Based on the HBO Comedy series. Movie star Vincent Chase (Adrian Grenier), together with his boys, Eric (Kevin Connolly), Turtle (Jerry Ferrara) and Johnny (Kevin Dillon), are back…and back in business with super-agent-turned-studio head Ari Gold (Jeremy Piven). Some of their ambitions have changed, but the bond between them remains strong as they navigate the capricious and often cutthroat world of Hollywood.
Ari, now fending off a Cannes-envious Lloyd in addition to talking his wife down from a punitive spending spree, arrives late to the Hollywood rush for private jets after LAX closes. Desperate to fly his guys to Cannes, Ari calls Sydney Pollack and manages to pack five of the six onto the filmmaker’s plane. E, on the other hand, gets shot down when he finally admits to Anna that – in addition to having a crush on her – he thinks she should pass on ‘Silo.’ In light of his conflicting interests, the actress sends E packing, but when he gets to the Van Nuys airport, it turns out Ari’s math skills don’t measure up. Even without Lloyd and Mrs. Ari, the guys tip the scales past what Pollack’s pilot will allow. Vince decides it’s all or nothing and passes on the flight. As the group turns to leave the terminal, Kanye West and his entourage roll up, granting the LAX refugees seats on his 727. From the tarmac, Ari calls his wife, apologizing for leaving her behind and explaining that he just wanted to have a guys-only adventure. Mrs. Ari, surrounded by a room full of designer purchases, forgives him and tells him to enjoy his trip with the boys. Voila!
Ari’s search for a ‘Medellin’ buyer gets off to a strong start. A few key deceptions – appearing at a party with Harvey Weingard and spreading disinformation through Lloyd’s network of gay assistants – bait Dana Gordon into making an offer, but it falls short of Yair’s sum. Vince and E level with her in hopes of landing a legitimate studio, offering to leave their money on the hook if she can cover Nicky’s investment. The deal lasts for about five minutes, until Yair catches wind of it and offers $75 million directly to Nicky. Unable to argue with cash like that, Vince and company are all smiles as they follow the red carpet into their premiere. When Drama hears Jacqueline scream from the crowd, he scoops her up and carries her off to the beach to consummate their relationship on the sand. Vince doesn’t get so lucky with the screening of ‘Medellin.’ The crowd’s boos at the end of the film give way to a diatribe by Walsh, and Yair immediately backs out of the deal. With nowhere left to turn, Ari accepts a backhanded offer of one dollar from Harvey Weingard, banking on the studio head’s financial savvy to dig them out of the hole.
Ari’s newest client, Walsh, also causes headaches when he turns in a script for ‘Lost in the Clouds’ without running it by the agent. It doesn’t help that Walsh has renamed the film ‘Silo’ and written a blanket departure from the book. Dana Gordon makes it through 12 pages before demanding Ari pull his client into line. Walsh, of course, refuses to cooperate and fires Ari before the agent can dump him. Unable to catch E on his cell, Ari calls Vince for help, but when the actor peruses ‘Silo’ he discovers its brilliance. In a risky game of hardball, Ari walks the script in to Dana’s boss and tells him he can either produce this ready-made summer hit or explain to his investors how ‘Lost in the Clouds’ collapsed into a debacle. Ari doesn’t earn any friends with the power play, but ‘Silo’ receives a green light. Back at Anna’s shoot Dave returns in a fury, openly accusing E of trying to steal his girl. Finally fed up, Anna breaks up with Dave on the spot, sending him away before finishing her work. E returns home from the set to find Ari, Walsh and the boys toasting to the new project. Cluelessly flipping through the ‘Silo’ script, he asks the guys, "Where’s the snow?"
At the Gold house, Ari’s spotlighting a few flaws doesn’t go over so well. A producer from ‘The Young and the Restless’ calls to ask Mrs. Ari to reprise her role as Kendall Scott, and Ari tries to dissuade her by warning, "You left the show when you were 25, and they shoot in High Def now." Karma comes back around to bite him, though, when he learns his wife will be making out with a hot young Latino named Javier on the show. Ari bribes the young actor with a future in film, but when Javier shies away from kissing Mrs. Ari, she seizes him in a lip-lock. Later, she explains to Ari that all she really wanted was for him to think she’s still sexy. "You’re the beautiful mother of my children," he tells her as he throws her on the bed.
E thinks he’s en route to some star-studded romance himself when Anna calls to set a dinner date. He meets her, but it turns out she already has a boyfriend and wants to hire E as her manager. When E gets back to the house, Drama taunts him for thinking he had a shot with a celebrity, and all Vince can say is, "She wants you to be her manager? Interesting…"