Matt Damon has had a remarkably rich film career, dating back to a bit part in Mystic Pizza, a quirky and charming movie that has always been one of my favorites. I’ve chosen several of his better known movies to introduce you to a range of his work.

Bourne Trilogy

First on the list: This excellent set brings together all three of the Bourne movies, the films that turned Matt Damon from a gentle, slightly wistful persona into the freakishly-tough (yet sensitive, naturally) action hero we now know & love.

The Bourne Identity

Freely adapted from Robert Ludlum’s 1980 bestseller, The Bourne Identity starts fast and never slows down. The twisting plot revs up in Zurich, where amnesiac CIA assassin Jason Bourne (Matt Damon), with no memory of his name, profession, or recent activities, recruits a penniless German traveler to assist in solving the puzzle of his missing identity. While his CIA superior (Chris Cooper) dispatches assassins to kill Bourne and thus cover up his failed mission, Bourne exercises his lethal training to leave a trail of bodies from Switzerland to Paris. Director Doug Liman infuses Ludlum’s intricate plotting with a maverick’s eye for character detail, matching breathtaking action with the humorous, thrill-seeking chemistry of Damon and Potente. Previously made as a 1988 TV movie starring Richard Chamberlain, The Bourne Identity benefits from the sharp talent of rising stars, offering intelligent, crowd-pleasing excitement from start to finish. –Jeff Shannon

The Bourne Supremacy

Good enough to suggest long-term franchise potential, The Bourne Supremacy is a thriller fans will appreciate for its well-crafted suspense, and for its triumph of competence over logic (or lack thereof). Picking up where The Bourne Identity left off, the action begins when CIA assassin and partial amnesiac Jason Bourne (a role reprised with efficient intensity by Matt Damon) is framed for a murder in Berlin, setting off a chain reaction of pursuits involving CIA handlers (led by Joan Allen and the duplicitous Brian Cox, with Julia Stiles returning from the previous film) and a shadowy Russian oil magnate. The fast-paced action hurtles from India to Berlin, Moscow, and Italy, and as he did with the critically acclaimed Bloody Sunday, director Paul Greengrass puts you right in the thick of it with split-second editing (too much of it, actually) and a knack for well-sustained tension. It doesn’t all make sense, and bears little resemblance to Robert Ludlum’s novel, but with Damon proving to be an appealingly unconventional action hero, there’s plenty to look forward to. –Jeff Shannon

The Bourne Ultimatum

The often breathtaking, final installment in the Bourne trilogy finds the titular assassin with no memory closing in on his past, finally answering his own questions about his real identity and how he came to be a seemingly unstoppable killing machine. Matt Damon returns for another intensely physical performance as Jason Bourne, the rogue operative at war with the CIA, which made him who and what he is and managed to kill his girlfriend in the series’ second film, The Bourne Supremacy. Now looking for payback, Bourne goes in search for the renegade chief of CIA operations in Europe and North Africa, partnering for a time with a mysterious woman from his past (Julia Stiles) and constantly–constantly–on the run from assassins, intelligence foot soldiers, and cops. Directed by Paul Greengrass with the director’s thrilling, trademark textures and shaky, documentary style, The Bourne Ultimatum is largely a succession of action scenes that reveal a lot about the story’s characters while they’re under duress. Joan Allen, Albert Finney, David Strathairn, Scott Glenn, and Paddy Considine comprise the film’s terrific supporting cast, and the well-traveled movie leads viewers through Turin, Madrid, Tangiers, Paris, London, and New York. Overall, this is a satisfying conclusion to Bourne’s exciting and protracted mystery. –Tom Keogh

Good Will Hunting

Robin Williams won the Oscar for Best Supporting Actor, and actors Matt Damon and Ben Affleck nabbed one for Best Original Screenplay, but the feel-good hit Good Will Hunting triumphs because of its gifted director, Gus Van Sant. The unconventional director saves a script marred by vanity and clunky character development by yanking soulful, touching performances out of his entire cast (amazingly, even one by Williams that’s relatively schtick-free). Van Sant pulls off the equivalent of what George Cukor accomplished for women’s melodrama in the ’30s and ’40s: He’s crafted an intelligent, unabashedly emotional male weepie about men trying to find inner-wisdom.

Matt Damon stars as Will Hunting, a closet math genius who ignores his gift in favor of nightly boozing and fighting with South Boston buddies (co-writer Ben Affleck among them). While working as a university janitor, he solves an impossible calculus problem scribbled on a hallway blackboard and reluctantly becomes the prodigy of an arrogant MIT professor (Stellan Skarsgård). Damon only avoids prison by agreeing to see psychiatrists, all of whom he mocks or psychologically destroys until he meets his match in the professor’s former childhood friend, played by Williams. Both doctor and patient are haunted by the past, and as mutual respect develops, the healing process begins. The film’s beauty lies not with grand climaxes, but with small, quiet moments. Scenes such as Affleck’s clumsy pep talk to Damon while they drink beer after work, or any number of therapy session between Williams and Damon offer poignant looks at the awkward ways men show affection and feeling for one another. –Dave McCoy

The Departed

No matter where you fall on the Scorsese appreciation scale, there’s no denying that The Departed is a signature piece of work from one of America’s finest directors, designed for maximum impact with a breathtaking series of twists, turns, and violent surprises. It’s an intricate cat-and-mouse game, but this time the cat and mouse are both moles: Colin Sullivan (Matt Damon) is an ambitious cop on the rise, planted in the Boston police force by criminal kingpin Frank Costello (Jack Nicholson). Billy Costigan (Leonardo DiCaprio) is a hot-tempered police cadet who’s been artificially disgraced and then planted into Costello’s crime operation as a seemingly trustworthy soldier. As the multilayered plot unfolds (courtesy of a scorching adaptation by Kingdom of Heaven screenwriter William Monahan), Costigan and Sullivan conduct a volatile search for each other (they’re essentially looking for “themselves”) while simultaneously wooing the psychiatrist (Vera Farmiga) assigned to treat their crime-driven anxieties.

Such convenient coincidences might sink a lesser film, but The Departed is so electrifying that you barely notice the plot-holes. And while Nicholson’s profane swagger is too much “Jack” and not enough “Costello,” he’s still a joy to watch, especially in a film that’s additionally energized by memorable (and frequently hilarious) supporting roles for Alec Baldwin, Mark Wahlberg, and a host of other big-name performers. The Departed also makes clever and plot-dependent use of cell-phones, to the extent that it couldn’t exist without them. Powered by Scorsese’s trademark use of well-chosen soundtrack songs (from vintage rock to Puccini’s operas), The Departed may not be perfect, but it’s one helluva ride for moviegoers, proving popular enough to become the biggest box-office hit of Scorsese’s commercially rocky career. –Jeff Shannon

Ocean’s Trilogy

Like the Bourne package, this trio of movies is brought together in one set, but it’s surprisingly not called Ocean’s 36 … I’ll have a word with the studio and get that fixed. Incorrectly named or not, the movies are still a silly and madly entertaining hodge-podge that’s all style and just enough substance to hold together.

Ocean’s Eleven

Ocean’s Eleven improves on 1960’s Rat Pack original with supernova casting, a slickly updated plot, and Steven Soderbergh’s graceful touch behind the camera. Soderbergh reportedly relished the opportunity “to make a movie that has no desire except to give pleasure from beginning to end,” and he succeeds on those terms, blessed by the casting of George Clooney as Danny Ocean, the title role originated by Frank Sinatra. Fresh out of jail, Ocean masterminds a plot to steal $163 million from the seemingly impervious vault of Las Vegas’s Bellagio casino, not just for the money but to win his ex-wife (Julia Roberts) back from the casino’s ruthless owner (Andy Garcia). Soderbergh doesn’t scrimp on the caper’s comically intricate strategy, but he finds greater joy in assembling a stellar team (including Brad Pitt, Matt Damon, Don Cheadle, and Carl Reiner) and indulging their strengths as actors. The result is a film that’s as smooth as a silk suit and just as stylish. –Jeff Shannon

Ocean’s Twelve

Like its predecessor Ocean’s Eleven, Ocean’s Twelve is a piffle of a caper, a preposterous plot given juice and vitality by a combination of movie star glamour and the exuberant filmmaking skill of director Steven Soderbergh (Out of Sight, The Limey). The heist hijinks of the first film come to roost for a team of eleven thieves (including the glossy mugs of Brad Pitt, Matt Damon, Bernie Mac, and Don Cheadle), who find themselves pursued not only by the guy they robbed (silky Andy Garcia), but also by a top-notch detective (plush Catherine Zeta-Jones) and a jealous master thief (well-oiled Vincent Cassel) who wants to prove that team leader Danny Ocean (dapper George Clooney) isn’t the best in the field. As if all that star power weren’t enough–and the eternally coltish Julia Roberts also returns as Ocean’s wife–one movie star cameo raises the movie’s combined wattage to absurd proportions. But all these handsome faces are matched by Soderbergh’s visual flash, cunning editing, and excellent use of Amsterdam, Paris, and Rome, among other highly decorative locations. The whole affair should collapse under the weight of its own silliness, but somehow it doesn’t–the movie’s raffish spirit and offhand wit soar along, providing lightweight but undeniable entertainment. –Bret Fetzer

Ocean’s Thirteen

It’s bolder. Riskier. The most dazzling heist yet. George Clooney, Brad Pitt, Matt Damon and more reteam with director Steven Soderbergh for a split-second caper that stacks the deck with wit, style and cool. Danny Ocean again runs the game, so no rough stuff. No one gets hurt. Except for double-crossing Vegas kingpin Willy Bank (Al Pacino). Ocean’s crew will hit him where it hurts: in his wallet. On opening night of Bank’s posh new casino tower The Bank, every turn of a card and roll of the dice will come up a winner for bettors. And they’ll hit him in his pride, making sure the tower doesn’t receive a coveted Five Diamond Award. That’s just the start of the flimflams. The boys are out to break The Bank. Place your bets!