After hitting a few speed bumps the past couple of years, Vincent Chase's career has kicked into high gear after his role in the latest Martin Scorsese film. But now that Vince is back on top, is it finally time for Eric, Drama and Turtle to step out of his shadow? Hit the gas for another electrifying season of 'Entourage,' HBO's hit series about a hot young actor and the three buddies he's brought with him from their hometown in Queens, NY.
On the eve of the 'Gatbsy' premiere, Eric's been on a hot streak, Vince is about to take his driving test (in preparation for playing Enzo Ferrari), Turtle's going strong with Jamie-Lynn and Drama's still hanging around Vince's mansion in spite of having his own place.
The gang helps Eric move into his new place and E invites Sloan to accompany him to the 'Gatsby' premiere that night, insisting it's just as "buddies." When Ashley drops by later with a housewarming gift, Eric brushes off her queries about his plans for the evening, telling the guys he doesn't want her to get ideas about being his girlfriend — he wants to be single right now. Ari pushes Mrs. Ari to take Andrew Klein's wife Marlo on a mani-pedi date wanting their wives to be friends. In spite of Andrew's doubts, the two women hit it off. At Miller-Gold, Andrew pulls Ari into a meeting set up by agent Lizzie Grant with two showrunners — Ari picks up on Andrew's flirtation with the junior agent and warns him to stay away. At the premiere, Ashley surprises Eric by showing up. Eric confesses his real feelings for Sloan but she tells him she can't just jump back in and he counters that he can't just be friends. Ari confronts Andrew and Ari orders him to end his fling with Lizzie. Back at Vince's mansion, Eric gets a call from Ashley and decides to console himself with her, leaving Vince, Drama, Turtle and their dates to continue the party.
Nervous about the test-screening for his client Charlie's new sit-com, Eric is upset when he learns that Ashley doesn't find Charlie likeable. Meanwhile, it's Turtle's 30th birthday and the day begins with a phone call from his mother who chews him out for looking like a loser in People magazine — wearing sneakers to the premiere with Jamie-Lynn. Vince tries to cheer him up by taking the gang driving on a local racetrack and then giving Turtle the keys to a new Ferrari. Vince realizes he should have "coagulated" with Jamie when she shows up with her own gift: a Porsche. Lloyd continues his 100 days of hazing — memorizing Ari's clients' favorites drinks. E comes by to talk to Ari about Vince's latest film offers and gets the scores from the test pilot while he's there — they want to replace Charlie. Later, Turtle shows up asking Ari for career advice in the form of potential investors for a business he wants to start. But Ari gives him a speech about the hard work needed to be a self-made man. E avoids Charlie's calls and holes up with Ashley to figure out what's wrong with the pilot. He finally realizes that Charlie sucks — but that Eric needs to sell his client anyway. After getting advice from Ari on how to lie, E storms into Amy Miller's office but fails miserably. At his birthday dinner, Turtle and Jamie announce Turtle is going back to school at UCLA extension for business management.
Eric watches the late-night box office returns for 'Gatsby' and Ari calls to revel in Vince's success — and to report that Vince's next film is being pushed several months. As soon as he hangs up, Ari and Mrs. Ari get another call on the home line from Marlo Klein, looking for Andrew. Ari covers for Andrew but later at work he warns him things better be over with junior agent Lizzie Grant. Andrew assures him they are and he's all about the work, but when David Schwimmer shows up for a meeting, it's Lizzie who piques the actor's interest and Andrew's jealousy rears its head. Vince debates what to do now that he has a hiatus and is disappointed that all of the guys are too busy with their own lives to travel with him. He consoles himself with a waitress, and Facebook. As they kill time, Eric complains to Ashley about how bored he is with Vince being his only successful client and she challenges him about what he really wants. Meanwhile, when the casting session for the role of Drama's girlfriend on 'Five Towns' is a bust, Drama begs Turtle to ask Jamie-Lynn to do it; Turtle refuses but later has a change of heart. Lloyd alerts Ari that Andrew is weeping in his car. Ari intervenes in Andrew's meltdown and orders him to think of his family — but later learns that Andrew interpreted his advice to mean he should leave Marlo. Mrs. Ari is furious with Ari when she hears from Marlo. Surprising the guys, Eric announces he's shutting down the Murphy Group.
Eric and Ashley's dinner is interrupted by a call from Sloan, who gives E a heads up that she's co-chairing the charity golf event he's attending with Vince and the guys the next day — Eric withholds that news from Ashley. At the golf tournament, Vince and Drama are paired with Mark Wahlberg and Tom Brady, and Sloan informs Eric that uber-manager Murray Berenson requested him. Ari tortures Lloyd by making him caddy for his team, which includes Jeffrey Tambor, who cheats to impress his two sons. Drama makes a fool of himself trying to win his wager to outplay his teammates. Turtle, being a loyal Giants fan, psyches himself up to tell Tom Brady off, but when Tom suggests Turtle and Jamie-Lynn should join him and Gisele for dinner, he melts. Mrs. Ari calls her husband, wanting to know why he's trying to buy her off with a new Maserati rather than just say he's sorry, but Ari insists it wasn't his place to confide about Andrew's affair. Murray tries to get E to come work for him, but when Eric discovers Sloan was the one who recommended him, he has doubts. Later that night, mulling over the job offer with Ashley, Eric mistakenly calls her "Sloan."
Turtle and Vince watch as Jamie shoots her 'Five Towns' love scene with Drama. E shows up late, having had a rough night after calling Ashley "Sloan." Ari finally convinces Mrs. Ari to accept his apology, but his problems aren't over: At Miller Gold, Marlo Klein tears through the offices in search of Andrew's "whore." Ari gets rid of her and has Lloyd track down Andrew and Lizzie, intending to fire them both but Lizzie insists it's over. Ari orders Andrew to go back home to Marlo. E goes to Ashley's to apologize, but as he's showering after their make-up sex, Ashley listens to a voice message he gets from Sloan. Realizing Sloan was responsible for his new job offer, Ashley storms out. Eric meets with Maury Berenson and accepts the job with his management company. Studio exec Dan Coakley shows up on set to meet Jamie-Lynn and invites her to lunch to discuss future projects. Drama gets protective and follows them to spy. While Turtle is at his first day of school, Vince kills time with co-eds and gets updates from Drama about Jamie-Lynn's lunch date. Back on set, when Jamie-Lynn hasn't returned, Drama works himself into a frenzy, storms Coakleys' office and tries to choke him. Coakley threatens to have him killed — by the writers. When E shows up at Ashley's that night she accuses him of still having feelings for Sloan and he admits he does.
Vince's mansion is broken into in the middle of the night. While the cops see no sign of an intruder, the maid discovers all of the guys' underwear has been stolen so Ari urges Vince to call his security guy. Lloyd informs Drama that he's not needed on set that day and the guys tell Drama to suck it up and apologize to Dan Coakley. Eric starts his new job and immediately bumps up against fellow manager Scott when he mentions he knows Bob Saget (who Murray is eager to sign). When Saget will only talk to E, and demands to have sex in Murray's office as a stipulation for signing, Scott makes E take the offer to Murray who ultimately agrees. After several failed attempts at apologizing, Drama finally grovels in person and Coakley tells him he's not firing him — he's going to torture him instead. Meanwhile, Vince and Turtle go gun shopping thinking they can handle security themselves, but are dismayed by the 10-day waiting period. When Drama brings some guns home and one goes off, Vince decides it's time to call in the pros.
Eric cuts short a call from Sloan, who wants to make sure E's not angry with her. He runs off to meet with Vince and the Israeli security team. Vince and the guys wonder if the Fort Knox treatment is really necessary. At Miller Gold Ari finds Andrew passed out on his office couch because Marlo kicked him out and blocked his credit cards. Barbara Miller wants Andrew fired if he doesn't sign Aaron Sorkin by the end of the day. Sloan invites Eric for a friendly drink and even though she admits she's seeing someone, he agrees. When Marlo won't let Andrew back in the house to get his Sorkin notes — and then torches them — Andrew drives through the front window and ends up in jail. Eric gets a call from Ashley just as he's meeting Sloan and ditches on drinks with her, telling Sloan he doesn't want to mess things up with a girl he kind of likes when Sloan is sending such missed signals. Ari makes Andrew pitch Sorkin from jail and when Andrew breaks down, Sorkin takes pity on him and agrees to sign, much to Ari's surprise. E makes up with Ashley. Meanwhile, the security team finds a driver's license in Vince's couch cushions — has his stalker been found?
Vince and Turtle are upset about the security team's takeover of the mansion, but when the driver's license found in the couch leads to a guy with a dubious past, Vince decides the security is worth the hassle. Turtle and Drama call E to meet Vince at his fitting for the Frank Darabont film and Ashley grows suspicious of his cryptic replies. Ari steals Zac Efron away from Adam Davies, and Adam retaliates by offering Lloyd a job as an agent. Lloyd rejects the offer, but reconsiders when Ari more than doubles his hazing period. Lloyd finally quits in a rage, abandoning Ari's smashed-up car in Beverly Hills. When Drama learns that the alleged stalker works at The Pleasure Chest, a store he used to frequent, he takes matters into his own hands. Just before he's about to go Rambo on the guy, he gets a call from Vince: Turtle has discovered that Vince's stalker is actually a bunch of sorority girls who were ordered to steal "Jamie-Lynn Sigler's boyfriend's underwear." Ashley meets Eric's assistant and the green monster rears her head, again.
Turtle frets over his unclean thoughts about the sorority girl, given his devotion to Jamie-Lynn. When Drama runs into the producer of 'Melrose,' (who canned him) and he suggests there's a part in 'Melrose 2009' that Johnny would be perfect for, Drama contacts Lloyd to see if he can get out of his 'Five Towns' contract — and discovers Lloyd has jumped ship. When Ari learns that Lloyd's gone to Adam Davies, he goes ballistic, and Drama benefits from the tug of war between Lloyd and Ari. Ari gets Drama off 'Five Towns,' but Lloyd makes an impassioned plea to remain his agent. Drama grills Ari about whether he believes in his talent — and Ari lets him go. Eric goes to Ashley's and learns she's suspicious about the identity of "Rupert Pupkin" (the name she saw on his cell phone). She insists she's not normally jealous and suggests she be able to read his emails to re-establish trust. Eric agrees, but has second thoughts and ends up breaking up with Ashley. Meanwhile, Jamie-Lynn gets a new series...shooting in New Zealand.
Eric is distressed to learn he and Drama shared a conquest...and even more upset when he finds out she's "slutty" and he didn't wear a condom. He gets tested for an STD. Ari continues to go through Lloyd replacements and is surprised by a visit from Terrance McQuewick, who gives him 24 hours to consider buying his agency, TMA. As Jamie packs for her New Zealand gig, she wonders how she and Turtle can make a long-distance relationship work, especially after she gets jealous of his new co-ed Facebook friend. Turtle is stunned when she breaks it off with him at the airport, insisting she doesn't want him to resent not being able to see other people. Drama has a meltdown at the new 'Melrose' audition and ends up in the hospital. Even though Lloyd gets him a do-over audition, Drama passes, insisting he needs to re-evaluate his choices after this scare. Ari tries to get dirt on Terrance from his trophy wife, Melinda, who reveals that they're divorcing — information that allows Ari to drive Terrance's price down to $75 million. Eric gets a clean bill of health and announces he wants Sloan back.
With Vince leaving for Italy the next day, Drama's the only one free to go with him. At couples counseling, Mrs. Ari objects to Ari using $12 million of her money to buy out TMA, suspecting it's more about revenge than good business. Ari gives an impassioned speech, winning her over. Matt Damon, Bono and LeBron James guilt Vince into giving a substantial donation to Damon's charity for kids. At the contract signing, Terrance springs the news of an addendum — that the new firm must retain the name of TMA — and Ari walks out. Drama reconsiders his "no" to the Melrose audition and kills it, but still gets turned down for being too old. Instead, he gets a holding deal from the network, so they can develop a series for him to star in. Eric whisks Sloan away to lunch to profess his love — and she gets furious. She accuses him of not being able to commit, but he insists this time he's in for real, producing an engagement ring. When Turtle realizes that even the hot co-ed can't distract him from his feelings for Jamie, he decides to go after her. On the plane to New Zealand though, he gets a call from her, insisting he not come. As the plane takes off, he buckles up for a long flight. Meanwhile, Terrance and Ari make peace and the deal goes through...then Ari goes postal at TMA, paintballing all of the agents he's firing — and giving Lloyd a reprieve. When Lloyd goes to tell Ari off, Ari offers an apology and an agent position, with an office. E and Sloan show up at the airport to see Vince and Drama off — and announce their engagement.