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]