The Talented Mr. Ripley (1999), directed by Anthony Minghella
Though it's set in the 1950s, not the '20s, The Talented Mr. Ripley feels at first like a reincarnation of an F. Scott Fitzgerald novel. Dickie Greenleaf is a Princeton graduate who lives decadently in Italy, surrounded by jazz and supported by his father's money. Tom Ripley is a bit like Jay Gatsby--he can enter this world of wealth only as a spectator or an interloper. But while Fitzgerald built sympathy for his characters' tragic destinies, this film asks us to root for a sociopathic killer's ingenious escape from the consequences of his actions. Nick Carraway had a heart and Gatsby a soul; Tom Ripley has nothing but talent.