The Talented Mr. Ripley (1999)

In late 1950s New York, a young underachiever named Tom Ripley is sent to Italy to retrieve Dickie Greenleaf, a rich and spoiled millionaire playboy. But when the errand fails, Ripley takes extreme measures. Starring Matt Damon, Gwyneth Paltrow, Jude Law! (2hr 19m)