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 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.

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.

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.

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.

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.

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.

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.

Vince discovers why his gorgeous neighbor Staci has been so friendly. Eric regrets the past when he has to get through yet another gate kept by Emily. Ari tries to blackmail Dana into getting a meeting with an important director. When Drama and Turtle curb their spending, Vince grows suspicious.

After meeting a talk-show host at a boxing after-party in L.A., Vince agrees to appear on his show – despite a long-standing rift between the host and Drama. Eric and Kristen share a long goodbye; Ari puts the full-court press on a famous comic; and Luke Wilson tells Turtle how to score a free home-theater system for Vince.

With production on his next film delayed, Vince searches for ways to amuse himself. Andrew tells Ari he's ended his affair with Lizzie, but Ari has Lloyd keep an eye on him anyway. Drama auditions actresses to play his new love interest on "Five Towns"; Jamie-Lynn takes Turtle shopping for back-to-school clothes; and a bored E contemplates his next move.

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.

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.

Shauna goes into damage-control mode when Vince must pass a drug test after being caught in a compromising position. Ari escorts an old flame to Bobby Flay's restaurant to get back at his wife following a rancorous session of couples therapy.

Vince decides to celebrate the opening night of his latest movie, 'Head On,' with a group date – to Eric's chagrin. Drama's pumped-up gal pal Tanya struts her stuff at a bowling alley; Turtle taps into Vince's fan mail for some action; and Vince turns on the charm with unsullied pop vixen Justine Chaplin.

As Vince and Turtle are carried away by top-dollar decorating, Eric is anxious to get an offer in writing; Drama decides on elective surgery to 'augment' his livelihood; Ari breaks a deal in therapy with Mrs. Ari; and hotshot director Billy has big news about 'Queens Blvd.'

Within moments of arriving at Sundance, Eric lands a lunch with studio bigwig – and gets an offer for Vince that might be too good to refuse. Ari advises him to play it safe, and Vince wants to roll the dice. Turtle and Drama don't want to share.

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.

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 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.