5. Vaginatown (2008)

In order to distract Hank from his heartbreak, Ashby arranges a sex session with popular, yet incredibly annoying, celebrity chef, Chloe Metz. Charlie takes on a new client who’s eager to land the lead in a porn film called Vaginatown. Charlie meets with the film’s director and secures her the part, but only after investing $100,000 of his own savings.

Release date: 2008-10-26