Vince, Eric, Drama, and Turtle are forced to move out of the mansion. Eric moves in with Sloan and Drama wants to get an expensive condo. With "Medellin" getting into the early stages of pre-production, a surprise cast member is asked to direct.
Drama has an offer from Brett Ratner for Rush Hour 3; Ari finds a backer for Medellin, but the source of his wealth, and his wife's intentions toward Vince, are shady; Turtle has a date with Kelly, but it is under the watchful eye of her father.
Eric and Vince are determined to get Medellin off the ground, but the rights to the script stand in their way. Feeling tense the day of the Five Towns television premiere, Drama seeks relief at a massage parlor, but can't avoid unflattering comments about him in the trade magazine Variety. At an auto-body shop, Turtle meets a girl who shares his love for limited-edition sneakers, but her overbearing father hampers his game. Johnny takes a late night drive to the Grand Canyon.
"Medellin" is back on the table for Vince, but Ari and producer Nick Rubenstein must make the deal happen on the holy day, Yom Kippur, they have until sundown, and must finish the deal without the use of a cell phone; Eric wonders how the relationship between Vince and Amanda is affecting the deal; Drama grows attached to a race horse.
Drama finds out that he will be the target on Pauly Shore's new Punk'd like reality show; Eric tries to relieve the tension between Vince and Amanda; Ari is jealous of a former fraternity brother.
Amanda makes Vince an offer that he cannot refuse; Babs orders Ari to fire an inept employee.
Amanda gets angry when Vince and Eric procrastinate over the Edith Wharton movie; Turtle and Drama find some dream dates at the dog park.
Vince's new agent wants him to do a period film; Eric and Vince agree to have lunch with Ari; Turtle plans Vince's birthday party.
With the apparent loss of the Ramones project and with Ari to blame, Vince and the guys begin to look for other agents to represent him.
Eric, Ari, and Bob pitch the Ramones film project to the studios which causes a power struggle between Ari and Bob. Turtle wants a pair of limited edition shoes which Vince tries to buy for him. Drama begins filming his pilot.
Drama and Turtle go looking for Saigon on the day the record-deal's supposed to be signed. Eric comes up with a project for Vince.
The gang heads to Vegas for a much-needed break and a $100,000 promotional appearance for Vince. But it turns out that Turtle reaps the benefits from the appearance. Eric gets jealous when Seth Green makes insinuating comments about Sloan. Vince and Ari partner at the tables, but Ari loses it when Vince's luck ends. Drama lays it on thick with his masseur, leading to an awkward misunderstanding between them.
Vince and the entourage receive news that "Queens Boulevard" will be receiving a nationwide release. Ari must compromise with a rival to avoid threats from a group of aggressive agents. Drama is nervous about an important audition and begins to take his anger out on everyone.
Eric starts falling for the wrong girl after his threesome. Ari and Terrance come to an agency settlement. Vince is to be auctioned off at Sloan's charity function.
Vince increases his asking price for Aquaman 2, which forces Ari to ask the studio head for yet another favor. But Vince insists that Ari finds Drama a job before he'll accept any offer from the studio. Meanwhile, Eric's girlfriend and her best friend make him an offer he can't refuse, even if there are ground rules.
Vince, Eric, and Ari seek to find a resolution to scheduling conflicts that would prevent Vince from doing both Medellin and Aquaman 2. Turtle deals with Saigon's rising popularity, while Ari deals with his daughter's continued obsession with Max.