Entourage: All of the Movies Vincent Chase Has Starred in

Though Smoke Jumpers ended up on the cutting room floor, Gus Van Sant saw some footage and was impressed with Vince's work. He then put Vince in the big-screen adaptation of The Great Gatsby he was producing, with Martin Scorsese as director. Vince played Nick Carraway, while Leonardo DiCaprio played Jay Gatsby and Natalie Portman played Daisy Buchanan. Keep in mind that this was years before Leo actually starred as Gatsby in real life.