12 Episodes 2008 - 2008
The fifth season of the hilarious Hollywood satire finds the guys trying to help Vincent Chase (Adrian Grenier) pull out of a career free fall after the flop of his film "Medellin." As the season opens, Vince and Turtle (Jerry Ferrara) lay low in tropical paradise, while back in L.A., manager Eric Murphy (Kevin Connolly) and agent Ari Gold (Jeremy Piven) do damage control. Upon his return to Hollywood, Vince sees his situation go from bad to worse as his accountant advises him to file for bankruptcy. Though Vinnie seems to have lost his mojo, things are looking up for Eric, who shops around a promising script written by two rednecks (Giovanni Ribisi, Lukas Haas). But negotiations become tense when the better offer comes from a studio that doesn't want Vince in the film. Meanwhile, Ari takes a big gamble, literally, to help Vince while playing golf with a big-time studio head. And later the cocksure agent contemplates a dramatic career move. Speaking of Drama, Johnny (Kevin Dillon) continues his long-distance romance with Cannes fling Jacqueline (Julia Levy-Boeken), makes a memorable appearance on "The View" and hires Turtle as his personal assistant. Despite that professional low point, Turtle's personal life improves considerably when he lucks into a seat next to Jamie-Lynn Sigler on a flight back home to Queens, where the boys head to regroup. The season-ending trip reveals whether Vince's star rises again, and discloses one of the series' best-kept secrets: Turtle's real name. Among the celebrities making cameos in Season 5 are Tony Bennett, Phil Mickelson, Whoopi Goldberg, Jeffrey Tambor, Eric Roberts, Peter Berg and executive producer Mark Wahlberg.
Sun, Sep 7, 2008 30 mins
In the fifth-season premiere, Eric and Ari deal with the fallout from "Medellin"'s wretched reviews while Vince and Turtle lay low in an undisclosed tropical paradise, and Drama continues his long-distance romance with Jacqueline, but turns into a diva during a "Five Towns" photo shoot.
Unlike a Virgin
Sun, Sep 14, 2008 30 mins
Ari worries about coming clean with Vince about the precarious status of his career; Eric turns to a former associate to shop a promising script; Drama pays a price for his obsessive contact with Jacqueline. Tony Bennett and Mark Wahlberg appear as themselves.
The All Out Fall Out
Sun, Sep 21, 2008 30 mins
After being advised by his no-nonsense accountant to file for bankruptcy, a cash-strapped Vince reluctantly considers a paying gig at an ostentatious Sweet 16 party; Ari raises the stakes in a battle of one-upsmanship with rival agent Adam Davies.
Sun, Sep 28, 2008 30 mins
Ari and Vince visit studios to pitch the smoke-jumper script, while Eric has tense but separate negotiations with Amanda and the screenwriters; Drama makes a memorable appearance on "The View."
Sun, Oct 5, 2008 30 mins
Making the right call on a crucial career move calls for Vince and the guys to search for clarity and guidance in the arid expanse of Joshua Tree National Park. Meanwhile, Lloyd assists Ari in his time of need.
Sun, Oct 12, 2008 30 mins
Dom needs Vince's help after being involved in a televised car chase; Ari wagers on Vince's career while playing golf with studio head Alan Gray; and a desperate Turtle signs on as Drama's personal assistant. Golfer Phil Mickelson has a cameo.
Gotta Look Up to Get Down
Sun, Oct 19, 2008 30 mins
Vince works with a supermodel on a photo shoot for a major fashion house, and Ari seizes an opportunity at a funeral to boost his client's career.
First Class Jerk
Sun, Oct 26, 2008 30 mins
Ari's preoccupation with a huge career move makes him inaccessible, so Vince answers a rival agent's call to meet with a famous director. Meanwhile, Turtle lucks into an airplane seat next to Jamie-Lynn Sigler.
Sun, Nov 2, 2008 30 mins
Vince's first day on the set of "Smokejumpers" includes feelings of nervousness and a meeting with costar Jason Patric. Meanwhile, Ari reaches out to an old friend (Gary Cole) who needs his help.
Seth Green Day
Sun, Nov 9, 2008 30 mins
Vince is unnerved by stern advice from Verner (Stellan Skarsgård), the demanding director of "Smokejumpers." Meanwhile, Eric is dismayed to learn that Seth Green is on the short list for Charlie's pilot, and Andrew receives a makeover from Ari and Lloyd.
Play'n with Fire
Sun, Nov 16, 2008 30 mins
Vince gets confusing direction from Verner during a crucial scene in "Smokejumpers," and Turtle sets up a secret meeting after receiving an out-of-the-blue call.
Return to Queens Blvd
Sun, Nov 23, 2008 30 mins
In the fifth-season finale, the guys return to New York City, where Vince looks up an old flame, Eric tries to persuade Gus Van Sant to give a part to Vince, and Drama mulls an investment opportunity.