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.