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]