Entertainment

What Is Matt Damon's Best Movie Role?

Published On 07/28/2016 Published On 07/28/2016
Best Matt Damon movies ranked
Cole Saladino/Thrillist

Matt Damon is hard-working, conscientious, whip-smart, and good-looking -- in other words, he's pretty much perfect. While other movie stars of his caliber seem to resort only to starring in vacuous blockbusters, Damon tends to seek out daring and challenging roles.

This weekend, the 45-year-old will revisit his most iconic character in Jason Bourne. But it's worth asking: is the super-spy really his best role? Let's take a look through Damon's credits and determine that, shall we?

Before we begin, here are a few ground rules: no cameos (sorry, Mystic Pizza, EuroTrip, and The Zero Theorem), no voice work (too bad, Spirit: Stallion of the Cimarron, Titan A.E., or Happy Feet Two), and no TV movies (even one as singular as Behind the Candelabra). Sifting through it all, we have one major takeaway: Damon has appeared in his share of duds over the years, but he has never been bad in a movie. Believe it.

Sony Pictures Entertainment/YouTube

37. Britton Davis (Geronimo: An American Legend, 1993)

Director Walter Hill made some great movies in his heyday (see: The Warriors, 48 Hrs.). Geronimo: An American Legend is not one of them. Yet Damon, who plays the morally conflicted second lieutenant in this Western about the enslavement of the infamous Apache tribe leader, leaves the nearly two-hour movie unscathed. His performance shows the potential of an actor with a lot more to offer under better circumstances.

Columbia Pictures/YouTube

36. James Granger (The Monuments Men, 2014)

World War II soldiers become unlikely art collectors (retrievers, rather) in George Clooney's oversized dullard of a movie. Considering the talent involved (John Goodman, Bill Murray, Cate Blanchett) it's pretty remarkable that this one didn't amount to much. Damon, as always, turns in passable work as a museum curator turned protector of some of the most breathtaking works of art ever created. The movie ultimately proves that perhaps not all art is worth saving, though.

Miramax/YouTube

35. Gerry (Gerry, 2003)

Imagine Waiting for Godot, but without the profundity. That's Gerry, a movie about two dudes named Gerry (Damon and Casey Affleck) who amble through the desert and get lost. That's pretty much all that happens in the first entry of director Gus Van Sant's "death trilogy." It's sluggish, dull, and alienating. Given the semi-improvisational nature of the shoot, Damon does what he can with the material at hand.

Dimension Films/YouTube

34. Wilhelm Grimm (The Brothers Grimm, 2005)

Terry Gilliam's visually and sonically assaultive fantasy jams about 9,000 ideas into two hours. One of its few redeemable concepts is the pairing of Damon and Heath Ledger as brothers Will and Jacob Grimm, cursed con artists who go from town to town staging fake exorcisms. The chemistry between the two is so electric that it almost awakens a tired film.

Paramount Pictures/YouTube

33. Charlie Dillon (School Ties, 1992)

This was the start of Damon and Ben Affleck's creative collaborations in Hollywood, in which Damon played an affluent, anti-Semitic New England prep-school student. Damon drew inspiration from his then-classmates at Harvard, who were thrilled to influence his performance. At 22, he demonstrated his ability to convey the darkness of a character, even if doing so invited the scorn of audiences.

Columbia Pictures/YouTube

32. John Grady Cole (All the Pretty Horses, 2000)

There is brilliant a version of this movie somewhere. At least that's what Damon and director Billy Bob Thornton believe. "You can't cut 35% of the movie and expect it to be the same movie," Damon said to Entertainment Weekly. Regardless, the final cut thrusts him into a disjointed adaptation of Cormac McCarthy's revered novel. At least he does look pretty.

Paramount Pictures/YouTube

31. Rannulph Junuh (The Legend of Bagger Vance, 2000)

Look, the turn of the century was rough for our boy. How was he supposed to know that a Robert Redford-directed period fantasy/drama about a struggling golfer and his mystical caddy wouldn't be good? Even so, Damon assumes the role of Mr. Junuh with confidence. He's ambitious, but not arrogant, charismatic, but not cloying. A few years after Bagger Vance, Damon went on to master this type of role in better films.

20th Century Fox/YouTube

30. Bob Tenor (Stuck on You, 2003)

Does any other movie in Damon's filmography stick out more than Stuck on You? Directed by the Farrelly brothers (Dumb and Dumber), it's the story of conjoined twins (Damon and Greg Kinnear) who move to Hollywood  for one of them to start a career in show business. Whether you find it funny or obnoxious (or both), there's something to admire in Damon's willingness to be goofy and crass. After all, how could you take yourself seriously when you're getting paid to say the line, "We're not Siamese, we're American!"

Focus Features/YouTube

29. Steve Butler (Promised Land, 2012)

No director knows how to both use and misuse Matt Damon quite like longtime collaborator Gus Van Sant. Here Damon plays a likable salesman for a big natural-gas corporation, going door to door in small-town in Pennsylvania. The film reveals itself to be super political, attempting to make grand statements on hot-button issues like the energy crisis, fracking, and lobbyists. The best scenes include Damon and Alice (Rosemarie DeWitt) falling for each other as the world around them grows corrupt.

Tristar Pictures/YouTube

28. Max (Elysium, 2013)

Speaking of politics, this film exemplifies the "message before art" era of Damon's career. He has never been shy about expressing his socioeconomic and political views, and it shows in Neill Blomkamp's dystopic follow-up to District 9: in the year 2154, the film's world, save for the top 1%, resides in utter disarray. Max (Damon) embarks on a dangerous mission to close the gap between the very rich and the very poor. It's an action sci-fi about income inequality that could've worked in the hands of a different director.

Universal Pictures/YouTube

27. Miller (Green Zone, 2010)

Arguably the start of Damon's overtly political chapter, Paul Greengrass' fast-talking, nail-biting thriller revolves around an enlightened U.S. Army officer who goes rogue after discovering government deceit. Damon often selects roles like this one, where he can inhabit the headspace of an upstanding citizen. Green Zone may not consistently entertain, but it does make you contemplate the ethics of the people who haphazardly catapulted us into the Middle East.

20th Century Fox/YouTube

26. SPC Ilario (Courage Under Fire, 1996)

Starring alongside '90s powerhouses Denzel Washington and Meg Ryan, this is the first role for which Damon received critical and public recognition. To play the part of the emaciated Specialist Ilario, he shed 40 pounds through rigorous dieting and workouts. The character is wounded and shell-shocked from the war, with heroin serving as his only refuge. In a supporting role, Damon commands the screen without showboating or chewing up the scenery. The pain of his traumatized soldier is palpable, proving Damon as a force to be reckoned with.

Constellation Entertainment/YouTube

25. Rudy Baylor (The Rainmaker, 1997)

After Courage Under Fire, Francis Ford Coppola offered Damon the role of a young and inexperienced lawyer who fearlessly challenges a fraudulent insurance company in court. All great actors have a lawyer movie, in which they are the arbiters of reason, the incorruptible truth-tellers. Plus, if you're in a John Grisham adaptation, you're guaranteed a chance to deliver a rousing monologue about liberty and justice for all. The Rainmaker was a solid showcase for an emerging Damon.

Paramount Pictures/YouTube

24. Mann (Interstellar, 2014)

Spoiler alert: Matt Damon's appearance as a NASA pilot pioneering a frozen planet in another galaxy is one of the few genuine surprises of Christopher Nolan's bloated blockbuster. However, Damon shows up at the point in which Interstellar takes a left turn in the wrong direction. Still, there are few things more baffling (or comedic) than the wide shot of Mann and Cooper (Matthew McConaughey) fighting on icy terrain, millions of miles away from civilization. From a character standpoint, Damon perfects the act of being a menace. Pity that the end product isn't stronger.

Lionsgate/YouTube

23. Loki (Dogma, 1999)

Dogma is probably the last time Kevin Smith gave a shit behind the camera. In this one, Damon gets to play the role of a lifetime: Loki, the Angel of Death, who's part Norse god, part fallen angel. Smith's casting of Damon proved he understood the actor's comedic chops before anyone else in Hollywood did. The result is one long and uproarious middle finger to the Catholic Church.

20th Century Fox/YouTube

22. Benjamin Mee (We Bought a Zoo, 2011)

It's not a masterpiece, but if you're on a plane and viewing options are limited, you could do worse than We Bought a Zoo. Yes, the idea that anyone -- let alone a father and his family -- would buy a floundering zoo in the hopes of reviving it is stupidly far-fetched. But you know why it kinda works? Because at a certain point you give into Damon and director Cameron Crowe's bold optimism and sentimentality. It's well-done, perfectly calibrated schmaltz.

Warner Bros./YouTube

21. Bryan Woodman (Syriana, 2005)

I've seen Syriana, and I still can't really tell you what the hell is going on or what it's about. It's one of those twisty geopolitical thrillers where no one has all the answers, not even Damon's energy analyst, an elaborate game of connect-the-dots where everyone's dot is on a different sheet of paper. Still, despite the density of the subject matter (the inner workings of the oil industry), Damon is engrossing, capable of inviting the audience into this confusing world.

Warner Bros./YouTube

20. Francois Pienaar (Invictus, 2009)

When it came out, Clint Eastwood's dramatic biopic of revolutionary South African leader Nelson Mandela was deemed a slog, stuffy and overlong without any clear momentum. Okay, fine. That's not entirely untrue. But Damon delivers a low-key good performance as the captain of the national rugby team tasked with uniting a continent in peril by winning the World Cup. He works past the clichés and comes out the other side as downright inspirational, which earned him a well-deserved Oscar nom.

Universal Pictures/YouTube

19. David Norris (The Adjustment Bureau, 2011)

Damon has the rugged charm and charisma of a man who might ditch acting for politics someday. For now, we have George Nolfi's The Adjustment Bureau to live out the fantasy of Damon running for office. The movie is a cocktail of suspense, sci-fi, and romance, as his Norris runs through teleporting doors scattered across New York City. Neil deGrasse Tyson would probably have some questions about the science of it all, but if you give in to the fantasy you'll be won over by Damon's simultaneous playfulness and seriousness. Just look at that fedora! He's wearing it without irony, which is kind of the same way you have to approach this movie.

Warner Bros./YouTube

18. Mitch Emhoff (Contagion, 2011)

Contagion, otherwise known as A Germaphobe's Worst Nightmare, is about a rapidly spreading virus with no cure single-handedly wiping out the world. It's a truly horrifying movie in which Damon plays an everyman whose wife is patient zero of the sickness (Gwyneth Paltrow). He could've played a caricature of a widower, but he dives deeper, into the recesses of a man just trying to save the remaining family he has.

Warner Bros/YouTube

17-15. Linus Caldwell (Ocean's Eleven, 2001; Ocean's Twelve, 2004; Ocean's Thirteen, 2007)

Shout out to Damon for taking the uncool character in a series of very cool movies. Thanks to Steven Soderbergh's precise direction, Damon stands out from the pack as a good-natured, disciplined, and ambitious thief who tries just a little bit too hard. There's a lot of laughing at (not with) Caldwell, and Damon invites the mockery. Of all the characters in the Ocean's universe, Caldwell is the only one who has a true arc: who he is in the first movie is not who he is by the third. What other actor could pull that off within the rigidity of a tentpole series?

Warner Bros/YouTube

14. George Lonegan (Hereafter, 2010)

Some Clint Eastwood melodramas are indefensible (remember J. Edgar?). Hereafter -- despite a negative reception from critics -- is not one of them. How can we take a movie seriously when one of its protagonists is a retired professional psychic? Because Damon is that emotionally bruised psychic, and he turns him into a three-dimensional person. It's a testament to Damon's talents that this movie is worth enduring.

20th Century Fox/YouTube

13. Mark Watney (The Martian, 2015)

While Ridley Scott's space epic isn't filled with wall-to-wall laughs, the only reason The Martian is a joy to watch is because Damon -- with the help of clever screenwriter Drew Goddard (Cabin in the Woods) -- is pure comic relief. He's an astronaut stranded on Mars with little but a sense of humor to keep him afloat. At a certain point, you forget about his quest to return to Earth and just accept the movie as an opportunity for Damon to flex his comedic muscles.

Universal Pictures/YouTube

12. Edward Wilson (The Good Shepherd, 2006)

Although it's nearly three hours long, Robert De Niro's stirring second directorial effort is watchable (enticing, even) because of Damon's layered turn as a CIA agent. Over the course of the movie, Damon is given room to ping-pong across emotions, acting taciturn one moment, then forceful the next, as a devout husband and worried father who's also in possession of some of America's greatest secrets. A decade later, this lesser-watched gem is a secret in and of itself.

Fox Searchlight/YouTube

11. Mr. Aaron (Margaret, 2011)

It may be Anna Paquin's movie, but Damon plays a pivotal part in writer/director Kenneth Lonergan's unnerving tragedy about a teenager who witnesses (perhaps even contributes to) vehicular manslaughter. As Lisa's (Paquin's) professor, Damon is there to console her while her life goes to shit. Until he's not. Until he wants something more. Damon can go dark, and this role proves he can also inhabit the moral gray area of a person.

10-8. Jason Bourne (The Bourne Identity, 2002; The Bourne Supremacy, 2004; The Bourne Ultimatum, 2007)

The defining characteristic of Bourne is that he lacks defining characteristics. How can an actor play an amorphous human being? We inch closer and closer to an answer with each pulse-pounding installment. That watching these movies has yet to feel like a chore must mean Damon is doing something right. Bourne is an enigma, yet we're always invested in the character because Damon manages not to distance himself too much from the audience, always leaving us wanting more.

Dreamworks SKG/YouTube

7. Private Ryan (Saving Private Ryan, 1998)

*Audible gasps* "How dare you place a Steven Spielberg classic behind six other movies!" the comments on this article will surely read. Yes, I know. This is hard to swallow. I promise we'll get through this. See, Private Ryan is the rare example where Damon is good in a movie that is great. If only every scene allowed for the complexity Damon exhibits in the one above, where he manages to make emotional gravity both revealing and uplifting.

Paramount Pictures/YouTube

6. LaBoeuf (True Grit, 2010)

Some movie stars are always themselves -- whether he's a love consultant or a man in black, Will Smith is always Will Smith, for example. Yet when Damon first appears in Joel and Ethan Coen's masterful neo-Western, you forget who you're looking at. He sinks into the role of a hard-nosed Texas ranger who joins forces with Rooster Cogburn (Jeff Bridges) and Mattie Ross (Hailee Steinfeld) to track down Mattie's father's murderer. Again, Damon shows skill as a jaded law enforcer who delights in verbally sparring with Mattie. Watching the two bicker is the secret joy on their journey to redemption.

Warner Bros./YouTube

5. Colin Sullivan (The Departed, 2006)

You've seen the movie. You know what it's about. You don't need a plot description, or even a love letter to Damon's work as a sneaky mole inside the Massachusetts State Police department. What's worth revisiting is that Damon's Sullivan demonstrates the danger of allegiances, whether they're to God or love interests or family. That's especially true if the family member in question is a mobster who jerks off in porno theaters. Masturbation and family ties aside, The Departed is everything you want in a gangster flick: profane, bloody, and shocking.

Paramount Pictures/YouTube

4. Tom Ripley, (The Talented Mr. Ripley, 1999)

Layabout 20-something Tom Ripley (Damon) is offered $1,000 to retrieve a dashing playboy named Dickie Greenleaf (Jude Law) from Italy. To put it mildly, this does not go quite as planned. Instead, Tom -- like any great chameleon -- becomes Dickie. He walks like Dickie. He talks like Dickie. He likes the same women as Dickie. Damon's eeriness and desperation are unsettling to watch as he slips deeper and deeper into the mind of a man gone crazy. Yet somehow, Ripley earns our sympathy. You feel bad for the poor guy who is ruining the lives of others. How does that work?

Miramax/YouTube

3. Mike McDermott (Rounders, 1998)

The movie that spawned a generation of good but mostly bad Texas Hold 'Em players who think wearing sunglasses inside a casino is the key to success. Yes, Rounders is a slick and revealing film about card sharks and underground poker houses, but it's the nuggets of wisdom that Damon and company intersperse throughout that make the movie. Anyone can tell a riveting story about the highs and lows of poker players. But what about the reality of a player like Mike, who is so addicted to the game that he chooses cards over lovers and forfeits his burgeoning career in law to sit in a room with a bunch of strangers for hours on end? Rounders neither disses nor praises gambling. It just lays it all out and lets the chips fall as they may.

Miramax/YouTube

2. Will Hunting (Good Will Hunting, 1997)

Each viewing of Gus Van Sant's masterpiece is just another reminder of how spellbindingly earnest this movie is. Damon, who won an Academy Award for co-writing the film with Ben Affleck, speaks from the heart in every single scene. Even as he's pushing away Robin Williams's bearded and bespectacled therapist, you understand the gut reaction, the instinct to escape pain, to run away and pretend like it doesn't exist. Will Hunting is a secret genius, but he's also just another insecure and afraid 20-something who desperately wants to be happy.

Warner Bros./YouTube

1. Mark Whitacre (The Informant!, 2009)

Hear us out: Damon truly delivers the most dynamic performance of his career in this Steven Soderbergh seriocomedy. Mark serves as an FBI informant, leaking his company's illegal activity to the government. Through his voice-over, the movie overwhelms viewers with comic observations about the mundane. There are more laughs in The Informant than 99% of all American comedies made these days, and its dramatic undertones work, too: watching Mark unravel as his lies stack up is difficult to stomach. Once again, Damon turns a criminal -- a man causing harm to his fellow citizens -- into a sympathetic hero. He's a pathological liar, yet you still want to believe everything he says.

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Sam Fragoso is the host of Talk Easy and a writer whose work has appeared in Vanity Fair, NPR, The Atlantic, and Playboy. He still truly believes We Bought a Zoo is better than Interstellar. Follow him and his other questionable opinions: @SamFragoso.

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