The first season focuses on Vince’s adventures, as he starts to climb the celebrity ladder following his successful movie “Head On.” Ari and E are working to decide what’s next for the young movie star, but they don’t have similar views on what to go after, so conflict is sure to arise. Halfway through the season, we find out that Vince’s next project will be indie flick Queens Boulevard, much to E’s dismay. The two buddies get into an argument, but they decide to set aside their difference as they leave for New York at the end of the season, to start filming. This is also when E becomes Vince’s official manager.
Elsewhere, subplots include Drama’s struggle to get his acting career back on track and Turtle’s marijuana obsession. The characters’ romantic lives are also showcased heavily – while Vince has many girlfriends, E is dating Ari’s assistant, Emily.
In the series’ second installment, Vince is offered the role of Aquaman, and he convinces the director that he’s the perfect man for the part. However, trouble occurs when Mandy Moore is cast in the leading lady role – Vince’s ex-girlfriend, for whom he still has some strong residual feelings. She’s engaged to be married, but her reunion with Vince is enough to call the engagement off. The two resume their romance, but Mandy eventually returns to her former fiancé, leaving Vince devastated again. Luckily, he finds the power to go one with the movie, despite the awkwardness.
In other news, Turtle becomes a music manager, and Drama is still struggling with his career. Ari has problems as well, in the form of his boss, Terrance McQuewick. Their conflict escalaed and Ari ends up being fired from the agency. E begins to date Sloan, McQuewick’s daughter.
Aquaman premieres and becomes a huge success; so much that Aquaman 2 becomes a no-brainer. However, Vince has his eyes set on Medellin, a project about the life of Pablo Escobar, but whose schedule conflicts with that of Aquaman 2. In a twist, Vince is fired by Warner Bros, and misses his chance to star in either one of the movies.
Meanwhile, Drama has his big break, singing on to the new TV series Five Towns. Turtle’s career as a music manager ends abruptly. E’s relationship with Sloan becomes kind of rocky after a threesome. Ari starts his own business, but the pressure he’s under causes him to neglect Vince, which leads to tension between the two. Vince fires him.
The second part of the season focuses on Vince and Ari’s struggles with Medellin. Ari tries to secure the part for Vince to get his client back, while Vince’s new agent, Amanda, unsuccessfully tries to steer him towards a different project. In the end, Vince hires Ari back, and the two manage to buy the rights for Medellin themselves, with E’s help. Billy Walsh sings on as director.
Elsewhere, Drama’s show is a success, and E moves in with Sloan.
Production of Medellin begins, not without setbacks. Conflicts quickly arise, especially between E and the director, Walsh. E also wants to expand his horizons and ends up representing Anna Faris, but his loyalty to Vince comes in the way and he’s eventually fired. Ari has a lot of personal issues this season, while Drama and Turtle are doing the usual – they procure marijuana, have a good time, engage is suspicious bets. Overall, they’re pretty busy.
At the end of the season, the entourage travel to Cannes, to promote Medellin and, hopefully, sing a distribution deal. Their luck just ran out though – the movie bombs and the team is forced to accept an offer from producer Harvey Weingard of a mere one dollar for the film.
Medellin goes straight to DVD and is consistently referred to as one of the worst movies of the year. Vince returns to California after a few months relaxing in Mexico, and is ready to work again. Eric receives a script with a lot of potential, from a pair of unknown writers. When Ari reads the script for Smoke Jumpers, he convinces E to start a bidding war for the film. Unfortunately though, Alan Gray, the man who fired Vince from the sequel to Aquaman, outbids them.
Ari challenges Alan to a game of golf, eager to get Vince the role he desires. The two get in a heated argument and Alan drops dead. At the funeral, Ari is offered a position as president of a studio, but decides to turn it down and secure Smoke Jumpers for Vince instead. The movie begins filming, but conflict arises once again. Vince is fired by the director, and the boys return to New York. Here, Vince pursues a role in Gus Van Sant’s new flick, but the director politely declines, mentioning that he would love to work with Vince in the future. Frustrated, Vince fires E, convinced that he’s the one who sabotaged him. He later apologizes after he finds out that E’s persistence led to an offer from Martin Scorsese for a lead in his next future. The boys head back to Hollywood.
Elsewhere, Drama keeps working on Five Towns, but his long-distance relationship breaks off, which leads to him braking down during a guest appearance on The View. Turtle starts to date Jamie-Lynn Sigler.
This season focused mostly on individual storylines. Vince is back to A-list status after the success of the Scorsese project, and he’s preparing for his next role, in an Enzo Ferrari biopic. He spends most of the season relaxing.
E moves out from Sloan’s, but he still pines for her. He disbands his company and goes to work for veteran manager Murray Berenson, where he incurs the wrath of one of his colleagues, Scott Lanvin.
Turtle starts college, but his relationship with Jamie-Lynn Sigler doesn’t last that long. Drama leaves Five Towns, but receives an offer to star in his own television show, pending studio approval. Ari is approached by his old boss, Terrance McQuewick, who wants him to buy out his agency. He accepts and finally promotes his assistant, Lloyd, as agent.
At the end of the season, E proposes to Sloan, while the rest of the entourage travels to Rome, where Vince is scheduled to start filming.
While filming an action movie, Vince performs a dangerous stunt, which pushes him to seek out new thrills – including purchasing Vicodin and dating porn star Sasha Grey. The relationship between E and Scott becomes a bit better, as they work together to secure a new project for Vince, Air-Walker. However, when E finds out that Scott possibly supplied Vince with cocaine at a party, things go sour again.
Vince’s drug problems continue to escalade as he starts to work on Air-Walker. His relationship with Sasha is also on the fence after she decides to star in an upcoming porn film. She breaks up with him, and the guys attempt to stage an intervention, unsuccessfully. Vince goes to spend the night at a hotel, where he clashes with Eminem and gets beaten up by him and his security guys. He’s taken to the hospital, where the police find a bag of cocaine in his sweater.
Meanwhile, Turle starts a tequila business, Ari’s life goes down the drain, and Drama gets to star in his own cartoon show, Johnny’s Bananas.
In season eight, Vince is sober after spending a few months in rehab. He’s ready to work and he pitches a movie idea about miners to his buddies, writes the script, and tries to find a way to produce it. He starts to date Sophia, a journalist. Eric and Sloan are no longer seeing each other. She tells E she’s going to leave for New York. He later finds out she’s also carrying her child, but this doesn’t seem to impact her decision to move away. Johnny’s Bananas is pretty successful, and Ari is trying to get back together with his wife. Turtle has some trouble with the tequila business, but eventually becomes very rich, with a bit of help from Vince.
In the last episode, Vince tells the gang that he’s flying to Paris to marry Sophia. E quits his job and decides to move to New York to be with Sloan and their baby. She’s on the fence, but eventually agrees after Vince gives her a speech about how wonderful E is. Ari quits his job for his family and reconciles with his wife. However, in the post-credits scene, he receives an interesting offer to become chairman and CEO of Time Warner. The final scene of the series shows him contemplating the news.