7. 'The Talented Mr. Ripley'
Matt Damon's late 1990s winning streak continued with The Talented Mr. Ripley. He portrayed a New York City grifter in the 1950s that gets mixed in the drama of a rich family. He travels to Europe and tries to convince the playboy son to return to America, but he winds up killing him in a fit of rage. Things only get more complicated from there, but it's a stellar thriller that grossed $130 million and won rave reviews.