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HBO’s Entourage works as a sitcom because of the consistency and predictability of its ensemble – the titular team of 20- and 30-something guys that toil (often unglamorously) in the background of a film star’s life in order to ensure his continued success and the resultant flow of money and women back to them. The show succeeds as a satire of the Hollywood institution because it follows suit, expanding its perspective to the larger group of people behind the machinery and revealing how they treat one another. The main characters are joined by a host of other compadres and competitors who form the ranks of the industry, including nearly every rung from the mail room assistant to the CEO of an enormous corporation. Within this system of codependent relationships, individuals are treated as brands, women are treated as objects, committed relationships are discouraged, and one’s word means nothing unless a contract is signed and a check clears.


To synopsize the show in this fashion is to identify the two competing visions at its heart. On one hand, the show provides a vision of fantasy lifestyle for those with dreams of fame and/or material success. Even the lowest achieving member of the entourage (Jerry Ferrara’s “Turtle”, the star’s chauffeur) lives considerably larger than an average middle class income could afford. On the other hand, the series warns that the pursuit of fame and wealth will hollow out the virtues that might otherwise keep one’s perspective balanced in the midst of such treasures. Unfortunately, the legacy of Entourage is tied much more to the former vision than the latter, and this imbalance of direction defangs the satire and dilutes the moral voice in some significant ways as the show progresses from season one (2004) to season eight (2011).


cover art

Entourage: The Complete Series

(HBO; US DVD: 6 Dec 2012; UK DVD: 11 Jun 2012)

Last July, on the eve of final season’s premiere, The Hollywood Reporter conducted behind-the-scenes interviews with the cast and creators of the show. Among the many anecdotes about the show’s success and relationship to pop culture were two quotations by creator Doug Ellin and executive producer Mark Wahlberg that seem to explain the show’s identity crisis and how it came to be. Both men hint at a more dramatic direction for the show’s pilot and early episodes, with Wahlberg admitting, “If they had done my version, it would have had a lot more violence and craziness that people might not have found entertaining. Ultimately, you want to feel good at the end of watching it. Too much of it would have been a downer.” In discussing his acceding to HBO’s insistence that “this should not be a story-driven show,” Ellin says, “I was like: ‘This is the worst script I’ve ever written. There’s nothing happening, they smoke some pot, they pick up girls.’ That was the script that got green-lit. Then we had to find a cast.”


While their present honesty is refreshing, Ellin and Wahlberg reveal what is perhaps a depressing truth about the system Entourage attempts to satirize: So slavish is its devotion to the lowest-common denominator viewer that HBO would rather knowingly invest in the most vacuous version of potentially successful material than take a risk in alienating an audience looking only to have a good time. For the initial seasons of the show, Entourage makes the best of the situation by having its characters wrestle with this very kind of quandary.


At the show’s beginning, rising superstar Vincent Chase (Adrian Grenier) is famously unbothered as he allows those around him to make decisions. He doesn’t seem to take his career very seriously, and his humble New York City roots make his Hollywood success that much sweeter. Along for the ride are Turtle, manager Eric (Kevin Connolly) and half-brother Johnny “Drama” Chase (Kevin Dillon). They live together as if in a fraternity, and their respective differences in status rarely interfere with the bonds of friendship. The season exists to showcase their partying lifestyle, their ease of access to exclusive people and places, and eventually, the burden of having to make decisions about one’s career.


The highlight of season one (and indeed most of the series) is Dillon’s performance as Drama. In a show full of inspired over the top roles and performances in supporting roles, Drama is arguably the most heartfelt character. His C-grade star is fading as Vince’s A-list status is taking shape. He’s a decade older than the rest of the group. His personality is a mixture of thinking-makes-it-so confidence and crippling insecurity that foils him at every turn. These internal conflicts and his own undying support of his brother make him the most human and frequently most sympathetic character in the early episodes of the series. The funniest material comes from his rose-colored remembrances of when he was a hot property in Hollywood (which in actuality amounts to some episodes of Melrose Place and a starring role on cult series Viking Quest). He has a way of referring to other Hollywood figures in abbreviated terms—Eric Roberts is “ER”, Jason Patric is “JP”, Celebrity Justice is “CJ”—that are emblematic of his own desperate attempts to appear on the inside track of the industry despite its distance from him.


Though Drama’s desperation isn’t the main focus of the series, it does share one important quality with the better episodes and seasons, which is the theme of being true to oneself and one’s own values regardless of the cost. Most of Vince’s dilemmas involve others telling him what’s best for him. None of these outside voices is as loud and insistent as that of Ari Gold (Jeremy Piven), an agent who serves as the fifth lead character of the ensemble. Piven’s manic, award-winning performance as Ari ensures that the agent would become more central to the plots after the first season, and many episodes of the series find Vince having to choose between following Gold’s advice or that of his friends and manager, Eric.


These career choices do inject suspense and excitement into the show, insofar as the audience vicariously experiences the consequences of choosing (often gambling) wisely or foolishly. Plots revolve around box office results, salaries and subsequent offers – all measures of success or failure routinely reported on in actual industry publications. It’s no coincidence that Deadline Hollywood becomes a major point of discussion by season seven. Vince’s path takes him from breakout star of a small film called Head On to the lead of hot independent film property Queens Boulevard to the superheroic heights of blockbuster franchise Aquaman before sending him back down the ladder with appearances in commercials and a disastrous drug epic called Medellin, which stalls his career for some time before an inevitable revival.


In between these career highs and lows, Vince and the boys do a lot of sitting around, smoking, drinking, and hooking up with ladies. As exciting a lifestyle this might be to viewers seeking an escape from everyday drudgery, a stasis begins to set in with many episodes that involve little more than the shenanigans and sexual misadventures of the boys themselves. This leaves the more interesting storylines to the series’ supporting characters like Ari, his assistant Lloyd Lee (the scene-stealing Rex Lee) and other Hollywood figures embodied by real actors in cameo appearances or thinly veiled versions of recognizable personas. Some of these appearances provide fun diversions:  Gary Busey torments Turtle on the beach after the boys disrupt his art show, Val Kilmer embraces his own reputation for druggy excess while playing a peaceful dealer whose mood turns paranoid on a dime, and Eric Roberts acts as a spiritualist/guide on a trip of enlightenment to Joshua Tree. 


The first truly great episode of Entourage is “Exodus”, which is the second-to-last episode of the second season. Ellin and Cliff Dorfman’s script provides a pivotal moment for Ari, as his absentee boss (Malcolm McDowell’s Terrance McQuewick) decides to reenter the picture at his agency and threatens to rob Ari of the fruits of his labor. Taking a cue from Jerry Maguire, Ari tries to find kindred spirits to follow him out of his agency and into an uncertain future, but it is only Lloyd (here the Dorothy Boyd to Ari’s Jerry Maguire) that accompanies him and keeps his hopes alive. That Ari is back to his nasty behavior in no time means he will be humbled many more times within the series, but “Exodus” manages the difficult feat of making us feel sorry for him.


“Exodus” is the culmination of season two’s focus on winning and losing. Other key points of the season include an early moment of self-awareness for Vince, as he advises Eric on the nature of success: “Sometimes your position in life allows you to get things you never could’ve had. That doesn’t mean it’s not right. And it doesn’t mean it’s going to last.” Later, Ari reflects on the relationship between success and fulfillment, offering up “Nobody in this town is happy except for the losers.” Indeed, the victories are never lasting, as they are accompanied by other setbacks and pitfalls. No season two arc illustrates this more succinctly than the way in which a successful Sundance screening of Queens Boulevard and Vince receiving James Cameron’s approval for the role of Aquaman are offset by receiving the spite of Harvey Weingard (the late Maury Chaykin playing a barely fictionalized version of Harvey Weinstein).


Season three, running 20 episodes, is the longest and also the most satisfying season of Entourage. With the arrival of Aquaman, Vince achieves superstar status, but he also commits to staying level-headed. He and the boys spend the evening of the film’s release with teenagers at a high school party. In another episode, hometown friend Dom (Domenick Lombardozzi) unexpectedly drops by after being released from prison. His presence creates an identity crisis for Eric, Turtle, and Drama, as Vince seems to allow his ruffian friend to take their places at will. Lombardozzi walks into the series like a young Tony Soprano, and his presence shakes up the stasis in an entertaining manner.


These and other season three events, such as Vince’s siding with Queens Boulevard director Billy Walsh (an electrifying Rhys Coiro) over the studio’s butchering of that film, illustrate the degree to which it’s possible to retain one’s sense of self even in a pressure-cooker like Hollywood. Likewise, the negative consequences of not compromising (Vince losing the Aquaman sequel to another actor) are satisfying on a dramatic level, because they test the characters’ integrity. The most inspired season three arc involves Bob Ryan (Martin Landau) as a Robert Evans-era producer who Ari manipulates into thinking he’s relevant again. Ari revives Bob mostly as a way to punish Eric, but the episodes featuring the old-school producer illustrate that the ethics of Hollywood have indeed changed. Sure, the place might have always been a sort of Babylon, but it’s now cutthroat to the point of being unrecognizable to Bob, from whom the young upstarts could learn a thing or two if only the town had enough patience for him.


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