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+]