9. “Margaret” (2011)
If all had gone to plan, Kenneth Lonergan‘s superb “Margaret” would have been released the same year as threequels “Ocean’s Thirteen” and “The Bourne Ultimatum,” making 2007 a neat microcosm of Damon’s varied talents. But it didn’t shake out that way, and when “Margaret” finally slunk out four years later, it vanished. It’s an enormous shame for everyone concerned, particularly Lonergan and extraordinary main star Anna Paquin, but also for Damon. As Aaron, the math teacher on whom the keenly outspoken Lisa (Paquin) develops a crush, he’s hardly the focus of the picture, but his role is no less complex for being a supporting turn. Akin to the subversion of his persona he achieved in “The Talented Mr. Ripley,” there is an element of conflict here —however much Lisa’s behavior is at fault, Aaron essentially abuses his position and exploits her precociousness. But somehow it doesn’t make us think of Aaron as a monster, or even a closet pervert: Damon’s everyman quality makes a much wider statement about the shameful acts that a facade of respectability might hide, even from the people themselves. In this subtle performance, there is a much more unsettling idea than “bad people might lurk amongst regular people.” It’s that there may not actually be such a thing as “regular.”
8. “Good Will Hunting” (1997)
There’s really no way that “Good Will Hunting” should have worked. A spec script written by two handsome rising actors about a blue-collar Boston kid working as a janitor at M.I.T. who happens to be a secret genius (and who, in the original script, is targeted by the FBI). It sounds like a ludicrous wish-fulfillment vanity project, and maybe in some hands it might have been, but somehow “Good Will Hunting” turned out to be a genuinely affecting little film that became a surprise smash (and won Damon and his co-writer Ben Affleck Oscars for Best Original Screenplay). The writing has a deep-set humanity that transcends the sillier moments, and director Gus Van Sant keeps it nicely grounded, but it’s the performances that make it fly, Damon (and Robin Williams) in particular. Will could be a sort of Mary Sue figure, but Damon makes him both realistically prickly and pleasingly vulnerable, a kid who might have more education than most people could ever dream of, but remains a scared little boy inside. The film would be a nightmare if you didn’t care about its title character, and in Damon’s hands, you would never dream of not rooting for him.
7. “True Grit” (2010)
It’s not the showiest or even the most nuanced character in the Coen Brothers’ hugely enjoyable “True Grit” remake, but Damon’s dickish Texas Ranger LeBoeuf still manages to be an indelible oddball. Between his typically Texan self-aggrandizing, the marble-mouthed cadence that he adopts after he’s partially bitten off his tongue, and his combination of heroic tendencies and borderline cowardice, Damon makes the role totally unforgettable, and he cannily steals the film away even from lead Jeff Bridges. He’s at once a total buffoon (there’s something brave about an actor who lets himself be so comprehensively outsmarted by a girl a third his age) and a thoroughly decent man. And that’s a combination that feels very Coen-ish, as well as a shame that he hasn’t yet reunited with the Brothers since (though he’ll at least be working from one of their scripts by year’s end, in George Clooney’s Coen-penned noir “Suburbicon”). Hilariously, Damon also confessed that his performance was essentially an impersonation of Tommy Lee Jones, the man currently hunting him in “Jason Bourne.”
