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The Films Of Matt Damon: A Retrospective

The Films Of Matt Damon: A Retrospective

We know it’s a little premature to start ruminating on the career of Matt Damon who, at the age of 40, is just entering the middle of his career. But as one of the biggest stars on the planet, a look at his work up until now is quite remarkable and pretty much unmatched by anyone his age in Hollywood. You wouldn’t have thought it watching his first, small appearance over 20 years ago in ‘Mystic Pizza,” but Matt Damon has evolved into one of the biggest and the most interesting movie stars in America. Even a decade ago, it looked as though his best friend and co-writer of “Good Will Hunting,” Ben Affleck, was set to be the breakout; Damon made a serious of unfortunate film choices, and his career was somewhat on the ropes.

But “The Bourne Identity” turned things around, and ever since then, Damon’s been committed to, and more importantly, had the requisite commercial heat to pick interesting roles and work with great directors — Steven Soderbergh, Terry Gilliam, Clint Eastwood and Martin Scorsese among them. He’s got the everyman Gary Cooper-esque charm of the great stars, but it’s when he subverts that appeal that he proves that he’s not just a movie icon, but a tremendous actor as well.

The Adjustment Bureau” hits theaters tomorrow, and we were pleasantly surprised to find that despite our fears over the project, which was delayed nearly nine months from its first mooted release date, the film is offbeat, interesting and mostly well-executed, and features yet another solid performance from its star. In honor of its release, we’ve gone back and taken a look at the career of a man who’s becoming, for the most part, a seal of quality.

Courage Under Fire” (1996)
Damon had popped up in various films before, most notably the coming-of-age tale “School Ties” but he really grabbed people’s notice for the first time in Ed Zwick‘s military thriller “Courage Under Fire.” The young actor, then only 25, underwent a dramatic, Christian Bale-style weight loss of 40 pounds for his role as Specialist Ilario, the medic of the Gulf War unit whose late leader (Meg Ryan) is being considered to be the first woman to be awarded a posthumous Medal of Honor. But the survivors have a secret, and Damon does excellent work as the guilt-ridden, drug-addicted soldier. It’s no wonder that his method commitment landed him the lead in Francis Ford Coppola‘s “The Rainmaker.” The film is one of Zwick’s more palatable efforts, content to be a thriller first and a polemic second, but it’s best remembered now for that early performance from Damon. [B-]

Good Will Hunting” (1997)
Not only was this the film that launched Matt Damon into the mainstream film world, but it also demonstrated how powerful an actor he already was, not to mention what he would become. Playing a South Boston mathematics savant with a criminal background full of physical and psychological abuse, Damon takes on the role of Will Hunting with aplomb. We always believe him as he plays the rock hard exterior with the soft, mushy guy waiting to break out from inside. It doesn’t hurt that the screenplay is magnificent, and Damon co-wrote it with Ben Affleck, meaning he makes every line count. He’s also never more convincing than when playing a character from Boston — the place is clearly in his blood. Perhaps most impressive is the way he plays against the other actors — it’s not surprising that he’s got chemistry with best pal Affleck, but to stand up against an Oscar-winning Robin Williams and the excellent Stellan Skarsgård takes some chops. You suspect that, without Damon in the lead, it wouldn’t be regarded as one of the best films of the 1990s. [A]

Saving Private Ryan” (1998)
In the summer of 1998, just a few short months after winning the Oscar for Best Original Screenplay for “Good Will Hunting,” Matt Damon and Ben Affleck’s next films would show just how divergent their career paths would become. Damon’s next project was a supporting part in Steven Spielberg’s WWII epic, while Affleck’s was a starring role in Michael Bay’s giant asteroid film “Armageddon.” Though his character’s name is in the title, Damon’s role, though integral, was truly a supporting one, not appearing in the film until an hour and 46 minutes in. Despite his lack of screen time, Damon leaves a strong impression in the film thanks to a monologue about his brothers that was apparently improvised by Damon. The rest of the ensemble, headed up by Tom Hanks, was filled out with a mix of character actors and up-and-comers like Edward Burns, Tom Sizemore, Barry Pepper, Adam Goldberg, Vin Diesel, Giovanni Ribisi, Jeremy Davies and Paul Giamatti, among others. Spielberg’s film, for which he won his 2nd Best Director statuette, has not aged entirely gracefully. The present day bookends are the director at his most cloyingly sentimental, but the D-Day landing at Normandy still ranks as one of the most chaotic, visceral depictions of war ever put on film. [B+]

Rounders” (1998)
Matt Damon‘s first lead following the success of “Good Will Hunting,” “Rounders” was mostly ignored on its debut, but has evolved into something of a cult hit over the years. The actor plays Mike, a poker whiz who’s promised his girlfriend (Gretchen Mol) that he’ll give the game up and focus on his law school studies. But when his no-good best pal Worm (Edward Norton) is released from prison, he’s dragged back into gambling to save his pal from the sinister Russian mobster Teddy KGB (a ludicrously enjoyably over-the-top John Malkovich), the same man who ended Mike’s career years earlier. While it’s beloved most by poker fans (it’s probably the best depiction of the game to date), the film in general is firmly entertaining — director John Dahl gives a terrific noirish tinge to the film, the script is zingy, and most of the performances — Norton and John Turturro in particular — are excellent. If the film has a flaw, it’s actually Damon; like many of his earlier films, he’s engaging, but a little bland. Still, we’d certainly be keen to see the long-promised sequel, if it ever materialized. [B]

The Talented Mr. Ripley” (1999)
It would have been just too easy for Matt Damon to trade in on his matinee idol good looks and collect paychecks for action movies and rom-coms. Instead, he pushes himself to physically disappear into his psychologically complex roles, using physical characteristics — a paunch, a crew cut or a pair of horn-rimmed glasses — as his entry into such enigmatic characters. His glasses are the totem of Tom the imposter in “The Talented Mr. Ripley,” the transformative role as the insidious grifter that announced Damon as a serious thesp, no vain pretty boy. Your average actor wouldn’t necessarily choose to take on the role of the homicidal sociopath in a gay panic, but Damon’s not your average actor. He’s made a practice of playing characters in identity crisis (“Good Will Hunting,” ‘Bourne,’ “The Informant!”) and ‘Ripley,’ was one of the first times he displayed his true virtuosity in embodying this conundrum. Damon’s most indelible characters are always striving to achieve some station in life that is almost impossible for them to gain, and Tom Ripley is the ultimate showcase for his ability to display the many emotional states of such nuanced, complicated people. He is simultaneously dorky, naive, seductive, hopeless, creepy and terrifying in Anthony Minghella’s adaptation of the Patricia Highsmith novel; the different emotions effortlessly cascading across his face. Damon is the type of post-modern actor that turns up his snub nose at the idea of a star persona and lets the characters completely take over, and ‘Ripley’ was his definitive announcement that he was here to ACT, not be a movie star. [A]

The Legend of Bagger Vance” (2000)
Though Damon was the star of this film, Robert Redford’s story about a famous golfer from Savannah, Georgia, really showcased Will Smith in his first purely dramatic role. Damon’s character Rannulph Junuh has lost his mojo after serving in the war, and with Charlize Theron as the love interest, one might think that the cast, along with Redford’s direction, would elevate this film to an elite status. However, the script was poor, and all of the actors, maybe with the exception of Smith, seemed to be cashing in mediocre performances (and don’t even mention those horrific accents!). It’s a sappy film with almost nothing going for it, except that everyone looks really pretty. Not one of Damon’s finest choices, but he rebounds easily in the next few years [D]

Ocean’s Eleven/Twelve/Thirteen” (2001/2004/2007)
Earmarked for Mark Wahlberg, the part of young pickpocket Linus seemed just as malleable as the rest of the skimpy characterizations in Steven Soderbergh’s heist movies, which were tailor-made for the stars’ sensibilities. Given that Damon has a less-defined screen presence than George Clooney and Brad Pitt, it became a bit unusual to see him consistently painted as the young, inexperienced member of the group, particularly after the ‘Bourne’ films. Still, Damon has some of the best moments in the three films, reminding Clooney about batteries in part one, mangling Robbie Coltrane’s impenetrable codespeak in the second film, and employing the ‘Gilroy’ nose to seduce Ellen Barkin in the finale. Damon does a good job fitting in with the loose, goofy tone of the films, which, unlike most trilogies, didn’t vary much in quality. [B+/B+/B-]

Gerry” (2002)
Everything concerning “Gerry“‘s existence is inexplicable, from its creation (considering what it followed), its casting (an A-lister in a meditative and minimalist art film?), and its inspiration (the director continued the aesthetic with “Elephant” and the too-derided-by-Cobain-obsessives “Last Days“). But if taken completely on its own terms, the film is a beautiful, mesmerizing and simple tale of two friends who arrogantly stray off the beaten path, paying heavily for it in the end. It’s often aimed at for being pretentious and empty, but it’s a bit more profound than that — any less experienced director would’ve surely had the two spurt overly meaningful dialogue, but Matt Damon and co-star Casey Affleck either spend their time speaking unamusingly about a video game, or without anything to say at all. Maybe it’s not as powerful as other bare meditative flicks or even as strong as its younger siblings, but it’s quite unforgettable, and if one can look at it with not a condescending eye, but with a patient one, they’ll be rewarded with a rather affecting and unique experience. [B+]

The Bourne Identity/Supremacy/Ultimatum” (2002/2004/2007)
It’s hard to imagine now but Matt Damon’s career was not in good shape when the first ‘Bourne’ film came along. Coming off a series of flops, underperformers and oddities (“Gerry,” “Spirit: Stallion of the Cimarron,” “All The Pretty Horses,” “The Legend of Bagger Vance,” etc.), the only real hits Damon had scored since his breakthrough in “Good Will Hunting” were in supporting roles (“Saving Private Ryan” and “Oceans 11”). But cast as Jason Bourne, a special ops amnesiac, Damon was remade as an unlikely action hero. The series, loosely on the novels by Robert Ludlum, began as “Swingers” director Doug Liman’s passion project, but it was Paul Greengrass who came to define the series. By amping up the pace and bringing his own frenetic visual style, Greengrass crafted two arguably superior sequels that received both critical and commercial kudos. The franchise was so influential it even made James Bond feel uncool, until that series was rebooted in the ‘Bourne’ mold, with less emphasis on gadgets and more on a badass Bond. Though the plots are a little thin, these sleek thrillers are the antithesis of most bloated CGI-driven action films. With three films (and counting) and over $500 million dollars in domestic grosses, the series also allowed Damon to continue working with interesting directors like Steven Soderbergh and Terry Gilliam in projects that might not have found financing were it not for ‘Bourne’. [B]

Stuck On You” (2003)
Oddly enough, one of the Farrelly Brothers’s least funny movies is kind of their most affecting. Centered on two conjoined twins with big dreams, the comedy goes to unexpectedly warm places, mining cheap humor from the deformity of their leads, but genuine pathos during a topsy turvy third act. Most of this has to do with the performances: Greg Kinnear is surprisingly engaging as an egocentric extrovert, while Damon finds humor in playing it straight as a humble romantic with serious self-esteem issues. The Farrellys never found themselves again after repeatedly esoteric films about physical and emotional deformities, but this still stands out as a surprisingly touching high point in their career. [B]

The Brothers Grimm” (2005)
The troubled, long-awaited return of Terry Gilliam, this featured the legendary fairy-tale writers (Damon and Heath Ledger) as nomadic charlatans posing as magic handymen/exorcists. The Grimms encounter a bit of genuine magic and are put to the test — and therein lies the comedy. Gilliam has the reins on this surely unwieldy enterprise and try as the man might, you can’t squeeze movie magic from a film that teeters consistently over the dud-in-the-making crevice. It’s especially unfortunate since both Damon and Ledger do solid work with underwritten characters. Ledger delivers a lively performance but he’s relegated to the nervy sidekick role more so than Damon, who clearly endeavors to do something more with his pretty-boy hero — interestingly, the two swapped roles not long before production. By most accounts, Gilliam clashed with The Weinsteins over the making of the film, particularly over the question of a false nose for Damon’s character (Bob McCabe‘s chronicle of the film’s production, “Dreams and Nightmares,” is a must-read) and the haphazard plotting doesn’t do Damon many favors. Still, it’s hard not to feel that the film’s still a more enjoyable, coherent watch than either of Gilliam’s subsequent pictures. [C]

Syriana” (2005)
Stephen Gaghan’s film hasn’t stood up as well as some of its contemporaries, sometimes coming off as a big-screen version of an article in “The Economist,” but for the most part it was a timely and effective ensemble thriller. Here, Gaghan does Damon a huge favor in presenting the actor with Bryan Woodman, a compelling protagonist if there ever was one. After Woodman’s family suffers a tragedy at a private party hosted by an oil-rich emir, the energy analyst finds himself in the favor of progressive Prince Nasir (a fantastic Alexander Siddig). Damon is appropriately torn, faced with exploiting the tragedy and advancing himself astronomically, while his wife Julie (Amanda Peet) suffers in silence. As an American hobnobbing with the Middle East elite, Woodman’s demeanor is one of mixed cynicism and genuine wonderment at a society that has flourished under an oft-unforgiving physical and cultural climate. It’s a complex performance, maybe even simplistic in how it evidences an executive whose intellect is dealt out to the job and the job alone, but the few emotional moments Bryan has are undoubtedly effectively conveyed by Damon. To stand out in a massive cast is worth commending and Damon is up to the challenge. [B]

The Departed” (2006)
While far from Scorsese’s best work, “The Departed” remains a well-crafted, hugely enjoyable pulp crime flick, that certainly improves on its subject matter, the Hong Kong film “Infernal Affairs.” The film’s chock-full of pleasures and Damon’s performance, while not the most immediate, is the one that lingers long afterwards. Simply put, he’s astounding, the best he’s ever been, and looking back now, it’s astonishing that he was overlooked in awards season in favor of co-star Mark Wahlberg. To all appearances the same kind of all-American boy that Damon’s made a specialty of, Colin Sullivan in fact a spineless piece of shit, whose soul has rusted and corroded away over the years. Damon effortlessly portrays the self-loathing and turmoil that comes from living a false life without any of the histrionics of his co-lead, Leonardo DiCaprio. The elevator scene at the end, in which Damon switches on a dime from self-righteous bravado to pathetically pleading to be put out of his misery by his captor, is a masterclass in screen acting. [B+]

The Good Shepherd” (2006)
Written by Eric Roth (“The Insider,” “Munich”) and directed by Robert De Niro, “The Good Shepherd” threw many for being a sober, clinical and incisive look at the emotional toll of espionage work instead of gritty spy thriller and that’s too bad, because the film is definitely underrated and deserves a second chance. Told through the prism of the founding of the CIA, Damon plays Edward Wilson, an agent of the newly founded organization whose work takes him around the world and has him bear witness to operations most Americans could and would never know about. But the film is as much about the machinations of the wheelings and dealings of the spy agency but the personal sacrifice Damon must make as a person and in his relationships (particularly to his wife played by Angelina Jolie). As William Hurt’s character points out, the agents spend their lives looking over their shoulders for “pennies” in compensation. Wilson is forced to choose between his country and his family and the cold realization is that such a choice can’t be made because selecting one means losing the other. De Niro’s film is ambitious in scope, a detailed (some would argue too detailed) history of the CIA along with a stoically depressing personal story. Not an easy watch and it’s certainly clear why critics balked and audiences walked. But Damon here is a revelation, coldly embodying a spy who at work and at home can’t give away the roiling emotion beneath his poker-faced facade. It’s a stirring turn in a film that that was largely misunderstood. [B]

The Informant!” (2009)
Damon has never been funnier than as Mark Whitacre, the delusional whistleblower who broke open a price-fixing scheme at his lysine-producing company, under the illusion that he was a top secret spy. “The Informant!” establishes Whitacre as someone who thinks there are prizes for “being the good guy,” oblivious to the reality around him. Steven Soderbergh’s tone is mostly amused farce, as if the delicate balance of real-world big business and the cartoonish sight of overweight Midwestern rube Whitacre is always threatening to topple. Credit to Damon’s overlooked performance, a wonder of tics and mannerisms of surprising depth, capturing a damaged psyche while keeping him in the realm of believable folksiness. [A-]

Green Zone” (2010)
Drawing most pre-release buzz for being over-budget and over-schedule, and with many merely assuming the film would essentially be a “Jason Bourne Goes To Iraq” tale, the finished product was something a bit smarter than anyone gave it credit for. While it does employ director Paul Greengrass’ shaky-cam technique, the film finds Matt Damon playing Miller, a U.S. Army Officer who begins to realize the weapons of mass destruction that he’s supposedly searching for might all just be smoke and mirrors. His search for the truth (a common theme in Damon movies) finds him mixing with a great array of supporting actors including Amy Ryan, Brendan Gleeson and delightfully slimy Greg Kinnear. Damon is not doing anything particularly challenging or groundbreaking with the part here, but his conviction is palpable and drives the engine of the movie as well as the audience interest to see it play out. If the movie stumbles a little bit, the latter third of the film, with Miller outrunning some pretty cartoonish villains who are chasing him at the behest of Kinnear’s character, strains the otherwise sober tone and cold logic of the rest of the film. But it’s a minor distraction for an Iraq war film that deserved a much better reception than it got. [B]

Hereafter” (2010)
Clint Eastwood’s afterlife melodrama is not without its grace notes, though he flubs the delivery in the final half hour by attempting to resolve the unresolvable. His surprisingly sloppy craft doesn’t distract from some of the best work of Matt Damon’s career. As a clairvoyant who can speak to the dead, Damon is appropriately tortured, but he creates a three-dimensional characterization by filling in the margins with a likable corny sense of humor that plays less as moments of levity than as a defense mechanism used by a fairly damaged person. Amongst the three international stories that make up the narrative of “Hereafter,” it seems a little hokey to say that the one featuring the Big American Superstar is the best, but Damon has simply evolved that much as an actor that his struggles outshine any of the superficial obstacles present in Peter Morgan’s flawed script. [C+]

True Grit” (2010)
It’s not the showiest or even the most nuanced character in the Coen Brothers‘ rapturous “True Grit” remake, but Damon’s dickish Texas Ranger LeBoeuf still manages to be an indelible oddball. Between his typically Texan self-aggrandizing (this writer was born and raised in the state, so this especially rung true), 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. What’s even more amazing is that in early interviews, Damon admitted that his entire shtick was basically an impression of Tommy Lee Jones, which lends it an entire meta-dimensional quality that, if we think about it for too long, might make our heads explode. [A]

Odds & Ends: Obviously, we didn’t have time to fit everything in, but for the completists, there are a handful of major performances that we did miss. Firstly, “School Ties,” in which he played a preppy, anti-semitic villain against a young Brendan Fraser, and acquitted himself well. His first big lead was “The Rainmaker,” a part which his wide-eyed idealism was well-suited for. The film’s not as bad as history suggests — it’s arguably in the top tier of Grisham adaptations, but it certainly marked a black mark in the career of Francis Ford Coppola, who directs entirely anonymously. “All the Pretty Horses,” meanwhile, promised a good deal, but Billy Bob Thornton didn’t have the directorial chops to pull it off, even before a post-production hackjob by Harvey Weinstein. Finally, as fine as he is the film, no one on staff could summon up the energy to sit through the snooze-fest that is “Invictus” again.

Damon also had a supporting role in Walter Hill’s “Geronimo: An American Legend,” and let’s not forget his debut in the early Julia Roberts vehicle “Mystic Pizza.” He’s also cropped up in a number of Kevin Smith’s films: mostly in cameos, although his biggest role for the ‘filmmaker’ (inverted commas deliberate) was as the psychotic angel Loki in “Dogma.” The film’s an unholy mess, but Damon and BFF Ben Affleck are the best things in it not called Alan Rickman. He’s also good value playing himself, shooting “Good Will Hunting 2: Hunting Season” in “Jay & Silent Bob Strike Back.

Damon’s made something of a habit of cameos; some unlikely (the long-forgotten teen sex comedy “Eurotrip”), some just dull (“Finding Forrester”) and some more creditable — Damon pops up both as a good-luck charm in both Coppola’s comeback flick “Youth Without Youth” and Steven Soderbergh’s second part of “Che.” Like most stars, he’s lent his voice to animation a handful of times, although never to great success: Miyazaki’s “Ponyo” is the most respectable, certainly against “Titan A.E.” and “Spirit: Stallion of the Cimarron.”

Finally, Damon’s popped up in TV sitcoms a couple of times, displaying the comic skills he doesn’t always get to play with on the big screen. He camped it up as a would-be chorister in “Will & Grace,” and most recently and far more successfully, killed it as Liz Lemon’s pilot boyfriend Carol Burnett (yes, Carol Burnett…) on “30 Rock.”

Coming up for the actor is further voice work on “Happy Feet 2,” Cameron Crowe‘s “We Bought A Zoo,” the seemingly-eternally delayed “Margaret,” hopefully Steven Soderbergh‘s “Liberace” opposite Michael Douglas, and perhaps most excitingly, teaming with “District 9” helmer Neill Blomkamp on the mysterious sci-fi project “Elysium

Gabe Toro, Katie Walsh, Rodrigo Perez, Kevin Jagernauth, Mark Zhuravsky, Oli Lyttelton, Christopher Bell, Drew Taylor, Cory Everett

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