Facing a possible lawsuit, Ari readies himself to do battle with Lizzie and her new boss, old foe Amanda Daniels. Vince puts his next big-budget movie in jeopardy with his antics, including a risqué online video. Turtle’s romancing of Alex does not go as well as he’d envisioned. A cleaned-up Billy Walsh returns to ask Eric about directing jobs – and comes up with new show idea for Drama, who’s been wallowing in self-pity.

Eric and Phil try to convince Drama that he has talent on the sitcom front; Ari resists Barbara's urgings to have Lizzie promoted; Turtle is intrigued by a business proposal from Alex; Scott Lavin continues to ingratiate himself with Vince.

E's new client Charlie gets his pilot script picked up, but the studio wants to cast E's arch-nemesis, Seth Green. Vince confronts Verner, the director of "Smokejumpers," who tells Vince to work on his bad habits. To help impress Babs, Ari and Lloyd give Andrew a Hollywood makeover.

Eric considers the management-company offer while trying to patch things up with Ashley after a Freudian slip. Ari finally gets Mrs. Gold to forgive him at home, but an appearance by Marlo Klein tests his resolve at work. Drama tries to protect Jamie-Lynn from a disreputable network executive.

Amanda gets angry when Vince and Eric procrastinate over the Edith Wharton movie. Turtle and Drama find some dream dates at the dog park.

"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.

Vince is impressed by porn star Sasha Grey and her literary knowledge, and ends up bringing her along to a meeting with Stan Lee. Suspecting that Lizzie is trying to steal his clients, Ari woos Jessica Simpson, Aaron Sorkin and Mike Tyson, but not before taking out his ire on Mrs. Ari. Turtle pitches Eric about Vince becoming the face of his new venture. Drama is anxious about his new series with John Stamos, especially after learning Bob Saget is eyeing his role.

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's fling with a 'cruelty-free' vegan named Fiona – and her friendship with a laid-back L.A. 'sherpa' – brings unexpected karma to the entourage. Eric pushes a promising new script set in Queens; Drama fears the disruptive power of his friends' new relationships; and Turtle barters boots for booty.

Seeking assurance that Vince’s life is under control, director Randall Wallace calls a meeting, but Vince parties a bit too hard the night before. Ari agrees to help Lizzie find a new job in exchange for some potentially damaging audiotapes. Turtle winds up in damage control after promising an L.A. retailer more product than he can deliver. Billy Walsh’s latest pitch leaves Drama indignant and Eric intrigued.

Eric is informed by Phil Yagoda (William Fichtner) that the network is interested in Drama’s show, though the star is not enthused about its content. In the wake of recent bad press, Ari attempts to fashion a kinder, gentler persona at work and home. When demand for Turtle’s tequila line outpaces production, he sets out to find new sources of funding. Vince tries to convince Sasha to turn down a high-paying offer to do another porn movie.

To keep her out of a porn film, Vince tries to land Sasha a part on his new movie. During a chance run-in with Queen Latifah, Ari finds out that Amanda Daniels may have landed a deal he’d coveted. Eric tries to get Drama on board for Billy Walsh’s series, and Eric’s assistant Jennie (Janet Montgomery) pitches in to help persuade him. Turtle’s efforts to find financial backing from Mark Cuban gets him in hot water with his Mexican boss.

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.

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.

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.

Turtle contemplates his future career path, and seeks out Ari for advice. Meanwhile, Eric gets nervous about Charlie’s pilot after getting some unsolicited feedback from his new fling.

Ari must face a public relations crisis over Vince's movie while meeting with top NFL executives; Eric agrees to help Drama find the perfect script; Turtle accuses Alex of maxing out his corporate credit card.

Ari tries to keep his wife's surprise party on track, the guys attempt to stage an intervention for Vince, and Turtle scrambles to find investors to save the tequila business.

Basking in the adulation from his latest movie premiere, Hollywood 'it' actor Vince Chase joins childhood pals Eric, Drama and Turtle to debate the pros and cons of attending their tenth high-school reunion back east. Meanwhile, Eric – Vince's de facto manager – incurs the wrath of Vince's agent Ari by advising Vince to pass on a script he hasn't even read. On the domestic-security front, Turtle agrees to test the mettle of the entourage's new guard dog, a Rottweiler named Ahnold.

Ignoring the cautionary portents of a negative review, Vince ramps up his already-excessive spending by leasing a new Rolls-Royce. Ari urges Vince to get a "real" manager, causing a wounded Eric to do some soul-searching. Meanwhile, Drama skips a "Vagina Monologues" rehearsal (go figure) to join Vince and the entourage at a wild party hosted by a sexy actress.

One of the names on the short list to play 'Aquagirl' exposes a secret from Vince's past that makes Eric feel slighted. Ari gets bumped from an important list. Drama and Turtle try to enjoy their temporary new house.

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 director of Vince's latest action film talks his star into doing his own driving stunt, agitating both Eric and Ari. Turtle's attraction to an underperforming employee named Alex threatens to damage his fledgling carservice business. Ari looks to add to his resume as "the biggest agent in the world" by eying an alliance with the NFL. Worried that his holding deal is about to expire, Drama pressures Lloyd, now his agent, to land him a project.

Turtle has a hard time trusting Alex; Drama gets off on the wrong foot with potential co-star John Stamos; Ari learns that Lizzie may be siphoning off some of his clients; Eric and Scott settle their differences.

The boys are back in town...and Ari, eager for a commercial project, pushes 'Aquaman' – but Vince isn't buying; Eric has an official title now, but his status is questioned when he has to make a 'sex date' with Kristen; Drama's agent may be moving up, but his head shots are stuck in the past; and Turtle, cranky about his new job, takes multi-tasking to a chaotic level.