Entourage’s legacy was more complicated than just money and sexism

Has any hit TV series aged quite so radioactively as Entourage? The eight-season HBO sitcom, which centres on fictional Hollywood A-lister Vincent Chase (Adrian Grenier) and his circle of cronies, reps, and hangers-on, has become synonymous with a certain brand of maleness. To its detractors, Entourage is basically “Toxic Masculinity: The Show” – with a fanatical worship of wealth, womanising and celebrity culture thrown in for good measure. Outing oneself as an Entourage fan in this day and age is, in other words, quite the red flag.

Based loosely on the life – or, rather, the lifestyle – of Mark Wahlberg (minus the history of racist hate crimes), Entourage was never quite a phenomenon. At the time HBO started airing the series, 20 years ago today, the US network was in the midst of a historic purple patch. Entourage overlapped with The Sopranos, Deadwood, Six Feet Under, Sex and the City, The Wire, and Curb Your Enthusiasm; compared to these shows, it was a crass and obnoxious interloper. Its reputation for misogyny has only snowballed in recent years, something not helped by sexual assault allegations lodged against ex-cast members Jeremy Piven, who played Vinnie’s foul-mouthed agent Ari Gold, and Kevin Connolly, who plays Vince’s best friend/manager Eric “E” Murphy.  (Both actors have denied the assault allegations.) That Entourage was deeply, transparently problematic is pretty much beyond dispute at this point. And yet, all these years later, it would be inaccurate to write off the series as merely an amalgam of its worst qualities.

Often, apologists for Entourage will defend it from the same banal parapet: the dubious assertion that it is really a show about male friendship. In truth, it has little of value or nuance to say on the subject. Far more interesting is how Entourage explores the movie business – frequently, with a kind of insider-y skew. The show became known for its panoply of A-list guest stars playing themselves. (Entourage did not, however, originate this trope – it came more than a decade after The Larry Sanders Show, an immeasurably smarter, funnier and classier inside-showbiz satire, set the precedent.) Beyond this gimmick, the series was generally astute in its understanding of the film industry and gave fans a fictionalised peep behind the scenes of, say, the difficulties of promoting a film on a talk show, or what it’s like to be in conflict with an ursine super-producer named, not-so-subtly, Harvey Weingard. More than this, though, Entourage touched upon something fundamental about the way we as a culture narrativise the film industry.

If you spend enough time immersed in moviegoing culture, you start to scrutinise things like career arcs, or the nagging “what ifs” that festoon the history of popular cinema. What if Stanley Kubrick had been able to make his Napoleon? What if Will Smith hadn’t turned down The Matrix? Entourage, set in a parallel universe in which Vince Chase is as much a household name as Matt Damon, allows us to live in this kind of hypothetical reality – a reality that also proved bizarrely prescient. We watch as a post-Titanic James Cameron casts Vinnie in an adaptation of Aquaman, years before Jason Momoa would actualise this IRL. We watch as Vinnie’s passion project, Pablo Escobar crime drama Medellin (not dissimilar to Netflix’s Narcos), becomes a career-threatening disaster. We watch as Vinnie bounces back – starring in Martin Scorsese’s Gatsby (a few years before Baz Luhrmann’s 2013 version), then Frank Darabont’s Ferrari (a decade before Michael Mann’s Ferrari). The fact that all the brief snippets of these fake films we see are comically, eye-wateringly dreadful barely matters.

On a very basic level, too, Entourage is a successful exercise in vicarious wish fulfilment. Watching a group of cushy rich people buy nice things and go to expensive places might not be traditionally compelling storytelling, but there is a kind of giddy kick in witnessing how life is lived at the upper end of the fame spectrum.

The first couple of seasons were warmly received – with caveats. “We can assume that it’s not a long way from real life, Hollywood-style,” wrote The Guardian in a review of season one. “Which is to say vacuous, mindless and utterly appealing.” As the series went on, however, there was a noted decline in quality. What was once playful and lavish had become leaden and indulgent. By the time of the final season, not to mention the theatrically released sequel film, any scintilla of credibility had evaporated. Co-starring Haley Joel Osment, Billy Bob Thornton and pro wrestler Ronda Rousey among others, the film Entourage (2015) sees Vince turn his hand to filmmaking, directing an adaptation of Dr Jekyll and Mr Hyde that’s set in a futuristic underground DJ scene. We are supposed to believe this movie is a masterpiece, when the small glimpse we get makes it seem like the worst deodorant advert ever recorded. It was terrible.

Criticisms of the show’s sexual and gender politics have been rife down the years. Wired’s Kevin McFarland wrote that the series was “a reliable font of crass humor and casual misogyny and homophobia”. Refinery29’s Anne Cohen wrote: “Most women on this show are objectified to the point of absurdity.” For all that these complaints are valid and true, it’s noteworthy that many of Entourage’s standout supporting characters – publicist Shauna, played by Goodfellas’ Debi Mazar; Ari’s wife Melissa (Perrey Reeves); Ari’s industry frenemies Barbara (Beverly D’Angelo) and Dana (Constance Zimmer) – are women. But this doesn’t exculpate anyone. (Mazar has in fact shed a damning light on her time on the show, telling PeopleTV: “[Series creator Doug Ellin] wrote a really strong character, but that set was very testosterone-driven and misogynistic.”)

In her 2011 memoir Bossypants, comedy maven Tina Fey describes watching the entire series of Entourage while using a breast pump. “Over the whir of the milking machine,” she wrote, “I could almost hear my baby being lovingly cared for in the other room while Turtle (Jerry Ferrara) yelled across an SUV: ‘Yo E, you ever f*** a girl while she has her period?’ I was able to do this for almost seven weeks before running out of Entourage episodes and sinking into a deep depression.”

This is, essentially, the series in a nutshell: crude, problematic, and not all that funny. And, of course, filled with SUVs. But I’ll be damned if I didn’t watch all of it.