9 Milestones in the Evolution of Matt Damon

Will & Grace (2002)

Shades of what would come when Damon would expand his sitcom resume with 30 Rock, but his appearance on Will & Grace was one of the first signs that Damon was a guy who was up for anything as long as he thought the role was fun.

Eurotrip (2004)

Is this a calculated move that was conceived somewhere in a back room by a group of publicists? Probably. But that doesn't mean it didn't work. The last movie one would ever expect to see Damon would be in this little seen 2004 romp about four students making their way through Europe, but, alas... there he is, playing the lead singer of a rock band who also happens to be involved in sexual relations with the main character's (Scotty) girlfriend. A precursor to the "I'm F*cking Matt Damon" Sarah Silverman video.

The Bourne Supremacy (2004)

Aside from being the first of the Bourne movies to feature Paul Greengrass as the director, what makes Supremacy a milestone above the other two is how it marks Damon's commitment to being a bona-fide action star. It's also his first sequel in general, making him an official franchise guy (his second, Oceans 12, would be released later in 2004).

30 Rock (2010)

Again, no one likely expected Matt Damon to play a recurring role on an NBC comedy -- even one as well-regarded as 30 Rock -- let alone be so good in the role or eventually appear in the series' live episode. But that's the thing about Damon: Other than Good Will Hunting and the Bourne movies, his box-office track record isn't the best for movies where he's the main draw. What keeps Damon relevant is his "up for anything" persona: His most recent film, Hereafter, was a bomb critically and commercially, but Damon himself never took a hit because of the long tail of goodwill following gambits like 30 Rock.

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