“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 Weinsteinsover 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 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-]