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“Saving Private Ryan” (1998)
It’s not the biggest role, but it is the title role. Damon plays the titular Private Ryan who Tom Hanks and his crew are looking for. Steven Spielberg’s World War II epic is considered one of the best war movies ever. While Damon may not be involved in the big D-Day invasion scene, he definitely makes his mark on the film.
“The Talented Mr. Ripley” (1999)
Damon didn’t exactly make his name playing saints, but Thomas Ripley takes things to a new level. He’s a sociopathic social climber and a pathological liar. While Dickie Greenleaf may have been a rich jerk himself, it’s hard not to feel bad for him once Tom takes an interest in him.
