He has a knack for needing to be rescued, doesn't he? Since the late 1990s, Matt Damon has enjoyed rarified stardom in Hollywood as one of the industry's most bankable leading men. Versatile as both a dramatic performer and an action hero, Damon's movies span a million and one different genres. But which ones should actually be considered his greatest of all time?
Born in Cambridge, Massachusetts, Damon discovered acting in high school. That's also where he met his best friend Ben Affleck, who would later become a major Hollywood player in his own right. While at Harvard University, Damon and Affleck drafted the first versions of what would become their 1997 classic Good Will Hunting - a movie that would get them into the rarefied spaces of Hollywood.
At age 18, Damon made his feature film debut with a one-line role in the 1988 movie Mystic Pizza (which famously stars a young Julia Roberts). In 1992, Damon left Harvard to pursue acting full time despite being just 12 credits shy of graduation. Today, Damon is inescapable as one of the biggest movie stars around the world.
In celebration of his ongoing career, these are the 33 greatest movies featuring one-half of Boston's finest sons.
33. The Brothers Grimm (2005)
Directed by Terry Gilliam, this fanciful adventure co-stars Matt Damon and the late Heath Ledger who play the real-life authors Brothers Grimm. In French-occupied Germany during the 19th century, the Grimms are traveling con men who perform bogus exorcisms. But when they encounter real dark magic and terrifying monsters, the Grimms learn to harness their courage - while collecting inspiration for their legendary fairy tales. Pulpy and silly, The Brothers Grimm is ideal for dark and stormy nights.
32. Air (2023)
A shoe is just a shoe until Michael Jordan steps in it. In this breezy business drama directed by Ben Affleck, the origins of the iconic Air Jordan sneaker are revealed. Matt Damon stars in the role of real-life Nike executive Sonny Vaccaro, who signed Jordan to his first sneaker deal at the start of his meteoric NBA career. As light as its title suggests, Air appeals to anyone drawn in by '80s period movies, the intersection of sports and pop culture, REO Speedwagon needledrops, and the-start-of-something business epics a la The Social Network and BlackBerry. Bonus: Affleck is clearly having fun as a guy who prefers to be barefoot in a posh office.
31. EuroTrip (2004)
Don't tell Scotty! In this raunchy early-aughts comedy, Scott Mechlowicz plays a high school graduate who spends his summer backpacking through Europe to hook up with his hot German pen pal. Matt Damon makes a glorious cameo as the skinhead lead singer of a band who brags in front of Scotty all the ways he's slept with his girlfriend Fiona without him knowing. (The song "Scotty Doesn't Know" by Lustra, which became a legit radio hit, is "performed" by Damon in the movie.) EuroTrip isn't Damon's finest movie, or really his movie at all, but Damon is simply unforgettable as a dirtbag rocker who can stick his tongue out farther than Gene Simmons.
30. Stillwater (2021)
Loosely if also brazenly inspired by the real-life case of Amanda Knox, Stillwater stars Matt Damon as an unemployed roughneck from Oklahoma who fights to protect his daughter's innocence after she's convicted and imprisoned for the murder of her college roommate in France. While mostly conventional and riddled with cliches, Stillwater succeeds through the performances of its leads (particularly Damon) with a timeless story about fighting for the truth when even justice gets it wrong.
29. The Monuments Men (2014)
In this World War II drama that gives The Dirty Dozen an MFA degree, Matt Damon reunites with George Clooney to play Allied soldiers who are given a very special task: retrieving and protecting precious works of art before Nazis destroy them. While critics were mostly cynical towards The Monuments Men, citing its uneven and weepy tone, the movie deserves a proper salute in its riveting and aspirational story about protecting culture from reckless annihilation.
28. Jason Bourne (2016)
Nearly ten years after Matt Damon walked away from the Bourne franchise, he came roaring back as his iconic CIA assassin in the 2016 legacy sequel Jason Bourne. The fifth in the series and the fourth film starring Damon, Jason Bourne - directed by Paul Greengrass - fixes the camera back on the title hero with Bourne on the run from the CIA and fighting off a lethally beautiful Alicia Vikander while trying to uncover the truth about his father. Damon's return to Bourne wasn't quite the electric revival of the series anyone hoped for, but Damon is engaging in this return-to-form installment.
27. We Bought a Zoo (2011)
Admittedly, it's worth watching just for the memes. But Cameron Crowe's sappy 2011 family dramedy We Bought a Zoo is loosely based on Benjamin Mee's 2008 memoir about a widowed father who buys a dilapidated zoo and works hard to renovate it for a grand reopening. Damon leads the movie as Benjamin Mee, with Scarlett Johansson co-starring as the longtime zookeeper who becomes Benjamin's new love interest and surrogate mother to his children. The movie's plain title has become a source of many internet memes in the years since it was released, but We Bought a Zoo has an innocent charm that is worth a day pass.
26. Elysium (2013)
In this action-packed sci-fi about the importance of socialized medicine, Matt Damon plays a criminal on parole who lives on eco-ravaged, overpopulated Earth. When an accident gives Damon's character lethal poisoning with just five days to live, he races against time to get himself aboard the luxurious space station Elysium, where the mega-rich enjoy luxuries including medical treatment that cures anything. As the sophomore effort from director Neill Blomkamp after his game-changing District 9, Elysium was considered a disappointment, but the movie's pointed political commentary with sci-fi thrills is hard to argue against.
25. Interstellar (2014)
Files this one under: "Matt Damon is in this one?!" A little more than halfway through Christopher Nolan's gorgeous sci-fi odyssey from 2014, Matt Damon shows up as a NASA astronaut who is awoken from cryostasis on a frigid planet of ice. While Damon's involvement in the movie was reported a year prior to its release, Damon's absence from most of the marketing materials made his appearance a "surprise" for most audiences to the point his presence was considered distracting by many. Damon doesn't have a lot of screen time either, but that doesn't mean his character doesn't have a crucially important role.
24. Ocean's Thirteen
After Ocean's Twelve bungled the second heist, director Steven Soderbergh got the gang back together for one more round in the most pleasant surprise of 2007, Ocean's Thirteen. Matt Damon returns to his series role as Linus, this time reuniting with Danny Ocean (George Clooney) and the rest to get back at casino owner Willy Bank (Al Pacino). Yet another slick and entertaining heist movie in the vein of the first Ocean's Eleven, Ocean's Thirteen delights in just how much its A-plus cast fire on their perfected cylinders.
23. The Bourne Supremacy (2004)
After The Bourne Identity cemented Matt Damon as a worthy action lead, The Bourne Supremacy kept up the momentum of his rising Hollywood star as a muscular sequel. The Bourne Supremacy once again follows Damon's amnesiac CIA assassin who tries to learn more about his mysterious past. The Bourne Supremacy notably marked the first collaboration between Damon and director Paul Greengrass (who replaced Doug Liman from the first Bourne), with the two working again on more Bourne movies as well as on 2010's Green Zone.
22. Invictus (2009)
In a world divided, great unification can be found in sports. In this stately period drama from director Clint Eastwood, Matt Damon plays real-life South African rugby star Francois Pienaar, who is personally approached by South African President Nelson Mandela (Morgan Freeman) to win the 1995 Rugby World Cup for the good of post-Apartheid South Africa. While Invictus isn't terribly ambitious as anything more than an inspirational sports drama, the emotions it does stir within is nothing to underestimate.
21. The Informant! (2009)
Its predominant ironic tone is off-putting to many, including critics who gave it mixed reviews. But The Informant! has enough entertainment value to make its story about entrepreneurial conspiracy and embezzlement feel like a gas. Based on the 2000 nonfiction book by Kurt Eichenwald, The Informant! stars Matt Damon as Archer Daniels Midland executive Mark Whitacre, who blew the whistle on the company's price-fixing of lysine in the 1990s. The FBI recruits Whitacre as a spy to work as an informant against his own company, but Whitacre seems all too thrilled to be a "secret agent." A more serious approach to Eichenwald's book would have made for a different movie, but it's hard to believe it would be any better than the laugh riot we have instead.
20. The Adjustment Bureau (2011)
The Matrix meets The Manchurian Candidate in this endlessly surprising sci-fi political thriller from director George Nolfi. Based on Philip K. Dick's 1954 short story "Adjustment Team," Matt Damon stars as a disgraced New York congressman who falls in love with an enchanting ballerina (Emily Blunt). But the shadowy forces that pull the world's strings are bizarrely determined to keep them apart. Between a locked-in Damon and its labyrinthine mystery that keeps swerving from expectations, The Adjustment Bureau is something of an underrated highlight in Damon's long career.
19. Contagion (2011)
In this riveting ensemble disaster thriller from director Steven Soderbergh, the modern world collapses at the outbreak of a deadly airborne pandemic. Among its many interlinked narratives, there is everyman Mitch (played by Matt Damon), a suburban family man who tries to protect his teenage daughter as their world changes forever. When Damon was first getting involved with the movie, writer Scott Z. Burns sent him a copy of the script with a note that read: "Read this and go wash your hands." While inspired by the 2002 SARS outbreak and the 2009 flu pandemic, the movie found renewed morbid interest amid the COVID-19 pandemic of 2020.
18. Courage Under Fire (1996)
At the start of Matt Damon's career, the actor had a supporting role in the Meg Ryan/Denzel Washington blockbuster Courage Under Fire. Directed by Edward Zwick, this powerhouse Gulf War-set drama sees Washington playing a Lieutenant Colonel who investigates the case of an army captain (Ryan) and her heroic rescue of a helicopter crew that may posthumously earn her the Medal of Honor, only to realize things are more complicated than they seem. Damon's role as a drug-addicted soldier gave him his first true exposure as a budding star; critic Rita Kempley, in her review for The Washington Post, called Damon's performance in the movie "impressive" as a "psychologically emasculated" member of Meg Ryan's men.
17. Behind the Candelabra (2013)
Obsession and possession are mixed into a deadly cocktail in Behind the Candelabra, Steven Soderbergh's riveting adaptation of the 1988 memoir by Scott Thorson. Based on true events, Matt Damon plays Thorson, a young man who is taken in by the famous pianist Liberace (Michael Douglas) as his personal "companion" and whose luxurious lifestyle is now paid for by Liberace. Over time, Liberace's vise grip over Scott becomes controlling to the point of obsessiveness, with Scott quietly fighting to claim some of his own independence. Acclaimed by critics, the prestige of Behind the Candelabra marked a turning point for television productions and by HBO specifically to truly rival the cinematic offerings by movie studios.
16. Titan A.E. (2000)
In this sci-fi epic from animation auteur Don Bluth, Titan A.E. blasts audiences to the outer reaches of space in its story about humans who wander a galaxy full of hostile aliens after Earth is completely destroyed. Matt Damon voices lead protagonist Cale Tucker, a young man whose possession of an important and rare ring holds the key to humanity's next permanent home. This underrated sci-fi gem memorably combined hand-drawn animation with then cutting-edge CGI, making the picture a symbolic link between different eras of cinematic animation. Although it bombed in theaters, Titan A.E. has grown into a cult classic, boasting a universe of immense potential far bigger than its expansive frames can contain.
15. Rounders (1998)
Arriving just a little too early for the cultural poker boom to give it clout during its 1998 release, Rounders is a high-stakes drama that goes all-in. Matt Damon co-stars with Edward Norton, the two playing friends who must win high-stakes poker games in order to pay off a huge debt to a Russian gangster. While Rounders isn't a top-to-bottom Royal Flush, reliably engaging performances from Norton and Damon make it very entertaining. By the time poker became a phenomenon circa 2003 - thanks in large part to cable TV airings of the World Series of Poker and the growth of online poker - players began citing Rounders as a must-watch movie.
14. Syriana (2005)
Stephen Gaghan's Syriana, based on Robert Baer's 2003 memoir See No Evil, is mostly a vehicle for George Clooney to shine. But Matt Damon enjoys second billing prominence in the supporting role of Bryan Woodman, an American energy analyst in Geneva whose son dies at a private party hosted by a Persian oil prince; the death, while traumatic, leads to a critical opportunity by Woodman and for the United States at large. Damon is just one piece of a vast puzzle assembled by director Gaghan in his searing epic portrait of global power.
13. Oppenheimer (2023)
Past all those "Barbenheimer" memes that dominated the summer of 2023, Christopher Nolan's Oppenheimer maintains its grand designs as an American epic that interrogates the true costs of scientific achievement and peace. While Cillian Murphy takes center stage in the titular lead, as real-life theoretical physicist J. Robert Oppenheimer, Matt Damon plays a major supporting role as General Leslie Groves who oversees the fateful Manhattan Project. Oppenheimer isn't necessarily Damon's movie to own, but its outsized scope and majesty make it practically mandatory viewing with regards to everyone involved with it, Damon included.
12. The Bourne Identity (2002)
Before 2002, Matt Damon enjoyed celebrity status as a Hollywood movie star. But he was not yet a capital-A action hero until The Bourne Identity. Based on Robert Ludlum's 1980 novel and directed by Doug Liman, The Bourne Identity follows Damon as Jason Bourne, an amnesiac who slowly figures out his identity as a top assassin for the CIA. More than just a hit summer tentpole, The Bourne Identity further launched Matt Damon to stardom and gave the action movie genre a new look and aesthetic, one that shied away from the buff masculinity of Stallone and Schwrazenegger in favor of something more focused, more composed, and more lethal.
11. The Bourne Ultimatum (2007)
Rising above expectations as yet another action threequel, The Bourne Ultimatum delivers the goods with Damon in his finest and sharpest form as an action star yet. The third Bourne movie, directed by Paul Greengrass, again follows Matt Damon as Jason Bourne, who is still trying to piece together all his memories when a newspaper reporter puts him on the trail of a superpowered version of the military operation that created him. Hailed as one of the finest action movies of the new millennium, The Bourne Ultimatum gave Damon a fine send-off until he returned for 2016's Jason Bourne.
10. Ford v. Ferrari (2019)
Le Mans, 1963. Italian automaker Ferrari is dominant in the prestigious 24 Hours of Le Mans, but the American Ford Motor Company - in an effort to boost lagging sales - enters the race to put some respect on their name. That's when Matt Damon comes in as Caroll Shelby, an ex-racer and automotive designer who compels British driver Ken Miles (Christian Bale) to work with him on the creation of a car and a team that can outrun both Ferrari and the world where it counts. A handsome motorsports epic about the dangers of chasing artistic perfection under the pressures of capitalism, James Mangold's Ford v Ferrari is a modern classic that dares to push the needle.
9. Dogma (1999)
Talk about holy hell. In Kevin Smith's sacrilegious satire Dogma, Matt Damon and Ben Affleck co-star as exiled angels from heaven who stumble upon a "loophole" on Earth that could bring them back to the pearly gates. Except should they do so, they prove God wrong and thus "unmake the world" (so says an engrossing Alan Rickman as the Metatron). A lonely abortion clinic employee, played by Linda Fiorentino, is tasked by heaven to stop Damon and Affleck's avenging angels before it's too late. Arguably the best movie ever from writer/director Kevin Smith yet woefully underrated in both Damon and Affleck's filmographies, Dogma is an irreverent religious epic that puts the "God" in "Oh my God, dude!"
8. The Last Duel (2021)
A medieval epic for the #MeToo era, The Last Duel details the very last recorded trial by combat in 12th century France. (The story is based on Eric Jager's nonfiction historical book from 2004.) Matt Damon plays Jean de Carrouges, a knight who challenges his former friend and squire Jacques le Gris (Adam Driver) to judicial duel after his wife Marguerite (Jodie Comer) accuses Jacques of sexual assault. With impeccable direction by legendary Ridley Scott, The Last Duel asserts that there is still a place in Hollywood for R-rated epics.
7. The Departed (2006)
It's always a treat to hear Matt Damon in his native Boston accent. In this acclaimed gangster epic from Martin Scorsese (and a remake of the Hong Kong classic Infernal Affairs), Matt Damon leads as a man raised by an Irish mob boss (Jack Nicholson) to work as a spy in Massachusetts state law enforcement. His fate is parallel to that of an undercover state trooper (Leonardo DiCaprio) who is tasked with infiltrating the mob. The Departed is a 21st century classic loaded with intrigue and themes of identity conflicting with obligation, and it's just unsurprising that a director like Scorsese gets an A-plus performance out of his cast including Damon.
6. The Talented Mr. Ripley (1999)
Shortly after his star-making turn in Good Will Hunting and Saving Private Ryan, Matt Damon mesmerized audiences in his performance as the calculating, conniving antihero Tom Ripley in Anthony Minghella's 1999 classic The Talented Mr. Ripley. Damon plays the title character Ripley, a troubled young man who craves a life of luxury; he's approached by the father of Dickie Greenleaf (Jude Law) to bring Dickie and his beautiful girlfriend (Gwyneth Paltrow) back home from Italy. When Tom's efforts initially fail, Ripley goes to terrifying lengths to make Dickie's life his own. Compared favorably to the 2023 black comedy Saltburn, The Talented Mr. Ripley certainly showed off the talents of Damon, who was now more than a handsome face.
5. Saving Private Ryan (1998)
Saving Private Ryan is remembered for a lot of things: The masterful directing by Steven Spielberg, the nightmarish experiences of war that dispel Hollywood-imagined heroism, and Tom Hanks as a surprisingly unsympathetic U.S. captain overcoming his own PTSD. But the movie's PR-oriented mission is to get Private James Francis Ryan back home safely, and that's when audiences meet Matt Damon as the titular character, an otherwise ordinary soldier whose life was deemed to have great meaning by those at the top. With a memorable opening sequence set on the beaches of Normandy, Saving Private Ryan climaxes with a thunderous mission to confront German forces in the torn-up village of Ramelle. A true American epic that is deeply sentimental without weeping nostalgia, Saving Private Ryan is not just a great Matt Damon movie but a great movie period.
4. The Martian (2015)
"Bring him home." Thus was the mission statement of The Martian, the 2015 late summer blockbuster based on author Andy Weir's self-published best-seller from 2011. Damon leads as Dr. Mark Watney, an astronaut and botanist who is stranded on Mars; Dr. Watney cleverly uses his precious few resources (including, gross, the human waste of his departed colleagues) to survive on the red planet until he can be returned home in one piece. Weir's novel was celebrated for its intricate detail, humor, and scientific accuracy. Ridley's cinematic adaptation appropriately follows suit, with Damon also soaking the spotlight as a man to be rescued but learns how to keep his distress at bay.
3. True Grit (2010)
Only the Coen Brothers can outdo John Wayne. In 2010, the auteur directors unleashed the neo-Western classic True Grit, where Jeff Bridges stars as a boozy lawman who is hired by a teenage farm girl (Hailee Steinfeld) to chase after the outlaw who killed her family. Along the way, they meet a similarly determined Texas Ranger named LaBoeuf, played by Matt Damon, who is after the same man. Impressively a finer movie than the '69 original, True Grit is a mighty fine picture that brings some dirt back under the fingernails of an IP and remake-obsessed Hollywood.
2. Ocean's Eleven (2001)
Being cooler than the Rat Pack is perhaps the greatest heist of the century. Over 40 years after the original Ocean's Eleven hit theaters, Steven Soderbergh teamed up with A-listers George Clooney, Matt Damon, Brad Pitt, and Julia Roberts for a vibrant remake set in 21st century Las Vegas, in which Danny Ocean (Clooney) assembles a killer team to steal a whopping $160 million from a slimy casino owner (Andy Garcia). Soderbergh's version of Ocean's Eleven is clever and charismatic, wielding the full might of its many enviable stars. Damon somehow isn't even the shiniest part of the ensemble - hard to be, when you've got Clooney, Pitt, and Roberts on the call sheet too - but Ocean's Eleven is impossibly great by any measure.
1. Good Will Hunting (1997)
Never forget the immortal words: "I gotta go see about a girl." Gus Van Sant's tender drama from 1997 was the calling card for both Ben Affleck and Matt Damon, lifelong friends who came up in Hollywood together through their Oscar-nominated screenplay. Originally conceived by Damon as an action-thriller, the movie evolved into a grounded drama about a young man with superior intelligence who is pushed by different forces into seizing on his gifts or living life the way he deems fit. Damon stars as Will Hunting, who shines in the picture as a brilliant and sharp-witted young man who falls for a beautiful woman (Minnie Driver) while figuring out his path in life. A celebrated picture that also contains one of Robin Williams' most empathetic performances, Good Will Hunting stands the test of time.
