An advertisement promoting Aquaman's box office success appeared in Variety on June 19, 2006, to coincide with episodes from Entourage's third season.The third season continues with the Aquaman plotline as the movie premieres and becomes a huge hit. Problems arise however when Medellin, Vince's dream project about the life of Pablo Escobar, conflicts with the schedule of Aquaman 2. The end result is that Vince is unable to star in either and is fired by Warner Brothers.
Ari meanwhile has to juggle his new, failing, business with keeping Vince happy. Even though Ari manages to set up a successful new agency with the help of Barbara Miller (Beverly D'Angelo), it leads him to neglect his star client.
E's relationship with Sloan comes into question when he has a threesome with her and her friend Tori (Malin Akerman), to whom E is attracted. Tensions rise further when E is confronted with Sloan's stalker Seth Green.
Near the end of the season, Drama finally lands his big break as he's signed on to the new series Five Towns. Turtle's career as a music manager ends unceremoniously when he is bought out by Saigon's original manager. In the season finale, Ari is fired as Vince's agent when his abrasive methods lead to him being unable to secure a film about punk rock band The Ramones.
Third season, part 2
The second part of the third season focuses almost entirely on Vince and Ari and the troubles surrounding Medellin. Attempting to get Vince back, Ari convinces him that he can secure the film after all. Vince's new agent, Amanda (Carla Gugino), tries to steer Vince towards a different film, but he ends up refusing.
To compound their problems, they both admit to a mutual attraction, and have a relationship. When Medellin once again slips Vince's grasp, he questions Amanda's motives. After proving her innocence, she drops him as both client and boyfriend. With the help of Ari, who is once again hired, Vince and E finally secure their dream project when they buy the rights to the film themselves. Billy Walsh is signed on as the director with E given his first shot at producer.
In the continuation of the previous part's subplot, Drama's star rises, and Five Towns becomes a hit. At the end of the season, Vince (along with Turtle), impoverished after buying Medellin, moves in with Drama, the new star. E proceeds to move in with Sloan.