The douchebag factor: Why the ‘Entourage’ movie is bound to fail

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Not matter what happens in the Entourage movie, we know they'll be walking

Not matter what happens in the Entourage movie, we know they’ll be walking

As you may have heard, the movie adaptation of ‘Entourage’ will be upon us soon, with a June 5 release scheduled. I haven’t seen it- I don’t think it’s been screened for anyone as of yet- but I’m a bit skeptical of the project’s success, for quite a few reasons.

No, it’s not just the relative lack of post-HBO star wattage of the main foursome- of the four, Jerry Ferrera’s part as the sixth banana in the “Think Like a Man” franchise has been the lone bit of box office success, with the guy playing the “movie superstar,” Adrian Grenier, not appearing in a single project that I can name since 2011.

It’s not just that the series has been off the air for four years, but feels like it’s been gone twice as long as that. Or that I can think of about 15 different defunct HBO shows more deserving of a movie adaptation (starting, of course, with Deadwood) than this one. Or that both “Sex and the City” movies were considerably worse than the very worst of the TV series.

Here’s why the ‘Entourage’ movie won’t work: Its primary ethos as a series, from beginning to end, entailed a level of douchebaggery that’s frankly a lot more frowned upon by our culture today than it was when the show debuted on HBO in 2004.

In case you’re not familiar: ‘Entourage‘ ran on HBO for eight seasons, which was longer than contemporaries The Sopranos, The Wire, Deadwood, Six Feet Under or Sex and the City. Loosely based on the life story of series executive producer Mark Wahlberg, Entourage concerned the Hollywood adventures of Vincent Chase (Adrian Grenier), a rising young movie star from Queens living the life of dreams in Hollywood.

In those he was joined by his friends from back in Queens, including his brother/has-been actor Johnny Drama (Kevin Dillon), business manager E (Kevin Connolly) and driver/aspiring music producer/limo impresario Turtle (Jerry Ferrara.) The fifth major character was Ari (Jeremy Piven), a loud, profane Hollywood super-agent.

The series was known primarily for projecting a glitzy, party-intensive version of Hollywood in the aughts- pool parties, movie shoots, and hundreds upon hundreds of scantily-clad women. There was also a very specific, generally accurate portrayal of loud-mouth East Coast male friendship, consisting of nearly non-stop insults and constant ribbing.

The show also focused on the business side of movies, tracing the various ups and downs of Vince’s career, including various movies (biopics of Ernesto Ferrari and Pablo Escobar, adaptation of “Aquaman”) that have since been developed as film projects in real life.

The ‘Entourage’ series got off to a decent start, but it sadly ran out of interesting ideas about midway through season 2, falling back from that point forward on the same handful of lazy storytelling crutches: Non-stop celebrity cameos, pie-in-the-sky wish fulfillment and, worst of all, the habit of solving every plot dilemma with a laughable deus ex machina.

Vince and the gang can’t get to Cannes on time? Hey, here’s Kanye West with a private jet. Vince’s career looks like it’s over? Here’s Martin Scorsese on the phone with an offer for a blockbuster movie. There were never any stakes to anything, because we always knew some perfect, totally unearned solution would fall out right out of the sky to save the heroes and allow them to continue being rich and famous.

My favorite reaction to this was critic Dan Fienberg and Alan Sepinwall’s prediction of the series finale, delivered on their podcast at the time, that they all drive off a cliff, but the car has a parachute and fire extinguisher system, and then at the bottom of the cliff is a million dollars, on a yacht with porn stars, and Steven Spielberg, who immediately offers Vince the lead role in his adaptation of the Bible.

Entourage was pretty clearly a subject of mockery by 2009, as evidenced by this spot-on College Humor parody (with Adam Pally as Vince, Thomas Middleditch as E and Bobby Moynihan as Turtle):

But even worse than the weakness of the structure and writing? These guys were just, for lack of a better word, douchebags. See this list of ‘Entourage’s douchiest moments, that Uproxx put together around the time it went off the air; it’s by no means an exhaustive list.

And this is what brings about skepticism about the series’ return. Bad as all of this looked when it was first airing, the way large segments of audiences engage with pop culture has changed a lot in the last decade- and not in a way that does the legacy of ‘Entourage’ any favors.

Annnoying and reductive as “problematic”-mania can be, the fact remains that if a work of art does something that’s sexist or racist or otherwise insulting, they’re going to get called out on it in a way that wasn’t an issue a decade ago- and for the most part, that’s a good thing.

People complain about “sexposition” on Game of Thrones? That Silicon Valley doesn’t give enough depth or prominence to its female characters? Entourage was more guilty of those sins by a factor of thousands. And the sort of antics the show could get away with during most of its run just don’t fly anymore. “Bro” didn’t used to be an insult.

Remember the way this show treated women, and the way the guys talked about them? There’s no denying that with a handful of exceptions, female characters had few functions in the ‘Entourage’ universe other than disrobing before the male characters.

The character of Ari Gold- a raging asshole and misogynist who, among other sins, shouted racial and homophobic slurs at his assistant Lloyd in just about every episode- was portrayed as sympathetic and even at times lovable. That’s not something that would fly so easily today.

Remember the episode where guest star Stephen Tobolowsky accidentally hooks up with a trans woman? Or the episode where Vince’s friend from rehab (played by Tig from ‘Sons of Anarchy’) shot himself dead in a bathroom, and minutes later the characters were chasing each other around with a dildo?

So now we have the Entourage movie, which essentially has two choices: Be exactly like the show, and embrace all of its awful aspects in total, or be nothing like the show, and send its audience home unsatisfied and unhappy.

For all I know the ‘Entourage’ movie will find some way to acknowledge the passage of time and the aging of the characters, and even do so in a way that’s compelling, enjoyable and funny. But please. There’s parties and bikini girls and out-of-nowhere triumphant endings to be had.

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  • Cesare di Angelo

    To paraphrase Ari Gold Stephen Stiles has so much cum in his eyes he’s not only unable to recognize satire but is clueless to what a balless emasculated pussy he is or realize how the feminization of the workplace has taken all the fun out of it. Going to work is shittier than ever and fantasy escape of wish fulfillment and boobs is just the prescription. Who wouldn’t like to talk so energizingly to the c*nt in HR in an all out battle of the sexes unconstrained by sexual harassment lawsuits meant only to take testosterone out of work and life. Nor does he understand the fomenting cultural backlash against the pc crap that seeps from the progressive left ‘s wimpy vision of utopia where all women are believed despite being lying liars If Mr Stiles, and I do use the word Mr. skeptically, understands the etymology of the word douchebag, he would understand how it must unreservedly be applied to his prissy candied ass self suffering as he is from penis envy.
    I predict a great success for the film just as a response to the these new prudes.

    • Joe Gillis

      Wow, Cesare. If you meant for this comment to be performance art, I would give you a thousand likes. If not, enjoy your stupid movie, douchebag!

      • Cesare di Angelo

        Thanks for the thousand likes Joe, and as a fellow traveler in appreciating the known value of ad hominem argumentation I salute you even though some of your other comments are douchey.worthy.
        There are plenty of reasons to dislike Entourage that Stiles barely glances upon. He essentially misses the whole point because of his political blinders. I don’t know if it’s saying much but unlike Stiles you ,like pretty much everyone else ,understand the outrageous which is the essence of the comedic in this series.
        But the truth in jest still is a warning of the emasculation of men in a misbegotten strategy.