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.

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.