“Good Will Hunting” (1997)
There are “auspicious debuts” and then there is “Good Will Hunting.” Although Damon had appeared in a handful of films before his screenwriting debut (including “Mystic Pizza” and “School Ties”), “Good Will Hunting” effectively stands as his coming out party. Written by Damon and best pal/fellow actor Ben Affleck, the film was wisely helmed by Gus Van Sant and bolstered by a supporting performance by Robin Williams. Damon has a knack for being open and relatable on-screen, but that specific charm is on full display in the heartfelt drama, and Damon isn’t afraid to lay it all on the line. How about them apples?
Casting Damon alongside Edward Norton was a major stroke of genius in this literally high-stakes poker drama from director John Dahl. As card shark pals from way back, Damon and Norton bounce and blast off of each other with electric regularity, a chemistry played to the hilt with snappy dialogue, well-paced sequences and Damon frequently edging into ever-darker territory.
“The Talented Mr. Ripley” (1998)
Damon got chameleon-like with his other big 1998 feature, a tricksy take on Patricia Highsmith’s similarly wicked novel of the same name. Anthony Minghella’s slippery and twisting tale of mistaken (and stolen) identities, hidden desires and a generous dash of heart-stopping crime lives and dies with Damon’s performance as the talented Mr. Ripley, a Princeton man with a pedigree — except, well, wait, that’s not the case, he’s just a hanger-on looking for a buck or a lonely guy looking for a pal or something far more nefarious. Damon’s most finely tuned work holds up in a big way, and if you never know where you stand with regards to his Tom Ripley, then he’s done his job.
“The Bourne Identity” (2002)
“The Bourne Identity”: Because you have to choose at least one of Damon’s calling-card action hero roles, so why not turn back to the first offering — complete with Moby-styled jams — to reflect on Damon’s enviable transition from solid actor to actual movie hero. His Jason Bourne might not know who he is, but Damon is fully in control here, marrying charm with character and action with brains.
“The Departed” (2006)
If you’ve got any doubts that Damon absolutely excels when he’s matched up with other talented actors, look no further than “The Departed,” which sees him facing off with Leonardo DiCaprio, Jack Nicholson, Alec Baldwin, Mark Wahlberg and Martin Sheen (and Vera Farmiga, for the necessary feminine touch), as directed by Martin Scorsese. Marty has some fun playing his actors against type in the twisted and gritty cops-and-mobsters drama, with a grizzled DiCaprio cast as the secret good guy and Damon relishing the chance to play bad (while also playing good — again, it’s twisted). Another actor might have chewed up the scenery a touch more, but Damon finds other ways to grab hold and not let go, even when we can’t help but root against him.
“The Informant!” (2009)
Despite his serious actor jobs and action man pedigree, Damon knows how to get goofy and doofy when the project calls for it — hello, Linus Caldwell — so it’s only natural that he would use those muscles alongside a director who can also slip between genres with ease. For “The Informant!,” Damon is asked to play mostly dumb for Steven Soderbergh, who seems to revel in the dimwittedness that Damon shines out so brightly. The whole hangs on apparent unwittingness, but Damon and Soderbergh know exactly what they’re doing. It’s (maybe, probably) Damon’s funniest film role yet.
“The Adjustment Bureau” (2011)
It’s one for the romantics. Damon has starred alongside plenty of powerful leading ladies, but he’s never been able to match the chemistry on display with his “Adjustment Bureau” co-star Emily Blunt, as the duo are forced to battle space, time and weird strangers in hats to be together in this dazzling take on the short story by Philip K. Dick. Despite a stellar enough opening weekend and generally positive reviews, the film has been a mostly overlooked entry in Damon’s filmography. It’s a shame, though, because it’s easily his most romantic turn yet, the kind that puts a truly fresh spin on the often done-to-death theme of “love conquering all” (especially hats).
“Behind the Candelabra” (2013)
For one of Steven Soderbergh’s most glitzy — and gold and glamorous and actually shiny — TV outings, he turned to a familiar face: Damon, cast as Liberace’s (Michael Douglas) much younger (and, comparably, much dumber) boyfriend, Scott Thorson. Damon slips back into Soderbergh’s style and humor without missing a (piano) beat, but he gives real pathos to Thorson, infusing him with just enough humanity and heart to make a mostly out-there romance work.
“The Martian” (2015)
Damon’s most recent turn as a marooned astronaut who is forced to survive solo on the Red Planet after he’s left behind by his good-intentioned crew (they thought he was dead, you can’t really blame them for the gaffe) is one of his best performances yet, a funny, brave and totally consuming feat of acting that elevates Ridley Scott’s feature to new heights. It just may be the greatest argument yet for Damon’s status as a bona fide movie star — after all, who else could make such a part (and such a movie) so seriously engaging and weirdly life-affirming? (No, we’re not forgetting about Sam Rockwell, promise.)