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My Journey to the Heart of Darkness in ‘Entourage’

HBO’s long-running bro saga was atrocious television, an artifact of post-9/11 American rot. But it got one thing right: It accidentally revealed the ways shitty men fail upward.

After spending my twenties in New York, I couldn’t wait to move to L.A. The standard reasoning applied: no wet stink of the crowded subway, no sixth-floor walkup, no long and miserable winter. I’d have a car, and I could drive to the beach, or mountains. The weed, the sun, the art, the food, the wild beauty of the West Coast stretching hundreds of miles north and south.

In fact, I had every reason to relocate — except for the one that most defines this city: Hollywood. I didn’t want to break into film or TV, as a writer or performer. I wasn’t in a band, nor was I trying to monetize myself on social media. I certainly harbored no aspirations of modeling. At 30 years old, I wanted a break from striving, and to continue at the work that paid. As an author friend already there told me, L.A. makes you dumber, and then, as a result, happier.

Four years later, I know there is wisdom in what she said. Yet I still cannot fathom how dumb, or how ignorantly blissful, you’d have to be to enjoy one of HBO’s most popular series of the aughts, which happens to be set in and around the tacky jungle of Hollywood climbers. It’s an exercise in whiteness, an ode to the mediocre, a stunning atrocity against television.

Please understand, I never wanted to see Entourage. It aired from July 18, 2004 to September 11, 2011, capturing a significant audience in George W. Bush’s second term before limping to a finish in Barack Obama’s first, an eight-season span that covered my college years and beyond. At no time in that period did I have HBO, nor was I impelled to borrow the DVDs on Netflix, and if my friends were watching (or pirating) the show, I had no inkling of their shameful secret. In the decade since, pop-cultural memory seems to have assigned it the reputation of a needlessly long and offensive fart. Had you asked me a month ago what Entourage is about, I might have guessed: “Jeremy Piven screaming into a cell phone.” 

The truth, I discovered, is that and worse.

In case you were never a fan, and your sadistic boss hasn’t forced you to stream Entourage for a nostalgia think piece, let me catch you up to speed: The sitcom follows ascendant actor Vincent Chase (Adrian Grenier) and three guys riding his coattails — his older half-brother and washed-up TV player Johnny “Drama” Chase (Kevin Dillon); his best-friend-turned-manager Eric Murphy, or “E” (Kevin Connolly); and another childhood pal, Salvatore “Turtle” Assante (Jerry Ferrara), who starts out the series as a lowly gofer, driver and all-around lackey. All four have come to Hollywood from humble beginnings in Queens, New York, and are incapable of letting this detail go unspoken for more than five minutes. Piven is the whammy for this dull ensemble, and our true creature of the industry, Chase’s agent, the always apoplectic and insatiable Ari Gold. 

Theoretically, the plot concerns the wheeling and dealing of the entertainment machine, the breakneck vicissitudes of a life in the spotlight (and the studio system), and the urge to prove manliness with material, independent success. In practice, however, Entourage is a televisual lad magazine full of big tits and glossy cars, an answer to the question “What if my bro were rich and famous?” Turns out you’d leverage his status to claim your own, mostly while scrounging for one-night stands. 

Fittingly, the pilot opens with Turtle, an immediate disgrace to the noble reptile, walking into a posh restaurant and, as a Wikipedia editor so tactfully phrases it, “greeting every female by name as he goes.” From that intro forward, Entourage isn’t so much “guys being dudes” as guys adrift in a sea of women’s hyper-toned bodies, appraising them, coveting them, and clinging to the delusion that this proximity is earned, correct or altogether inevitable.

The term “failing upward” has been useful in discussing how white men are constantly rewarded for their mistakes, and this mechanism is the crux of Entourage as well. Although Vince’s career should be a high-wire arc — each decision puts millions of dollars and his future cachet at risk, often prompting Eric and Ari to butt heads over strategy while Turtle and Drama break off in search of hand jobs or whatever — there are no wrong calls, and any evident fuckup is quickly set aright by some coincidence that elevates Vince and his bros higher still. 

It’s a formula hard to separate from the needs of a half-hour serial comedy, and under other circumstances, we gladly submit to the narcotizing effect of problems working out in the end. Yet to witness this pack of charmless dimwits claim triumph upon triumph, toasting each other with yet another round of shitty domestic beers, is soon unbearable. What you wouldn’t give for them to go down in flames.

It might be different if the group had any scrap of charisma to share between them. Vince is the blank where a character should go, hopping from starlet to starlet and delegating the rest. E is positioned as the straight man with a brain, but as he keeps striking the same weaselly note, you grow disgusted by his smug and superior airs. Drama is, perhaps, a genuinely tragic figure; seeing him kicked out of the Playboy Mansion for a past indiscretion in Season Two is about as close to pathos as we ever get, though of course it’s just a misunderstanding rectified at the expense of Pauly Shore, and Drama is largely immune to embarrassment anyway. Turtle is a dozen stereotypes of the horny, chubby wiseguy rolled into a backward-hatted Yankees diehard, and his reward is to eventually date Jamie-Lynn Sigler, best known for portraying Meadow Soprano in The Sopranos, who obviously deserved better in both the real and fictional world.  

To hope for an escapist or vicarious thrill by watching these clowns burn money and chat up bombshells on the Sunset Strip, in Beverly Hills and at Malibu parties is to unfairly punish yourself. They are simply too boring to convince you they’re having fun, and indeed Entourage showcases the trappings of celebrity as a garish sort of prison where you can never stop scheming and schmoozing — you’d argue it was satire if anyone faced consequences at some point. 

Truly, the “pleasure” of seeing Vince cavort with Mandy Moore is equal that of watching Turtle play Xbox (yes, there’s a B-plot about this). Piven, as Ari, gives us the only reliable spice, except it’s like dumping a jar of horseradish on a mayonnaise sandwich. His material is a barrage of violent psychosexual imagery and, once he secures a gay Mongolian-American assistant named Lloyd (Rex Lee), peppered with racist, homophobic asides. When he’s not verbally abusing the person standing closest to him, he’s breaking office equipment.   

Ari, Ari, Ari. What are we to make of him? 

He belongs to a different universe than the pussy posse, and the show’s most horrifying project is to slowly bring him into alignment with their balanced, good-natured fraternal energy. The Ari Gold of Season One is a black hole of narcissism and greed, spitting venom at the slightest touch, stuck in a vortex of his own bullshit. There’s a deft reversal in casting your heaviest acting talent as the power-mad agent, and it’s no wonder his riffing rage carried Entourage for so long — ugly as it is, Piven doesn’t miss a step; his unvarnished hostility is in many ways preferable to the casual sexism and low-stakes ball-busting of the boys. In a darker series, it could’ve been hailed as a searing indictment of Hollywood’s cruel, exploitative, soulless talent systems. Instead, Ari is handed the trajectory of a workaholic who must find his way back to his wife and family, and by the series finale, he’s a soft-hearted father figure to the lads as well. 

So much for the asshole Piven was born to play. “Hug it out, bitch.”

A number of sexual misconduct accusations against Piven amid the #MeToo movement have added to the sense that Entourage celebrated a toxic, misogynist culture. If hot women appearing solely as Bob Saget’s arm candy weren’t enough, the show also had a recurring character based on Harvey Weinstein — he threatens to ruin careers, although, notably, never the career of a woman refusing his foul advances. Then there’s the fact that the Entourage premise loosely derives from the backstory of executive producer Mark Wahlberg and his buddies, omitting their  possible criminal activity and Wahlberg’s disturbing record of racist hate crimes

With the smallest dose of hindsight, the series’ modest bright spots, and its comfort in vacuous luxury, are worse than soured. When finally gathering the fortitude to weather 2015’s Entourage movie, an ill-advised coda for a franchise running on fumes years prior, I needed a joint, a painkiller and several drinks to take the plunge, and glimpsing “Steve Mnuchin” in the producer credits didn’t faze me. Nothing had changed aside from Turtle losing weight. The entire thing hinged on Vince hooking up with Emily Ratajkowski. There were cameos by Piers Morgan and Matt Lauer.

It felt additionally perverse to binge the show during a global pandemic that has killed hundreds of thousands, and to submit to the vapid, lazy film as civil unrest grew in response to the murder of another Black man by police. I could sense my regression into the warm and enveloping stupidity of douchebags taking tequila shots and recalling the various asses they’ve tapped. In last scene of the dreadful movie, when the gang came up with the pitch for Entourage, the circle jerk was at last complete, my soul released to someplace beneath the frozen lake at the bottom of hell. I understood, then, the nihilism of Ari Gold — the early Ari, I mean — and his quest for domination without purpose or gain. For the agent, reality is a cycle, and it doesn’t reach a resolution; it rolls over and begins anew. The agent feeds on that steady churn.           

Does history repeat in like fashion, ever sustaining the parasites and hangers-on? 

I can’t say that Entourage — an unwitting parable of how many can live off the grossly inflated fortune of a single American aristocrat — suggests otherwise. Having spent some years in and around Hollywood, if not the business of it, I also realize that the series is hardly an exaggeration: White men get the money and jobs, they objectify and traumatize women and they claim the credit if anything goes well (or spread the blame if it doesn’t). At moments, noticing the familiar and favorite landmarks incorporated into the milieu of Entourage, some just a few blocks from where I sit now, I was stung by resentment: Vince, E, Drama, Turtle and Ari were tainting this city, my adoptive home, with their sleazy little quips and exploits. They were trying to take it from me, and I grew jealous, not of the hedonism and VIP rooms, but because they had arrived here first.

But I’m probably looking at it upside-down. My distance from the infernal engine of Hollywood is part of what allows me to romanticize L.A., and the industry was a nightmare long before Entourage replicated its issues by, uh, “spoofing” them. To take the sunnier view (and in Southern California, why not?) I’m glad I faced the city’s demons, and relieved that even by the standards of disposable viewing, this garbage is no longer acceptable. 

It’s become an artifact of the too-recent past, a case study in what you could “get away with” and why that stuff wasn’t ever worth saving. It memorializes the supreme, indifferent rot of this country in the years that followed 9/11, the Middle East wars and the rise of the surveillance state. No morals, no cool, no vision, no effort not to phone it in. I chuckled whenever the dudes had to scrounge for pot from an actual drug dealer. What a joke! How did any of us — how did I — endure the humiliation of existing in the U.S. in 2006? 

I can’t recall, I’ve blocked it out and I’m sure that the mind-altering events of 2020 have triggered similar, instinctual modes of self-preservation. At least we’ve mainstreamed socialism and firing sexual harassers, kind of.

Entourage wasn’t meant as brilliant commentary, or to challenge its audience. In aiming its sights so low, it curdled fast, obsolete halfway through. My advice, should you still want to dive in for some reason, is to imagine yourself dumb and happy, the idiot of the century. 

And remember, despite everything, you have won a great victory: That isn’t you on the screen.