Entourage, Insiders and the Death of Cool


In my younger and more vulnerable days – when I still thought fedoras were cool and would unironically quote Gatsby – I was a big fan of Entourage.

For someone who aspired to work in the film industry, but who was a bit too fat and ugly, Entourage offered something concrete to aspire towards. So you’re chubby? So is Turtle! So you’re short? So is E! So you’re talentless? So is Drama!

But, beyond that, Entourage was always about something that transcended simple wish fulfilment. Since the release of the Entourage movie, the stars have been repeatedly forced to defend its rampant misogyny and pornographic consumerism, and their default stance has been ‘it’s a male fantasy’. In that version of reality, the ‘male fantasy’ is cars, boobs and tequila; a sort of topless Cinderella parable where, instead of getting to go to the ball, you and your buddies get to snort coke off a swimwear model’s back.

Contrary to what Jeremy Piven and Adrian Grenier have recently said, Entourage (the TV show) was never really about the idea of a ‘male fantasy’. The pitch for a ‘male fantasy’, as they perceived it, was simpler even than the reality of Entourage. No, Entourage was all about being an insider.

We’ve all been seduced by Hollywood. It’s the reason we go to the movies, the reason Ronald Reagan became President, and the reason hundreds of Buzzfeed staffers have jobs. Doug Ellin, the creator of Entourage, knew just that: he knew we had all been deflowered by a nebulous concept that we had never encountered and were never likely to.

But when Entourage first arrived on the HBO schedule, it was genuinely running against the grain. If you think back to a movie like Robert Altman’s The Player (which the Entourage movie owes a huge, shuddering debt of gratitude to), the cliquey nature of subterranean Hollywood was sort of repulsive. The satire of The Player was in the fact that all these beautiful people were living beautiful lives, whilst, at the same time, exposing themselves as hideously vampiric nobodies. The Player intentionally undermined the public’s perception of there being a celebrity uberclass, for the sake of creating a gothic pantomime.

There’s a part of me that wishes I could say the same about the Entourage movie, but times have changed. And I blame Taylor Swift.


A few years ago, Hedwig wouldn’t have given two hoots about which celebrities were friends with which celebrities. It was taken as a sort of given that regular colleagues – say, Vince Vaughn and Owen Wilson, or Tina Fey and Amy Poehler – were on good terms. They probably eat Thanksgiving together, we thought, feeding each other turkey from solid gold forks.

And, even when we were aware of a genuine celebrity friendship, you had to be particularly bored and lonely to expend any energy thinking about it. And that’s because the cornerstone of celebrity is a sense of mystique, an almost otherworldly sense that they’re better than you and me in all sorts of unfathomable ways. Celebrity culture has long been predicated on not being able to imagine celebrities using the toilet, or buying bleach, or crying when the dog dies in Downton Abbey.

Celebrity was all about being an outsider. Some icons, like James Dean and Marlon Brando, defined their sense of ‘cool’ by rejecting societal norms (except in terms of culture, money and beauty), whilst others were outsiders simply because they were so far away from anything we could relate to. Try relating to Cher, it’s really hard.

But then Taylor Swift comes along and despite being more talented, more beautiful and more successful than you or anyone you know, she’s created a new mystique based on the idea that engaging with her work acts as a portal into the perfect universe of her New York clique. If you buy into the Taylor Swift mythology, and all that comes with it, you are doing so in order to receive an express ticket into the interior of celebrity culture.

There’s a moment in the Entourage movie where David Spade (just one of a billion unnecessary cameos) makes a joke (in as much as anything in Entourage is ever definable as a joke) about his movie opening on May 4th, against the new Hunger Games film. This joke’s target audience is, essentially, the 0.0001% of Americans who work in top-level film financing. So what’s it doing in a popular, mainstream movie? It’s there because we’ve culturally moved to a place where understanding a joke about top-level film financing is enough to give a sniff of a world where you’re there. If you get the joke, if you understand the context, then you’re in the Bentley with Vince, Ari, Turtle, Drama and E; you’re eating cupcakes with Taylor, Karlie, Martha, Selena and Zendaya.

The outside has been inverted. Doug Ellin was one of the first people to realise that, so, when it started, Entourage felt both aspirational and voyeuristic, giving a nuanceless insider portrait of Hollywood, that star-spangled nirvana we read about in magazines. Since it started in 2004, the refashioning of ‘cool’ has continued apace, which makes Entourage look both more prescient and more dated (not to mention the fact that its sexual politics were looking primitive prior to the arrival of homo erectus).

It’s much harder to be truly ‘cool’ now, because, to be cool, you need to be part of the group, and how’s an uncool loser like me ever going to be part of the group? Things were easier when all you had to do was walk the streets at night with a Walkman and a camo jacket, not living by society’s rules. Modern coolness is more complex and impenetrable, and circling away on an unstoppably rarefied spiral.

And, at the centre of the vortex, is Taylor Swift, a cat and utter nothingness.

Follow Nick on Twitter @nickfthilton

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