A Show Divided: ‘Entourage’ as Satire and Misfire

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).

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.

An Aura of Fascination

The fourth season is entertaining mostly for its focus on Billy Walsh, who is a composite of young director personas like Paul Thomas Anderson, Vincent Gallo, Rob Weiss, and Troy Duffy. Much credit must go to Coiro for creating a character whose passion for his craft makes us forgive any number of terrible flaws in his personality. His contempt for the business (the class of Hollywood he refers to as “suits”) is not unwarranted, given some of the underhanded moves we’ve witnessed heretofore in the show. Alongside Billy’s condemnation of the business are signs of softening from the chief suit, Ari, who begins to reciprocate some devotion towards Lloyd and (beginning in season five) his old friend Andrew Klein (Gary Cole). Ari will come to regret nearly every one of his good deeds, but like Vince’s failures, they test his constitution.

And Vince does fail spectacularly with Medellin, the dream project that bridged several seasons of Entourage before finally being realized by Billy. As with many popular culture characters and concepts on the show (such as Frank Darabont’s fictionalized foray into television ahead of now-megahit Walking Dead) Medellin foretells real life. In this instance, the epic film shares many connections with Steven Soderbergh’s Che, which would later be created and released under similar circumstances. But even compared to the bloat and bad box office results of Che, Billy Walsh’s opus is a notorious, career-ending bomb. As such, the beginning of season five provides an opportunity to send Vince and his friends into serious reconsideration of their careers, but nonchalance and an embrace of the party lifestyle win out. Though Eric and Drama are working, Vince and Turtle go off the grid in a hedonistic “paradise”.

Rather than pursue the existential direction that would better align with Mark Wahlberg’s “downer” version of the show, seasons five and six are a balance of nostalgia for aspects of the earlier seasons and a more concentrated focus on romantic relationships. Dom returns briefly, the boys follow their hearts back to New York by season’s end, and Turtle begins an unlikely relationship with Jamie-Lynn Sigler (appearing as herself). In terms of the growth of the characters and their goals, the fifth season could well be (and in retrospect should have been) the final season. There’s a wonderful moment in episode seven, in which Ari and Vince are each leaving on jets and have a sensitive parting of ways. In this show about relationships, this scene is the best single distillation of a relationship having run its course and of the need to accept such a change.

The final three seasons of Entourage diminish the show’s reputation, first by treading too-familiar plot territory and then by revealing the moral paradox of its competing visions. Season six begins with Vince having overcome his cold streak and being a hot property once again. With little more to do with its protagonist, the show becomes a succession of briefly entertaining, but generally boring tales involving Eric and Turtle’s love lives. As in season one, Drama is the heart of the series. His attempts to defend Jamie-Lynn Sigler’s honor threaten his position on hit show Five Towns, which was his hard-won casting victory after years in the wilderness.

By any measure, season seven is the worst Entourage has to offer. From its inception, one of the persistent flaws of the show is its overcompensating inclusion of what might be called eye candy. The best use of this technique is the show’s casting of young actresses as themselves. This allows Ali Larter, Jessica Alba, Anna Faris, Jaime Pressly, Mandy Moore, and Jamie-Lynn Sigler, among others, to playfully embody versions of their real-life personas and (to varying degrees) have control over the events of the plot. By contrast, there are the scores of nameless women who only exist to parade naked across the screen or engage in completely gratuitous sex scenes with Vince.

Related to this latter tendency is the show’s habit of indulging male celebrities hoping to increase their own image as Lotharios. Of these, none is more pathetic or reeks of greater desperation than Bob Saget, a man who has spent the past several years trying to sully his Full House image. Never have his efforts appeared more pathetic than they do in his many appearances on Entourage. Within that context, season seven might be best described as one that could have sprung from the calculatingly filthy mind of Saget himself.

In season seven, the female lead and object of Vince’s obsession is pornographic performer Sasha Grey, appearing as herself. Never once does the show provide any convincing evidence for why he and the rest of the guys are so impressed by her, and Ellin’s own reported excuse is hardly convincing: “Sasha’s the biggest porn star in the world right now, and when Soderbergh casts her as the lead of his movie, I take notice.” The Soderbergh movie he refers to is The Girlfriend Experience, a movie in which Grey plays a prostitute in a bit of stunt casting that at least raises interesting questions about the monetary value of loveless sex.

But other than attempting to capitalize on her “brand”, Entourage makes no such intellectual commentary on the sex industry and uses Grey to scrape the bottom of the dirty joke barrel. Moreover, her insistence that Vince “not treat [her] like a whore” is stunningly tone-deaf, given the very behavior the show celebrates. By contrast, season one featured a storyline about Justine Chapin (Leighton Meester), a young pop star whose popularity stemmed less from the quality of her music than from her public commitment to remaining a virgin until marriage. Justine is a character modeled after several young pop stars (male and female), for whom the (PR-aided) decision to publically identify as chaste creates an aura of fascination. Vince, attracted to Justine, is intrigued by what he cannot have, and Entourage makes a clever point about the capital of purity within popular culture.

Justine is she show’s lone virgin, and Sasha Grey is at the opposite end of the spectrum, yet the show refuses to be similarly honest about the lifestyle she represents. Complicating the season’s already muddy view of women is a subplot about Lizzie Grant (Autumn Reeser), a rogue associate of Ari’s who is threatening to release audiotapes of his bigoted and misogynistic tirades. One wonders what to make of her feminist activism on a series that began with a relatively shallow view of women and now views female sexual health through the lens of Sasha Grey, who is famous for being abused on camera. And if Sasha Grey is the new Mandy Moore, then what does that say about the options for young women in Hollywood?

In addition to the Vince/Sasha nosedive, season seven stumbles by giving Vince a wholly unconvincing hard drug habit. This turn of events would have been better motivated had it occurred in the immediate aftermath of the Medellin disaster. Yet here, the show more or less excuses the star’s slide into substance abuse by suggesting it began after a mild on-set accident left him injured and in need of pain medication. Though Grenier is quite good in the scenes that depict him as under the influence, the plot itself is unpersuasive. The only aspect of the season that works is the return of Billy Walsh, now reformed and at peace at the very moment his former leading man is spiraling downward. The irony is heavy, but Coiro and the writers play the counterpoint effectively.

One can see in this second-to-last season an attempt to shake up the fading series by a sharp turn towards the gloomier version the show might’ve been all along. But the producers, writers and directors go about doing so in nearly all the wrong ways. Instead of heightening dramatic situations that are already part of the fabric of the show, the approach is to appeal to an even lower standard of behavior with a series of tangential plots about pornography, cocaine, and tequila, and recurring cameos from Bob Saget, Mark Cuban and Eminem, none of which adds any life to a flat-lining season.

That the final season of Entourage corrects course is unsurprising, because it’s impossible to do any worse than season seven. Between Billy’s calming presence, a rehabilitated Vince, and the increasingly entrepreneurial Turtle, there’s a sense that the boys are finally, belatedly growing into their adult selves. Ari’s family life threatens to slip away in the form of a divorce, and that motivates him (more than any previous setback) to get his priorities straight. The high point of the season plays like a scene out of Hurlyburly, as producer Carl Ertz (Kim Coates) has a drug-fueled meltdown during a meeting with Vince and Turtle. Coates’ acting in the episode momentarily elevates the show into something much more profound, and one wishes the mode of storytelling that houses his character would’ve been part of the show’s arsenal from the beginning.

From there, the series overcorrects, as if atoning for the aimlessness and raunchiness of season seven. Entourage has been criticized and parodied as a show too rife with unrealistically happy endings, so the bold choice would have been to go out on a note of some uncertainty. Yet the last episode throws forth romantic reconciliations, weddings, a pregnancy, and other life-changing bits of happiness that converge in a manner unconvincing for even this optimistic series. Longtime viewers might bid adieu with well wishes for the characters’ happiness, but to do so uncritically is to sweep under the rug the many habitual behaviors that complicated and compromised these (occasionally) dynamic characters each time they faced big decisions.

Furthermore, when considering how forcefully the show has argued against meaningful, monogamous relationships, it’s unlikely that this group of characters would all achieve lasting happiness simultaneously. I commend Entourage for trying to send its characters off into respectable and fulfilled futures, but the finale reads as a last-minute attempt to inject moral insight into a designedly shortsighted series.

To be fair, perhaps it isn’t realistic to expect a show like Entourage to display the caustic satire of George Huang’s Swimming with Sharks or the philosophical probing of Michael Tolkin’s Player novels or Paulo Coelho’s The Winner Stands Alone. And to review the entire series in a short period of time is to become aware of how much the show does to expose the moral and ethical failings of Hollywood. However, scratching the surface of what’s wrong with the business isn’t the same thing as following through on that awareness with deeper questions about why anyone bothers subjecting himself/herself to such insecurity and venality.

Rumor has it that a feature film is on the horizon, and the post-credits scene of the final episode points to an intriguing direction for that film. While on an extended vacation with his wife, Ari receives a phone call from John Ellis (Alan Dale), a fictionalized chairman/CEO of Time Warner. Intending to retire, John offers Ari his own job. His pitch is, “If you want to know what heaven really is, Ari, try being God.” For Ari, whose quest for power and dominance has been momentarily alleviated by the realization of filial happiness, this is a temptation that would be monumentally difficult to ignore. If the movie pursues that plot, then perhaps greater existential trials await Ari and the boys of Entourage. Maybe the happy ending of the series was just another trick to lure them all back in.