Entourage (2004-2011) Season 5 - 12 Episodes (2008) Buy Entourage Season 5 on Amazon Watch Entourage on Amazon - Free HBO 30-day Trial to Prime Members  Movie star Vince Chase navigates the road to stardom with his agent and group of friends. Season five has Vince trying to overcome the disaster that was Medellin. In Hollywood one good movie makes you a star, and one bad one makes you a pariah.