dickie (Jude Law) and his girlfriend Marge (Gwenyth Paltrow) on the beautiful Italian coast. The way Damon plays Ripley as everything from a nebbish nerd to a homicidal maniac is truly astonishing. The film (directed by Anthony Minghella) is gorgeously shot, has a terrific soundtrack, and includes strong supporting performances from Philip Seymour Hoffman (one of the best character entrances in movie history) and Cate Blanchett. A true masterpiece film. Also, if you haven’t seen the limited series reimagining of this character, Ripley (with Andrew Scott in the lead role) is on Netflix and is as impressive as Minghella’s version.
Damon showcased his comedic chops in The Informant!, which is probably the least seen of these four picks. Director Steven Soderbergh recruited him to play Mark Whitacre, a whistleblower who helped expose a price-fixing scheme conducted by the manufacturer of a food additive. Sounds like a corporate-espionage thriller, right? Nope, this is a dark comedy with Whitacre driving everyone around him crazy, especially the FBI agents, who want him to inform on his employer. But Mark keeps changing his mind about what he wants to do, and more importantly, changing the facts about what is really going on. Damon is so impressive because he has to play this role in a very serious manner, despite the hysterical actions he is actually taking. A true underrated gem if you’ve never seen it, but be sure to listen carefully so you can hear all of Mark’s fabrications throughout the story.
No list of the greatest Matt Damon movies would be complete without 2015’s The Martian, the role that probably should have won him Best Actor at the Oscars that year. He lost to DiCaprio for The Revenant, in an award that was really a lifetime achievement Oscar, making up for the several times he should have already won. Damon plays Mark Watney, the astronaut stranded on Mars after the crew leaves the planet, thinking he perished in an accident. He is forced to “science the shit” out of his situation and figure out how to get home. The Martian is an A+ Hollywood movie and it only rises to that elite level because of Damon’s performance. If you don’t feel the same fear he does, empathize with his pain and suffering and (most importantly) laugh along with his jokes, The Martian is not nearly as effective as it turned out to be. Think about how many scenes where he is the only one on screen, talking to a camera. Just elite acting from one of our great movie stars in yet another terrific Ridley Scott film that is essential for any Damon fan.
Making the Transition
As Damon has made his way into his 50s (I won’t call him old, because he’s only two years older than me), he has started taking on more of what I would call “Dad” roles. He’s not like Tom Cruise where he’s going to run all over the world and chase down the bad guys. Although, he could make another Bourne movie – who knows?
In 2019, he played opposite Christian Bale in the magnificent racing film Ford v. Ferrari. He played the veteran driver who had to retire and finds interest in a different side of the sport – building the perfect car instead of driving it. He taps Bale’s character for that job, but he still brings the passion to the role he’s been chosen for, and Damon is very good as the “veteran” of the team.
That performance reminded me of the role he played in the development of 2016’s Manchester by the Sea. Damon served as a producer on the film, which was written by his good friend Kenneth Lonergan. The two previously collaborated on the terrific 2011 film Margaret. Damon was originally going to play the lead character of the tortured husband in Manchester, but as the production was moving along, he and Lonergan agreed that he was too old to play the part. So, they offered it to Casey Affleck, who would go on to win the Oscar for Best Actor. The film was nominated for six Oscars, with Lonergan also winning for Best Screenplay, but ultimately lost Best Picture (to Moonlight) and Best Director (to Damien Chazelle for La La Land.). You might remember that ceremony. A funny anecdote about that night is that host Jimmy Kimmel (who has a running bit that he and Damon hate each other) said that he considered pretending that Manchester by the Sea won Best Picture, because Damon would have thought he won an Oscar as one of the film’s producers. Good thing he didn’t play that joke, since Warren Beatty and Faye Dunaway created the chaos on their own.
Damon has continued his producing role in recent years, partnering with Ben Affleck to form Artists Equity, their production company. They are focused on putting the artists first, and ensuring they get adequately compensated for their work, regardless of their job on the film or their level of fame. In working with Netflix for their recent collaboration The RIP (a pretty good crime-drama in which they also both starred), they created a unique compensation structure in which all members of the crew could share in bonuses if the movie achieved certain streaming metrics.
Affleck continues to act, but is more focused on filmmaking lately, as we saw with 2023’s Air, the origin story of Nike’s creation of the Air Jordan sneaker for Michael Jordan. Damon stars as Sonny Vaccaro, the basketball scout who convinces Nike owner Phil Knight (played by Affleck) to risk it all to create the shoe for Jordan and sign him to a lucrative contract. This is a classic example of Damon taking the “older guy” role, much like we saw with Paul Newman in the latter days of his career. Air is an excellent film that offers several moments of nostalgia for those of us who grew up in the 1980s.
The two good friends planned to work together again for Affleck’s next directorial effort, Animals, the action-thriller currently in production. The plan was for Damon to star in the lead role until he got the call from Nolan to star in The Odyssey. I love to imagine that phone call to Affleck. “Hey Ben, I know we’ve been buddies forever and I made a commitment for your next film. But this is the role of Odysseus for Christopher Fucking Nolan!” I’m sure Affleck wished him good luck, right before he decided to play the role in the film himself, which we might see later this year.
And that brings us to Damon’s latest work with Nolan, first as the veteran general Leslie Groves, who recruits Robert Oppenheimer (Cillian Murphy) to lead the Manhattan Project in 2023’s Best Picture winner Oppenheimer. Damon is superb in the role and was definitely overshadowed by Murphy and Robert Downey, Jr., both of whom won Oscars for their performances. Damon plays the general with gravitas, but also moments of humor. Do you remember the scene where Oppenheimer tells him that the chance of the bomb test blowing up the planet was technically greater than zero? The look on Damon’s face? The rare funny moment in a tension-filled drama.
Now we get to see what Damon does with one of the oldest characters in history. He plays the king who must find his way back to his family following the Trojan War. I am far from an expert on The Odyssey (I may have read it in school – I don’t remember), but I was ecstatic with this casting. It gives him another chance to shine as the lead character, among an impressive ensemble cast that includes Anne Hathaway, Tom Holland, Robert Pattinson, Charlize Theron, Zendaya, and Lupita Nyong’o, among many others. As impressive as this cast is, I am most curious about Damon and what he brings to the film. Could Nolan deliver him a Best Actor Oscar like he did for Murphy three years ago? Well, Tom Cruise, Ryan Gosling, and other talented actors will likely have something to say about that. But I’m getting ahead of myself.
We know that Nolan is the master technician when it comes to filmmaking and The Odyssey is the movie event of the year. It’s a big-budget epic that will be in theaters on July 17th and demands to be seen on the big screen. My son and I are headed to Boston to see it on 70MM at the Coolidge Corner theater, a beautiful spot where we saw Kill Bill: The Whole Bloody Affair last year. Tickets are now on sale at your local theater – be sure to grab yours, so you can see the next Damon performance in what will likely be another Nolan masterpiece.
That’s all for this week. I hope you enjoyed my look at the career of one of my favorite actors. If you want to watch any of my recommendations, you can go to JustWatch.com to find where to stream or rent them. I’ll be back at the end of the month for a look at some new releases, including The Odyssey, the new Spider-Man movie, and The Invite, a comedy that is getting incredible buzz following early reviews. Thanks for reading and if you would like to be notified about future posts, you can subscribe below.