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Vince is feeling insecure about more than just his career when former flame Justine Chapin pawns him off on her friend at a party. Eric offers to represent LB and Nick, two writers of an indie film script, but can’t get them Vince, or any help from Ari. Drama maintains constant contact with Jacqueline.
As the dismal reviews for Medellin continue to roll in, Vince hides out in a Mexican paradise with Turtle. Meanwhile, producer Carl Ertz wants a meeting with Vince about a role in a guaranteed hit, and Eric and Ari go all out to persuade him to come back to LA. Drama turns prima donna during a Five Towns photo shoot, and begins a “virtual” romance with Jacqueline, his Cannes girlfriend.
In the fourth-season finale, attempts to sell “Medellin” at Cannes are complicated by the fact that no one has seen the finished product. Meanwhile, the popularity of “Viking Quest” gives Drama a boost.
A security threat at LAX strains everyone’s hopes of getting to Cannes in time for the Medellin premiere. Mrs. Ari and Lloyd both wish to take the trip with Ari to Cannes. Walsh writes Eric’s new client into his script. Help in the end comes from a very unexpected source.
Vince, Ari, and Dana Gordon receive the script for Vince’s next project, but Billy’s interpretation is vastly different than what he was supposed to write. Vince loves the script anyway leading Ari to try and keep the studio interested. Eric is occupied with a new client and her boyfriend.
Eric gets into a fender-bender with Anna Faris, leading to what he believes to be “a little moment,” but in the end, his career is about to change. Ari’s wife acts on a soap opera, leading him to try and dissuade her from doing so. Turtle gets prepped for a party by picking up some provisions, and girls, only to encounter the law on the way home.
When Eric gets his own office, Vince eyes a piece of antique furniture that also has a rich history, but someone has already gotten his hands on it. Ari preps for a meeting with R&B superstar Mary J. Blige, but has to contend with twin-sibling rivalry in his own office.
Eric and Turtle’s love lives become a source of amusement for Vince and Drama. Ari adjusts to having his son in public school.
Billy makes amends with Eric over the online leak of Medellin. Lloyd takes a leave of absence from the Miller Gold Agency for personal problems. In the meantime Turtle makes an investment.
The Medellin trailer is leaked on YouTube and Billy blames Eric. Drama joins an exclusive medical marijuana club. And Ari and Lloyd engage in sabotage so that Vince can get his next project.
Ari mistakenly mishandles a top-secret script, a mistake that lands him in jail. Drama fetes the mayor of Beverly Hills, with help from Vince. Eric has to go back on his word with Harvey Weingard, a Hollywood heavyweight, when Medellín is accepted into the Cannes Film Festival.
Billy submits Medellin to the Cannes film festival, leading Eric – who thinks the film needs work – to worry that it will get rejected. Drama rekindles an old flame, and brings Turtle in as his wingman. Vince gets in over his head in Malibu.
With the gang arriving back in America, Drama plans a party for Vince at his new condo. Ari learns that his son might not be accepted to an exclusive private school. Billy’s insecurities may prevent Vince and Eric from seeing the first cut of Medellín.
A behind-the-scenes documentary about the filming of Medellín in Bogota, Colombia. Billy and Eric clash on the set about keeping the film on track. Billy becomes attracted to an actress which ends up disrupting the production. Drama tries to get Billy to give him a part in the film.
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, 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” premiere, Drama seeks relief at a massage parlor, but can’t avoid Daily Variety. At the auto-body shop, Turtle meets a girl who shares his love for limited-edition sneakers, but her overbearing father hampers his game.
“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 with 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 and Ari is jealous of a former fraternity brother.
Amanda needs an answer on the period film, but Vince won’t commit to any other project until the cameras are actually rolling on ‘Medellin.’ Amanda persists, so Vince has the crew read the script to get everybody’s opinion. Unfortunately, the script is so dry that nobody can get through it, leading Vince to realize that the project isn’t right for him after all.
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. In the meantime Eric and Vince agree to have lunch with Ari and 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. Ari, hearing of Vince’s shopping, fights with all his might to get back the movie. While looking at other agents, Vince realizes they are just too corporate for him and the “scumbag” Ari is the best in the business. However, since Ari cannot get the movie back, he tries to win Vince back with a corporate-style presentation himself. This backfires because the boys find Ari to be just like everyone else now and fire Ari as they walk out of his office.
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.
Dom, who has now become a part of Vince’s posse, ends up telling Vince a story that helps him get his dream role in the film, Medellin.
The gang have no idea what to think when Vince decides to hang out with his old friend who happens to be an ex-con and wants them all to be friends. Meanwhile, Ari’s daughter ends up becoming friends with an up and coming movie star.
Ari and Eric are worried because rolling blackouts have hit Los Angeles and it may cause a decrease in the box-office totals for “Aquaman” in the area. The two ponder how to keep Vince from finding out the situation.
As the gang anticipates the upcoming premiere for “Aquaman”, the search is on for a perfect date for Vince. Meanwhile, Ari tries to cope with financial difficulties and his new office space, which is not quite what he is used to.
Vince’s despondent mood forces Eric to consider fending for himself. Meanwhile, Ari has meetings at a coffee shop and Drama and Turtle make a vow of silence.
Vince is blinded by love, and Eric gets cozy with Sloan. Meanwhile, Ari gets shot down in the war room, and Drama and Turtle use their paparazzi skills on an important spy mission.
When Vince and his co-star act out of character, Ari and Eric must face a team of angry handlers – and each other. Meanwhile, Drama and Turtle make a musical discovery while retrieving a stolen car.
Vince receives courting lessons from Terrance and a valuable gift from Ari, Shauna flips over a press leak, and Eric gets attention – and ammo – from Terrance’s daughter Sloan. Meanwhile, Drama grows overexcited about a co-star, and Turtle plays ambassador for Vince.
Vince gets up-front about his feelings for Aquagirl, sending everyone into a panic. Meanwhile, Ari’s partner Terrance resurfaces, Eric splurges on an ‘investment’ suit, and Drama and Turtle have high hopes for Little Miss Ari’s Bat Mitzvah.
Vince makes a splash at a convention with his new co-star. When neither Eric nor Shauna can appease a bitter journalist, Turtle sends a pair of professionals to the rescue. Ari gives Drama a rockin’ birthday gift.