The Talented Mr. Ripley (1999)

Conman Tom Ripley convinces ship magnate Herbert Greenleaf he went to an Ivy league school with his son, Dickie. Greenleaf asks Ripley to convince his son to come home. Starring Matt Damon and Jude Law and based on the first novel in Patricia Highsmiths Ripliad, Damon wasnt the only actor to play Ripley. Alain Delon, John Malkovich & Andrew Scott have all played the American conman.