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Vince, Eric, Drama, and Turtle begin living it up in the wake of Vince's latest hit, while the boys clash with Ari, attend a slew of wild parties, and decide on Vince's next starring role: an independent film set in Queens and directed by a loose cannon named Billy Walsh.
Basking in the adulation from his latest movie premiere, Hollywood 'it' actor Vince Chase joins childhood pals Eric, Drama and Turtle to debate the pros and cons of attending their tenth high-school reunion back east. Meanwhile, Eric – Vince's de facto manager – incurs the wrath of Vince's agent Ari by advising Vince to pass on a script he hasn't even read. On the domestic-security front, Turtle agrees to test the mettle of the entourage's new guard dog, a Rottweiler named Ahnold.
Ignoring the cautionary portents of a negative review, Vince ramps up his already-excessive spending by leasing a new Rolls-Royce. Ari urges Vince to get a "real" manager, causing a wounded Eric to do some soul-searching. Meanwhile, Drama skips a "Vagina Monologues" rehearsal (go figure) to join Vince and the entourage at a wild party hosted by a sexy actress.
After meeting a talk-show host at a boxing after-party in L.A., Vince agrees to appear on his show – despite a long-standing rift between the host and Drama. Eric and Kristen share a long goodbye; Ari puts the full-court press on a famous comic; and Luke Wilson tells Turtle how to score a free home-theater system for Vince.
Vince decides to celebrate the opening night of his latest movie, 'Head On,' with a group date – to Eric's chagrin. Drama's pumped-up gal pal Tanya struts her stuff at a bowling alley; Turtle taps into Vince's fan mail for some action; and Vince turns on the charm with unsullied pop vixen Justine Chaplin.
Vince's fling with a 'cruelty-free' vegan named Fiona – and her friendship with a laid-back L.A. 'sherpa' – brings unexpected karma to the entourage. Eric pushes a promising new script set in Queens; Drama fears the disruptive power of his friends' new relationships; and Turtle barters boots for booty.
Ari's former assistant Josh, now a competing agent, woos Vince and the boys at a wild Malibu beach party. Drama ponders an alternate career in the food-service industry; Eric puts Emily in a compromising position; and Turtle irritates an actor at an art opening.
Eric is concerned over the choice of director, an indie loose cannon named Billy Walsh, for Vince's new film. Meanwhile, Drama lobbies for a supporting role, while Ari finds he can't mix business with pleasure.
Sick of being known as 'Vince's guy,' Eric wants a title commensurate with his responsibilities. With his latest shoot taking him to New York for three months, Vince prepares to say goodbye to L.A. – as well as his many 'special' girlfriends. Meanwhile, Drama debates taking either a high-paying TV role or a low-paying film gig, and Turtle stakes out a claim as Vince's 'farewell party' promoter.
