Entourage Plot Summaries

Plot synopsis

First season
The first season of Entourage chronicles Vincent Chase’s adventures as he climbs the celebrity ladder after his first successful movie: Head On. At the forefront of the first few episodes is the conflict between Vince’s best friend "E" and his agent Ari, who are both working to get the best for Vince, but often differ on how to accomplish this.
Vince’s next project is decided halfway through the season: Queens Boulevard. Signed on is indie director Billy Walsh, who comes into immediate conflict with E. Eventually their differences are put aside and the season ends with the start of production on Queens Boulevard, with E formally becoming Vince’s manager.
Running subplots include: Turtle’s laziness and quest for marijuana; Drama’s attempt to follow in his younger brother’s footsteps; E dating Ari’s assistant Emily (Samaire Armstrong); and Vince’s many and varied girlfriends.

Second season
The second season focuses on Vince’s proposed role in the movie adaptation of Aquaman as the eponymous hero. Ari’s inability to close the contract leads to trouble, but Vince manages to convince the film’s director, James Cameron, that he is right for the part. However, new problems arise when the role of the leading lady goes to Mandy Moore, Vince’s ex-girlfriend, for whom he still has feelings, but who is engaged to be married.
Mandy and Vince resume their romance after Mandy’s engagement shows signs of problems, but she eventually returns to her boyfriend. Initially devastated, Vince finds the will to go on with the movie in the end.
However, Ari has his own problems in the form of his boss and partner, Terrance McQuewick (Malcolm McDowell), who is trying to steal Vince away from him. Near the end of the season, their conflict reaches a head and Ari is fired from the agency. E, meanwhile, starts to date Sloan (Emmanuelle Chriqui), McQuewick’s daughter.
Meanwhile, Drama continues to try to become a star, even considering getting his calves augmented. He is eventually dropped by his agent, Adam Davies, after Vince decides to stick with Ari after Ari is fired. Turtle starts a career of his own, as manager of rapper Saigon.

Third season part 1
The third season continues with the Aquaman plotline as the movie premieres and becomes a huge hit. Problems arise however when Medellin, Vince’s dream project about the life of Pablo Escobar, conflicts with the schedule of Aquaman 2. The end result is that Vince is unable to star in either and is fired by Warner Bros..
Ari meanwhile has to juggle his new, failing, business with keeping Vince happy. Even though Ari manages to set up a successful new agency with the help of Barbara Miller (Beverly D’Angelo), it leads him to neglect his star client.
E’s relationship with Sloan comes into question when he has a threesome with her and her friend Tori (Malin Akerman), to whom E is attracted. Tensions rise further when E is confronted with Sloan’s stalker Seth Green.
Near the end of the season, Drama finally lands his big break as he’s signed on to the new series Five Towns. Turtle’s career as a music manager ends unceremoniously when he is bought out by Saigon’s original manager. In the season finale, Ari is fired as Vince’s agent when his abrasive methods lead to him being unable to secure a film about punk rock band The Ramones.

Third season part 2
The second part of the third season focuses almost entirely on Vince and Ari and the troubles surrounding Medellin. Attempting to get Vince back, Ari convinces him that he can secure the film after all. Vince’s new agent, Amanda (Carla Gugino), tries to steer Vince towards a different film, but he ends up refusing.
To compound their problems, Vince and Amanda both admit to a mutual attraction, and have a relationship. When Medellin once again slips Vince’s grasp, he questions Amanda’s motives. After proving her innocence, she drops him as both client and boyfriend. With the help of Ari, who is once again hired, Vince and E finally secure their dream project when they buy the rights to the film themselves. Billy Walsh is signed on as the director with E given his first shot at producer.
In the continuation of the previous part’s subplot, Drama’s star rises, and Five Towns becomes a hit. E moves in with Sloan.

Fourth season
The fourth season continues the Medellin plotline as production of the film finally begins. Conflicts quickly arise when E admits to being dissatisfied with the first cut after Walsh reluctantly agrees to a midnight screening. Vince and E subsequently clash over the creative direction and financing of the film in an arc which escalates through the season. There is much contention over the ending of the script, and Stephen Gaghan is brought in briefly, at which point Walsh comes up with what he believes to be a good ending.
When the Medellin trailer leaks to the public via YouTube, an opportunity is presented to leverage the resultant hype to broker a deal attaching Vince to a new big-budget project. The deal, however, is unexpectedly sold on the strength of not just Vince, but the "Medellin Dream Team" - also involving E as producer and Walsh as director - at the point when animosity between E and Walsh begins to come to a head. Consequently, E must decide between jeopardizing the deal, and the prospect of working on another project with Walsh, which he had previously sworn he would never do again.
Meanwhile, Ari contends with various complications in his personal and professional lives, including the incapacitating relationship troubles of his indispensable assistant, Lloyd, the uncertainty of his son’s acceptance into the exclusive private school his daughter attends, and interpersonal conflicts between employees of his agency.
E navigates unfamiliar waters as he clumsily attempts to expand the representation of his fledgling management agency beyond Vince, his only client at the time. By chance he comes to meet and subsequently represent Anna Faris, but when his loyalty to Vince and his personal feelings for Faris are set at odds with one another and compromise his professional judgement, he is ultimately fired by Faris.
Drama and Turtle are featured throughout the season in various subplots that see them engaging in the type of antics typical of their characters, such as procuring marijuana and engaging in furry fetishes via Craigslist on a bet.
In the season finale, the entourage travel to Cannes to promote Medellin, and sign a distribution deal. However, the film bombs with the Cannes audience, and they are forced to accept an offer from producer Harvey Weingard (whom they earlier rebuffed) of a mere one dollar for the movie.

Fifth season
The show’s fifth season begins with Vince and Turtle on a beach in Mexico, while Eric and Ari try to get Vince an opportunity to get his career back on track back in California. Medellin has gone straight-to-DVD, and made numerous worst-of-the-year lists, with Vince’s performance coming under fire from critics as well. Drama is also in Hollywood, continuing production of his show Five Towns while maintaining a long-distance relationship with his French girlfriend Jacqueline. Ari and E remain unsuccessful in convincing Vince to return to the States until Ari gets a sit-down for Vince with producer Carl Ertz about a new movie titled "Danger Beach". When Vince and Turtle return, they all realize that Ertz was not actually interested in Vince but was instead using him to secure Emile Hirsch for the role. Seemingly at a dead end, Vince returns to basics and begins reading scripts Ari claims are already taken. One, named Nine Brave Souls, sticks out to Eric. Meanwhile Drama’s nervousness about Jacqueline possibly cheating on him leads to their break-up and he works himself through a guilty frenzy that reaches its peak when he breaks down during a guest appearance on The View. Eric sees potential in Nine Brave Souls and approaches the writers to begin representing them. He gets Ed Norton and Amanda Daniels (Carla Gugino) interested, and they change the name of the movie to Smoke Jumpers. When Ari finally reads the script of Smoke Jumpers he convinces Eric to start a bidding war for the movie with Vince attached. Amanda refuses to participate and passes on it until later reconsidering and making an offer. However, Alan Gray, the man who fired Vince from the sequel to Aquaman, outbids them.
Ari asks for the second lead in Smoke Jumpers for Vince but Alan Gray says no. Vince is offered a role in a new "Benji" movie but after considering it he realizes that Smoke Jumpers is still the movie he really wants. Ari, determined to get Vince the role he desires, challenged Alan to a round of golf for the part. Alan brings PGA Tour pro Phil Mickelson along as a coach and beats Ari. Venting his anger, Alan begins to yell at Ari for even bringing up Smoke Jumpers, knowing he hates Vince; but suddenly drops dead of a heart attack. At Alan’s funeral, Ari takes the opportunity to ask John Ellis, Alan’s boss, about giving the role to Vince. Ellis instead offers him Alan’s position as president of the studio, with Amanda Daniels (Carla Gugino) as the number-two choice for the job. Rather than accepting the offer and abandoning his clients, Ari instead gets Dana Gordon the job, therefore locking up Smoke Jumpers for Vince. Meanwhile, Turtle meets Jamie-Lynn Sigler on an airplane and the two hit it off, but their potential relationship is ruined when Turtle tells the guys she gave him a handjob and they tell everyone. It was revealed to be true.
Smoke Jumpers begins filming and Vince becomes increasingly angry when his co-star, Jason Patric, steals several of his lines. He discovers that the director, Verner (Stellan SkarsgÃ¥rd), gave his lines to Patric. Vince talks to Verner about his frustration over how few of lines he’s been given, and rather than giving him more, he tells Vince about his bad acting habits. Ari signs his old colleague Andrew Klein (Gary Cole) as a new partner in MGA.
Verner eventually fires Vince from Smoke Jumpers when one scene is shot several times without good results and Vince gets angry. Ari flies in but cannot convince Verner to give Vince another chance, so he seeks Gordon’s intervention. She scolds Verner but he storms into a conference room where Ellis is in a board meeting. Furious, Ellis pulls the plug on the whole movie. Meanwhile, Jamie-Lynn forgives Turtle for opening his mouth and appears to want to start a relationship with him if he keeps quiet, so they spend the day together and consider spending the weekend together. However, their plans are cut short when he receives a call from Vince explaining the situation and they all fly back to Queens for a week.
With Vince’s future in acting looking dim, his relationship with Eric is tested when Vince pursues a role in Gus Van Sant’s new film. Eric persistently tracks down Gus in an attempt to convince him to meet with Vince, despite Ari’s opposition. Gus refuses, saying he has seen all of Vince’s work and he is not a fan, but agrees to see the Smoke Jumpers footage. Meanwhile, Jamie-Lynn reveals her relationship with Turtle to the guys. Gus calls back saying he loves the footage and claims that he would love to work with Vince, but not on his current project. Vince becomes upset and fires Eric, believing that Eric had made Vince look desperate. A heartbroken Eric returns to Hollywood to concentrate on another one of his clients, a young and rising comedian named Charlie. Vince later apologizes after learning that Eric’s persistence led to an offer by Martin Scorsese for a lead in his next feature, a re-envisioning of The Great Gatsby set in the Upper West Side of New York City. The episode ends with them all back in Hollywood on their way to celebrate. The final episode also includes a cameo appearance by Michael Phelps.
Sixth season
The season begins with Vince getting his driver’s license, by bribing the driving instructor. Vince is preparing for his new role as Enzo Ferrari in an upcoming movie. Vince and the boys attend the premiere of his film Gatsby, directed by Martin Scorsese. Eric and Sloan renew the friendship, with Eric wanting to be a little more than friends. However, Eric is truly ’playing the field’ as the boys often refer to his many different girls. Eric takes Sloan to the Gatsby premiere ’as friends’. Eric’s other client Charlie is cut from his show, much to Eric’s dismay. After rejection by Sloan, Eric chooses to see another girl Ashley exclusively, who appears to be quite star-struck with the movie star lifestyle.
Ari is having trouble with his new employee and friend Andrew Klein, who is cheating on his wife with a junior agent named Lizzie. Lloyd also seeks a promotion, which Ari promises if he can get through a 100 day ’hazing’ period, which includes tasks such as losing 15 pounds. After Turtle makes his red-carpet debut with Jamie-Lynn Sigler, he feels pressure from others that he is not good enough for her. Additionally, he is trying to start his own career, but after failing to get a business loan he decides to go back to school at UCLA Extension and learn how to properly start a business. Drama offers to pay for his schooling as a birthday gift.
When a monsoon damages the set of Vince’s upcoming film, production gets pushed back 12 weeks. With his newfound free time he wishes to travel, but Eric, Turtle and Drama all have their own agendas that don’t allow for a vacation. With Charlie being replaced on his television show, Eric once again finds Vince as his only working client. As a result, he decides to close The Murphy Group after admitting a lack of knowledge on how to properly run the business. Drama learns that his character on Five Towns will be getting a love interest, and asks Turtle if Jamie-Lynn would be willing to play the part. After some hesitation on Turtle’s part prior to asking her, she agrees to do it.
David Schwimmer comes in to the Miller Gold Agency to listen to pitches for television series ideas, but seems to particularly connect with Lizzie. He invites her out to lunch, which visibly makes Andrew Klein jealous. Ari and his wife had received a phone call the night before from Marlo (Andrew’s wife) asking if they had seen him. The following morning Andrew assured Ari that he was ending his affair with Lizzie. However, when David Schwimmer calls Ari and tells him Andrew crashed the lunch with Lizzie, Ari realizes it’s not over between them and finds Andrew having a mental breakdown in his car in the parking garage. he tells him to think of his family and how he doesn’t want to be seen by them as a liar. He misinterprets this advice and leaves Marlo.
Eric and Ashley’s relationship develops, and they become close to each other. Sloan calls Eric to tell him that she will be chairing the charity golf tournament that he and the boys are attending the next day. Ari and Mrs. Ari are at odds after Ari avoided telling her about Klein’s affair, and he tries to buy her back with a Maserati, which she rejects. Vince, Drama and Turtle play golf with Mark Wahlberg and Tom Brady at the tournament. Drama embarrasses himself due to his temper, and Turtle surprisingly forms a bond with Brady, who invites him and Jamie-Lynn to dinner. Eric plays golf with Murray Berenson (George Segal), a talent manager, and he offers Eric a job with his company. Eric turns the job down realizing Sloan had asked Berenson to talk to Eric. Eric and Sloan have a heated argument before Eric leaves. Ashley encourages him to take the job, asking why he won’t. He replies that he doesn’t know, and then accidentally calls her Sloan in a kind of Freudian slip.
Lil’ Wayne is expected to appear in an episode as himself. On March 6 2009, Dan Patrick of Sports Illustrated reported on his radio show that LeBron James would also make a cameo in an episode. Los Angeles Lakers’ center Andrew Bynum is also expected to cameo. Steve Nash, the point guard of the Phoenix Suns, has also revealed via his Twitter that he will also have a cameo appearance in the season premiere.[12] Aaron Sorkin recently confirmed on his Facebook Group he would be guest appearing on the show as himself. Israeli 2004 Miss Israel Gal Gadot will act as Vince’s girlfriend for several episodes. Kate Mara will be joining the cast of Entourage this season, TVGuide.com has confirmed. Mara will play E’s new assistant at his fledgling talent-management company, and perhaps his love interest as well. Also Zac Efron will be making a cameo as he was filming on June 1st, 2009 at the Hollywood NikeTown.[12] It was confirmed on 14th July 2009, that Matt Damon will be making a guest appearance on the show. Show favorite Jeremy Piven described seeing Damon on set as "The most surreal moment in the world".
Seventh season
On July 30, 2009, HBO renewed Entourage for a seventh season

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