Amongst his many leading-man roles, it’s telling that the first performance that always jumps to mind when I’m asked about Matt Damon is a small cameo. Amongst the drawn out visions of the life of the radical Cuban militant Che Guevera in Steven Soderbergh’s astonishing four-hour-long Che, Damon appears in the second movement of the film, for a moment, as a German priest attempting to strike piece between Benicio Del Toro’s Che and the Bolivians. Considering that Del Toro is the biggest name in the film otherwise, Damon’s appearance comes to signal something unexpected in a film that is, in its way, a consideration of the fight to get a personal film made and distributed in the modern marketplace. In the story, Damon was the comely, reasonable voice of peace, a symbol of compromise in a film about resisting compromise in the hopes of making something that is truly yours.

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Image via Universal Pictures

And as an actor, Damon has come to represent a career about compromise. Big-budget, left-leaning blockbusters figure into Damon’s oeuvre equally as much as smaller, more intimate projects that touch on personal political issues for the vocal movie star. Before Jason Bourne, his last two films were The Martian and Interstellar, two science fiction epics with humongous budgets and plenty of star power alongside him, but before that, he lent his talents to both Terry Gilliam’s bizarre The Zero Theorem and Gus Van Sant’s quite excellent Promised Land while also playing a whippersnapper in George Clooney’s deeply dull The Monuments Men and an unlikely action hero in Elysium.


Few major actors feel such a pressing need to work with artists both big and small, flush with cash and scraping by; his friend and writing partner Ben Affleck certainly hasn’t felt that need for awhile. There are plenty of benefits to this work philosophy for Damon, who has only indulged in auteur-led franchises like Bourne and Ocean’s Eleven thus far, but one is that he’s played a myriad of character types in a vast array of films that range from genre workouts to eyes-on-the-Oscar-prize dramas to grippingly personal true-life biopics. On the eve of Jason Bourne’s release, I thought I’d gather up his best work thus far that hasn’t been under director Paul Greengrass (or Doug Liman) in the Bourne films.

'The Informant!'

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Image via Warner Bros.

One thing that has become glaringly clear over the years since Good Will Hunting came out is that Matt Damon is one hilarious motherfucker when he wants to be. His work with Jimmy Kimmel on Jimmy Kimmel Live! has often been uproarious, and his sarcasm in The Martian made for a handful of memorable deliveries, but these are largely done without emotional stakes, which great comedy requires. To see him truly throw himself into the world of a fool, one need look no further than this inexplicably ignored gem from Steven Soderbergh, in which Damon plays a dimwitted, overtly willing corporate spy tied to the corn industry. It’s difficult to summarize just how staggeringly funny this movie is, but its even harder to convey just how devastating Damon’s portrayal of Mark Whitacre is at the end of Soderbergh’s film. There’s a rueful undercurrent to the film that carries a venomous view of corporate criminals, but Damon’s performance strikes at a painful kind of ambition – the wanting to do some good in the world while also benefitting from the very worst of society at large.

'Invictus'

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Image via Warner Bros.

Full disclosure: I love Clint Eastwood as a director. As a performer, he’s hit and miss but as a director, he calls upon a recollection of old Hollywood that informs his aesthetic and pacing but has a long history of disrupting that classicism in his choice of story and his visible attention to personal details. Invictus is a perfect example of how he makes run-of-the-mill real-life material into something far more distinct and intimate, turning the story of the South-African rugby champions into a master class in political maneuvering and intellectual showmanship. Here, Damon plays rugby team leader Francois Pienaar, who is asked to win the Rugby World Championship by South Africa’s newly appointed president, Nelson Mandela, played with surpassing gravitas and unexpected humor by the inimitable Morgan Freeman.

Freeman’s Mandela, like Eastwood, knows that the world understands wins in entertainment and athletic talent over political urgency, and sees the Rugby game as a way to signal that he is a good leader and that South Africa is worthy of worldwide consideration after the scarring horrors of Apartheid. So, Pienaar becomes the vision of national pride and white hope for Mandela, and it’s to Damon’s credit that he both nails the accent and gives the character notes in delivery and gesticulation that suggest a pensive, active inner life. Damon’s interactions with Freeman are wonderfully wandering in trajectory, evoking a sense of two resourceful, well-known men getting to know one another, and of a political leader crafting his still-malleable image.

'Contagion'

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Image via Warner Bros.

I had to limit my Soderbergh-Damon pairings to two – Behind the Candelabra and Ocean’s Eleven lost out here. Contagion should have been the movie that put Soderbergh back up at Ocean’s Eleven level but, alas, it was not. The director’s vision of a fast-killing, flu-like disease spreading in America in the days of social media and camera phones doesn’t necessarily center on Damon but he remains the anomaly: The Man Who Can’t Get Sick. He keeps his life and a sizable portion of his sanity while people at the CDC can’t say the same. Damon’s performance could be dismissed as an everyman caricature but he gives such feeling to the character, with small, smart moments: the way his face cheers up when he sees his daughter at the hospital, that devastating “What happened to her?” line, the way he looks at the photos of his late wife (Gwyneth Paltrow). The film is a fair, unsparing take on what the next extinction event would likely look like, if not by bomb or comet, and in Damon we see the practical man left to wonder about what happened, and how everyone else reacted when things got truly dire.

'The Talented Mr. Ripley'

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Image via Paramount

Okay, so it’s not quite as good as Wim WendersThe American Friend, but not many neo-noirs and murderous thrillers are quite as good as that film on the whole. Anthony Minghella’s film has a certain classicism –the influence of Rossellini’s visions of Italy are impossible to miss - but there’s also something menacing and melancholic about this story of a sad, deadly impersonator named Ripley. It would be unfair to compare Damon’s Ripley to either Dennis Hopper’s venomous take or the icy, extraordinary work that John Malkovich makes of the character in Ripley’s Game for several reasons, but mostly because they are different stories. The American Friend and Ripley’s Game are about male competition when you get down to the bone, but The Talented Mr. Ripley is a tale of heartache and it's in Damon’s youthful gaze that the real hurt of the thing lies. We see him do quite a few cruel, even homicidal acts but there are undercurrents of shame, sexuality, and class warfare at work in the film and in Damon’s performance, which seemingly confirmed his staying power following his breakout performance in Good Will Hunting.

'Good Will Hunting'

Speaking of which! One simply cannot ignore the film that brought Damon out into the spotlight, and to its credit, the film is still an absolutely gorgeous piece of work. Gus Van Sant has been making some of the most endearingly anxious, and intimately political films of the last few decades, and this was proof that his visions were more palatable to the masses than anyone who saw Mala Noche or the masterful My Own Private Idaho could have imagined. It’s one of those films where everything is just a little rougher and pensive than you’d think: Van Sant captures a Boston that is both brilliant and stereotypically brutish, vistas that range from laughably dilapidated to tidy to impressively sprawling, such as the highway shot that ends the film.

The script, by Damon and Affleck, has the slang down, but also has a clear comfort with the places, with the corners of these neighborhoods that other films would gloss over. The film gives Boston a sense of character that hasn’t been seen since small masterworks like The Friends of Eddie Coyle, but more than anything, it’s the acting. Minnie Driver made a quick impression, and there’s simply nothing but praise that can be given to what the late Robin Williams does with the character of the bemused and bruised psychiatrist, but it’s Damon who anchors this surprisingly loose yet sharply comprised drama. He makes the titular troubled genius feel like an actual discovery; a warm, funny, young wonder battered into believing he’s just one of the guys, and as such, the film continues to feel like a hidden gem, even after the Oscar wins and canonizations.

'The Departed'

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Image via Warner Bros.

Unpopular opinion: I think The Departed is probably the least substantive film Martin Scorsese has made over the last 16 years. Despite some heady, cerebral thematic concepts and some remarkable political and societal observations, and the formal ingenuity we’ve come to expect from the unparalleled American master, it’s a little too beholden to genre to be in the same mix as out-and-out groundbreakers like The Wolf of Wall Street, Hugo, and the shattering Shutter Island.

This isn’t to say I don’t love the film. It’s a better film, on almost every level, in comparison to the original Infernal Affairs, a strong genre workout starring Andy Lau, and the acting is giddily exaggerated, bordering on the knowingly cartoonish. Scorsese catches violence as a kind of madness, one that makes duplicitous madmen out of the men who enact it and heartless obsessives out of the people who try to control it. It’s a perfect place to set a film about two men fighting against their invented identities, and as much as Leonardo DiCaprio in the role of the cop undercover in the gang, Damon nails the paranoia, power-hunger, and self-confidence that scratch away at his image as an upstanding cop who is, in reality, reporting back to the King Lizard that is Jack Nicholson.

The fact that DiCaprio gets shot is almost the easy way out in this case. Damon fearlessly becomes a sniveling, desperate mess clinging to the small modicum of a life he has before Mark Wahlberg walks in with the plastic-wrapped shoes. The actor expertly conveys the power and the panic that comes from keeping up a veneer of normalcy when you’re increasingly aware of the rot you’re covering up.

'Interstellar'

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If Christopher Nolan’s science fiction epic had found a way to end around the same time Matt Damon’s character is quelled in Interstellar, it would be amongst the most celebrated science fiction films of the decade. It might be anyway, unbeknownst to me, but Nolan’s attempts to push in an allegory for being a father away from his children made the film feel sentimental and self-important in the absolutely most familiar and manipulative of ways. And there’s really no way for me to convey to you how exhilarated I was with this movie up to and including when they discover Damon on the planet with the ice clouds or whatever the hell is going on in that sky. The imaginative way that Nolan denotes each world is undercut by his incessant need to follow conventional story structures, aiming to reunite the hero-genius father with his heroine-genius daughter (Jessica Chastain), no matter how forced or uninspired it feels after facing worlds with monsoon-like waves on the regular and, ya know, black holes.

The villainous turn that Damon gives here calls the film back to its roots in pulp, creating the character through wardrobe and small tics in delivery and physicality that never overplay the tortured animal beneath Damon’s explorative doctor. His exchanges with Matthew McConaughey and crew gives the film real tension and a too-rare feeling of the very real madness that space can so easily bring on.

'True Grit'

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Image via Paramount Pictures

The Coen brothers outdid Henry Hathaway’s original with this 2010 remake on nearly every level that can be counted. The pickled Coen humor is rampant, as is the attentive, unique production design and the eloquent, hypnotic editing and composition that one can be seen in every sequence. The film looks better and certainly sounds better, with Jeff Bridges’ warm, crackling yelps and grumbles unseating John Wayne’s impersonal crispness. And in the role of LaBeouf, originated by musician Glen Campbell, Damon creates a uniquely stately yet morally dubious character of little charm but tremendous fascination. One can blame the time period for the character coming onto Hailee Stanfield’s young heroine, but Damon both makes the flirtation plausible and retains some sense of respectability for the lawman who joins up with Rooster Cogburn and Mattie Ross. The mustache is a hoot, and Damon conjures plenty of other sight gags that could have gone by without a thought in lesser performers’ hands. In Damon’s take, LaBeouf becomes as mythic and gregarious a character as Rooster in his own distinct way.

'Margaret'

Kenneth Lonergan's Margaret, the playwright-director's long-awaited follow-up to his extraordinary debut, You Can Count On Me, is likely one of the best films of this decade that you've never seen. Given an abbreviated, quickly shuffled along release in L.A. and New York, Lonergan's sophomore effort became a cause for many esteemed critics, including The New Yorker's Richard Brody, to the point that the film came back for an extended run. If you haven't seen this masterwork yet, it's one of those films that immediately makes an impression and the fact that the cast is packed with tremendous actors, including Mark Ruffalo, Allison Janney, Anna Paquin, Jeannie Berlin, Jean Reno, John Gallagher, and J. Smith-Cameron, should make the fact that it remains largely unknown all the more confounding.

Damon's role doesn't factor into the astonishing inciting incident - a bus accident a little north of Manhattan's Lincoln Center - but he is key factor in the aftermath of the accident that lands at the feet of Paquin's unlikely teenage heroine, Lisa. As a flirtatious teacher at Lisa's school, he represents the promise and assuredness of adulthood but Damon plays the role as a conflicted, alluring middle-aged man rather than just a symbol. I'd rather not give away the part he plays in this sprawling, sensational New York melodrama and it's easy enough to say that his character comes to highlight the faultiness of the doctrine of age as wisdom, much like Lisa's father, played by Lonergan himself. This is the kind of propulsive dramatic work that I wish I saw Damon in more often, giving a deeply human performance that neither leans too hard on "realism" nor goes overboard with the theatricality.

'The Good Shepard'

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Image via Universal

Robert De Niro's sophomore feature as a director was largely derided for its extended runtime and its ruminative placidity but subsequent appraisals have rightly nailed it as a fascinating if imperfect vision of the coldness of dispassionate work. Damon's increasingly unnerving performance as Edward Wilson, one of the founding members of the C.I.A., strikes at the heart of De Niro's feelings about governmental institutions and developed bureaucracy. The icy chill of De Niro's visual atmosphere that runs throughout the film's 207 minutes reflects the studious, control-obsessed Wilson, and when the character is put in a cage with his wife, Margaret (Angelina Jolie), you can see De Niro's dubious opinion of a government that's run only by facts and information, ignoring the emotional implications of what their work often does. Damon's performance is cold yet driven, suggesting the same furious yet required repression that seemed to keep Leonardo DiCaprio's J. Edgar Hoover in governmental line in Clint Eastwood's majestic J. Edgar, and The Good Shepard, though a far lesser film, comes to embody a similar kind of horror.