Shot as a documentary we join Billy, Eric and Vince arriving in Columbia to film Medellin. Billy falls for one of his actresses and can’t think how to finish the film. Johnny tries to get a part in the film and Turtle tries to stay out of harms way while Ari is filmed back in LA giving his advice on how to make a movie. Eric keeps calm and helps Billy solve his creative problems and gets the movie made on budget.

Back in LA Eric and Vince want to see the first cut of Medellin. Billy says he needs another month to edit and when Eric demands to see it he runs away. Eric finally convinces him to show them the movie which Vince loves but Eric doesn’t. To welcome Vince back to LA, Johnny agrees to host a party at his new apartment. Turtle invites dozens of people and so Johnny goes to great effort to ensure that no one will ruin his new place. Ari and his wife are told that their son might not get into the exclusive school where their daughter goes.

Eric wants Billy to make some cuts to Medellin but he refuses. Eric seeks Ari’s advice and then tries to sell the movie to Harvey Weingard. Vince goes to Dennis Hopper’s house and bets money he doesn’t have on a soccer match. Johnny takes Turtle out to meet a woman he badly wants to sleep with. But when her friend turns out to be old and overweight Turtle wants to leave.

Eric is too scared to tell Harvey that they won’t be selling him Medellin. Johnny wants his condo to be annexed by Beverley Hills and so he befriends the Mayor. The Mayor wants Vince’s help to pick up women. They head to a club but the Mayor ends up with a transvestite. Meanwhile Ari is trying to read an M. Night Shyamalan script on the same night as his wife is trying to celebrate her best friend’s engagement. The valets switch his cars and he ends up spending the night in jail for speeding.

Someone has leaked the Medellin trailer onto Youtube. While the buzz builds and the offers come in for Vince, Billy is angry and thinks Eric leaked it. They get into a fight and then have to put their differences aside for an interview promoting the movie. Meanwhile in order to get Vince the project he wants Ari has to screw over both Dana Gordon and Josh Weinstein. But in doing so he manages to sell the dream team of Vince, Eric and Billy just as Eric vows not to see Billy again after Medellin. Johnny is going back to work and wants to look young. He sees a trucker hat which he thinks will help his look but he can only purchase it from a medical marijuana facility.

Billy apologises to Eric about the leaked trailer. Having done so Eric agrees to work with him on “Lost in the Clouds.” They meet with Dana Gordon and Billy’s behaviour drives Eric to not want to be involved with the movie and advise Vince not to do it either. Meanwhile Lloyd is heartbroken when his boyfriend Tom leaves him. Ari can’t function without Lloyd and so tracks down Tom and lies to him about Lloyd’s cheating. Turtle’s cousin Ronnie is in town with a way to make money off baseball legend Sandy Koufax.

Johnny goads Eric about not being able to have unemotional sex. Vince bets that Eric can get laid before Turtle, and Johnny takes the bet. Vince and Eric meet two British girls by the pool while Turtle meets a girl from the internet who has a furry fetish. Eric runs into Sloan but she has moved on. Meanwhile Ari tries to blackmail Principal Preston but finds him to be incorruptible. Finally he begs him to let his son in to his school and they make a deal.

Eric rents his own office but finds it difficult to be taken seriously because no one knows who he is. Ari has to give Mary J Blige new project ideas and two brothers who work for him threaten to ruin the meeting. Vince tries to buy Eric a new desk but Gary Busey has already bought the one he wants.

The entourage has moved to a new house up in the hills. While trying to find it Eric’s car gets hit by Anna Faris. He ends up giving her career advice and she asks him to become her manager. Turtle heads out shopping and meets some girls to bring home. But on the way he is stopped by the police and told to drop his last bit of weed down the drain. Ari’s wife is asked to reprise her role on The Young and the Restless. Ari doesn’t want her to do it and becomes very jealous when he discovers she has to kiss a Latin heartthrob.

Billy decided not to adapt the book “Lost in the Clouds” and instead presents a new film called Silo to Dana Gordon. She and Ari are furious but Vince likes it so much that he asks Ari to get him this film instead. Eric is up in the hills helping Anna Faris on a photo shoot. Her medalling boyfriend causes problems and he eventually forces her to break up with him. When Eric returns Ari has managed to convince the network president to go with Billy’s new movie instead.

Eric invites Anna out to celebrate the boys leaving for Cannes. Billy likes her and asks her to be in Silo. Eric is caught in a difficult position as both her manager and a producer on the movie. Ultimately his lack of honesty means she fires him. Meanwhile a terrorist threat at LAX causes the airport to close. Ari is busy trying to make things right with his wife and Lloyd who both want to go to Cannes. In the end Kanye West offers the entourage a ride on his private jet.

The entourage and Billy and Ari are at the Cannes film festival. They meet up with Yair Marx at Nicky Rubenstein’s behest and he offers them thirty five million dollars to buy “Medellin.” They turn it down because they don’t believe he has the distribution in place to make a great movie. Ari wheels and deals and gets a good offer from Dana Gordon. But in the meantime Yair offers Nicky seventy five million dollars and buys the movie. At the premiere the audience hate “Medellin” and Yair reneges on his offer. Harvey steps in and offers one dollar for the film which they take. Meanwhile Johnny is confident he can live out his French fantasy because “Viking Quest” was a big hit in France. He meets a girl (Jacqueline) on Yair’s boat but loses her when he kicks up a fuss about his hotel room. He hooks up with her again at the premiere and tells the guys that he is in love with her.