Since earning his career breakout with Good Will Hunting in 1997, Matt Damon has won an Academy Award, worked for some of the finest directors (and alongside some of the most talented actors) in Hollywood, and proved his mettle as a dramatic actor, gifted screen comic, and steely action hero. In honor of his latest starring role, in Ridley Scott’s The Martian this weekend, we decided to rifle through the Damon filmography and take a closer look at the ten most definitive entries. Which of your favorites made the cut? Which ones have the critics blasphemously overlooked? There’s only one way to find out!
Think you’re committed to your job? Try being Matt Damon in preparation for Courage Under Fire. For his role as Specialist Ilario, Damon dropped 40 pounds, adopting a grueling training regimen that had him running miles a day and subsisting on a diet consisting of little more than cigarettes and coffee. It was not, as you might imagine, a decision popular with Damon’s doctors — or, more importantly, his body, which required no small amount of medical repair after shooting ended. But all’s well that ends well, and Edward Zwick’s Rashomon-style Gulf War drama helped Damon break the dry spell he’d been suffering since nabbing a role in 1993’s Geronimo: An American Legend. Oh, and the critics liked it too — critics like Steve Rhodes, who called it “An extremely moving picture that left me with my heart racing and my arms clutching myself and staring at the screen.”
Before you even opened this list, you probably knew we’d end up here. And for good reason: Good Will Hunting is not only the massive left-field success that launched Damon and his pal/co-writer Ben Affleck into the Hollywood stratosphere, it’s a smart, tenderly written tale of the ways love and friendship can help build a bridge between the memories that haunt us and the futures we dream of. With empathetic direction from Gus Van Sant, beautiful music from Danny Elfman and Elliott Smith, and an Oscar-winning supporting performance from Robin Williams, Good Will Hunting was the kind of film that played equally well to the arthouse and cineplex crowds — and the kind of story that makes you feel good about loving movies. As Margaret McGurk of the Cincinnati Enquirer put it, “Good Will Hunting is another auspicious sign that the best of Young Hollywood is not only bringing back respect for the craft of acting, but for the cogent telling of tales as well.”
Between Good Will Hunting and The Rainmaker, Damon had a pretty good 1997, and seemed poised to continue his winning streak with 1998’s Rounders, a gambling drama about a law student whose efforts to give up high-stakes backroom poker in order to appease his girlfriend (Gretchen Mol) are complicated by the arrival of a ne’er-do-well buddy (Edward Norton) who needs his help to making enough scores to pay off a massive debt owned by a local mobster (John Malkovich). In spite of a nifty premise and a cast loaded with young Hollywood up-and-comers, Rounders went bust at the box office, although it’s since gone on to acquire something of a cult status on the home market (and rumors of a sequel even made the rounds a few years ago). “You’re going to hear a lot about the good job Edward Norton and Gretchen Mol do in Rounders,” predicted Edvins Beitkis of the San Francisco Examiner. “But the movie lives and dies with Matt Damon.”
As conceived by author Patricia Highsmith, Tom Ripley is a deeply unsavory character — a psychopath who uses his natural charm and malfunctioning moral compass as the gateway into a lavish lifestyle built on lies, theft, and murder. Not the kind of role you’d expect to go to a wholesome-looking fellow like Matt Damon, in other words — but that’s part of what made Damon’s performance in Anthony Minghella’s The Talented Mr. Ripley so profoundly disquieting. Capable of communicating bottomless need, desperate rage, and cold calculation in a single scene, Damon proved his range was far greater than many may had suspected. “We all knew Damon was a fine actor after Good Will Hunting,” wrote Jeffrey Westhoff of the Northwest Herald, “but The Talented Mr. Ripley takes him much further much faster than anyone could have expected.”
The occasional odd cameo aside, it’s generally safe to say Matt Damon is usually the biggest star in any movie he makes — but the Ocean’s trilogy is a cheerful exception to that rule, boasting an overstuffed cast full of film stars that includes George Clooney, Brad Pitt, Julia Roberts, Elliott Gould, Don Cheadle, Catherine Zeta-Jones, Al Pacino, Carl Reiner, and Bernie Mac… just to name more than a few. As Linus Caldwell, the master pickpocket in the team of thieves assembled by the impossibly suave Danny Ocean (Clooney), Damon got the chance to lend comic relief, perform some nifty cinematic thievery, and just generally make it all look easy while sharing the load with the cast of a lifetime. In the end, after three films of watching Ocean and his gang make off with millions in ill-gotten loot, it was the audience who made out best of all; as Rene Rodriguez wrote of 2007’s Ocean’s Thirteen for the Miami Herald, “When a movie keeps you this entertained without insulting your intelligence, it’s hard to complain.”
It seems laughable now, but before The Bourne Identity reached theaters, there were a lot of people who didn’t think Matt Damon had what it took to be a convincing action hero. Those doubts were quickly erased with director Doug Liman’s sleek, powerful adaptation of the Robert Ludlum novel — a huge box office hit that was powered with equal parts explosive set pieces and a solid central performance by its star. As it turned out, Damon had not only the dramatic chops to realistically portray the fear and confusion of an amnesiac who slowly begins to realize he’s a lethal assassin, but the physical presence to make audiences believe he could kill a man with a pen — and launch a franchise that has had filmgoers lining up to follow a global trail of high-speed car chases, conspiracy cover-ups, and hand-held cameras shakily capturing some truly impressive hand-to-hand combat. “Who needs an identity,” quipped Peter Keough of the Boston Phoenix, “when you’re having this much fun?”
Damon’s had a number of opportunities to show off his comedic chops over the years, but he’s rarely gone for all-out comedy — which is why, despite its 60 percent Tomatometer, we decided to include 2003’s Stuck on You here. Co-starring Damon and Greg Kinnear as conjoined twins who reach a crossroads when the more outgoing twin (Kinnear) decides to pursue his Hollywood dream, this Farrelly brothers production lacks the gleeful ribaldry that defined their earlier efforts, but in its absence, viewers are able to focus on the genuine sweetness beating at the heart of their films’ best moments — and that, coupled with Damon and Kinnear’s easy chemistry, is just enough to make it one of the more appealing efforts in a filmography that’s largely fallen prey to the law of diminishing returns. As Claudia Puig wrote for USA Today, “Not only is Stuck on You a hoot, but it also walks a line — as the best Farrelly brothers movies do — between silly farce and sweet sentimentality that artfully avoids the cloying or maudlin.”
Violent, bleak, and unbearably tense, The Departed earned director Martin Scorsese his long-overdue Best Director Oscar — but before that, it delighted critics and filmgoers by using Andrew Lau and Alan Mak’s Infernal Affairs as the launchpad for an unflinching look at the personal toll exacted by the mortal struggle between law enforcement and organized crime. As dirty cop Colin Sullivan, Damon gives one of his subtlest and most heartbreaking performances, portraying a man who knows he’s living one step away from prison — or worse — and who you can’t help but feel for, even as he works to ferret out the identity of Mafia mole and honest cop Billy Costigan (Leonardo DiCaprio). Though some critics compared The Departed unfavorably to Infernal Affairs, most agreed with the Academy voters who named it the year’s Best Picture; in the words of Beyond Hollywood’s Brian Holcomb, “Scorsese has made an incredible cover version of the original, imbued with every ounce of his artistic personality transforming it into something both familiar and new.”
Life as an action hero seems like fun, but every actor wants the chance to demonstrate diversity, so after a few years of beating people up as Jason Bourne, Damon grew a mustache and a paunch for Steven Soderbergh’s The Informant!. The strange-but-true story of Mark Whitacre, who blew the whistle on price fixing at Archer Daniels Midland and worked as a secret FBI informant while embezzling millions from the company (and experiencing an acute mental breakdown along the way), Informant! allowed Damon to indulge his inner delusional schlub without losing sight of Whitacre’s essential humanity; instead of the cruel display it could have been, the movie’s a sensitive — yet still absurdly funny — satire of modern capitalism. “As Soderbergh lovingly peels away veil after veil of deception, the film develops into an unexpected human comedy,” observed Roger Ebert. “Not that any of the characters are laughing.”
A longtime passion project for director Steven Soderbergh, Behind the Candelabra languished in development limbo for years while the Oscar-winning filmmaker struggled to find funding for a drama depicting the last years of the flamboyant pianist Liberace, as told through his estranged ex-lover Scott Thorston. Even with Michael Douglas attached as Liberace and Damon on board to play Thorston, Candelabra remained stuck until HBO stepped in to cover the budget — and ended up reaping record ratings for a TV movie on the way to achieving major awards recognition, including an Outstanding Lead Actor Emmy nomination for Damon. (Douglas, meanwhile, won Outstanding Lead Actor, while Candelabra itself walked away with Outstanding Miniseries or Movie.) “Douglas is more than acceptable, but Damon has made an unforgettable character,” wrote David Thomson for the New Republic. “Scott Thorson is unknown and he comes out of the dark as the story that needs to be told.”
