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His smile can light up the screen, but he keeps that in reserve. Approaching the age of 40, Matt Damon still looks as fresh-faced as he did when he first drew wide attention for his supporting role in Edward Zwick’s Courage Under Fire](Courage Under Fire (1996) - Movie | Moviefone), released in 1996. He conveyed great admiration for a certain character, even while suggesting a layer of doubt that hid below the surface. It was a fine role, but it wasn’t his best.
He made a big splash the following year as a young lawyer in Francis Coppola’s adaptation of John Grisham’s The Rainmaker](The Rainmaker (1997) - Movie | Moviefone), and as a genius with issues in Gus Van Sant’s Good Will Hunting](Good Will Hunting (1998) - Movie | Moviefone). The latter, based on a script that he wrote with his good pal Ben Affleck, provided him with a showcase dreamed of by all actors, and earned him an Academy Award nomination. (He and Affleck won, instead, for their screenplay.) The two parts established him as a leading man – he demonstrated confidence, charm, and a measure of vulnerability – but they weren’t his best roles.
He teamed with Ed Norton in John Dahl’s Rounders](Rounders (1998) - Movie | Moviefone), and was overshadowed in the process, before taking a major stride forward with Anthony Minghella’s The Talented Mr. Ripley](The Talented Mr. Ripley (1999) - Movie | Moviefone). Damon came very close to capturing the elusive essence of the titular character, created by Patricia Highsmith, leaving behind the trail of a haunted, demented man. Damon was very, very good, and it was his best role up to that date. But he’s done better since then.