Season five sees Vince returning to California ready to work after spending months relaxing in Mexico with Turtle following the negative backlash from Medellin which has gone straight-to-DVD. E receives a script from a pair of unknown screenwriters trying to get a break in Hollywood called Nine Brave Souls, in which E sees potential. E gets Edward Norton and Amanda Daniels interested, and they change the name of the film to Smoke Jumpers. Ari is determined to get Vince the lead on Smoke Jumpers and after being offered position of Studio Head manages to manipulate the situation (in usual Ari style) and instead gets Dana Gordon the job and uses this leverage to secure Smoke Jumpers for Vince. Smoke Jumpers begins filming, but after several conflicts between Vince and director Verner Vollstedt, Vince is fired from the project. The boys return to New York City, where Vince pursues a role in Gus Van Sant's new film. Van Sant decides Vince is not for his current film, but would love to work with him in the future. After discovering Van Sant said no, Vince becomes upset and fires E, believing that E had made him look desperate. However Vince later apologises when he learns that Es persistence has led to an offer by Martin Scorsese for a lead in his next feature; a re-envisioning of The Great Gatsby set in the Upper WestSide of New York City.
