‘Entourage’ Is for the Girls

My friend Callie was having a bad day. She texted me that she was stressed with job stuff, feeling down on herself, tucking herself into a corner of a New York City street to eat a turkey hero alone. 

A few days before, I’d started rewatching Entourage, the HBO show from the early 2000s about a movie star and his three friends from Queens living their lives and bangin’ chicks in Los Angeles. I mentioned this to Callie and she said that she immediately felt happier just thinking about it. She went home to start a rewatch. Her third or fourth. 

I have also seen Entourage at least three times—all eight seasons, plus the 2015 movie at least twice. 

For years I’ve been curious about my deep love for the show. I am trans. I care about stuff like sexism, transphobia, the way women are represented on screen. I should find the show repulsive. It’s about four grown-ass men who act like teenage boys, who treat women as objects, who sit around and smoke weed all day. In its 96 episodes, I do not think it passes the Bechdel Test once. There are probably a total of five scenes where women are doing something other than fawning over, or being angry at, The Boys (and when they’re angry, it’s always because boys will be boys, and women never want them to have fun). 

And yet, it is the show that brings me the most joy of any show I’ve ever seen. Anytime I am depressed, I turn it on. And just hearing that annoying theme song, I feel a sense of relief, like I’ve entered a warm bath, or taken half a Xanny and a low-dose edible (legal disclaimer: don’t do this). 

I once wondered if my love for the show involved some amount of self-hatred, a television-based form of self-flagellation. But now I think I was asking the wrong question. The reason I like Entourage is simple: it’s about something I will never, ever experience in my life—being not only a man, but a really, really lucky and hot and rich one. 

I enjoy Entourage not despite it being a male-centered-fantasy-on-steroids, but precisely because it is one. In an era where seemingly every piece of media is algorithmically catered toward one’s identity demographic (this show is for women, this show is for the gays, this show is for 30-something coastal elites who have anxiety, this show is for conservatives who love cops), Entourage provides me with access to a world that isn’t meant for me. Watching it is the closest I’ll ever get to understanding what it’s like to be One of the Boys.

As the writer Virginia Heffernan wrote in the New York Times in 2007, during the series’ third season, it’s a show about, “how men love men, and how they hate themselves for loving men, and how they worry about loving men, and how they need to stand up to men so they can love women, or stand up to women so they can love men.”

Or, as Johnny Alves, the real-life person the character Johnny Drama is based on, puts it in an Entourage retrospective: “They call it ‘The Entourage’ but it’s just five boys who love each other very much.” 

Its dreamworld maleness helps explain why most of the people I know who love Entourage are women. It’s also no coincidence that Entourage was largely the creation of a woman, Ally Musika, who wrote “every other word.”

Entourage is not a male fantasy in the sense that most men aspire to be like its characters. It’s a fantasy about men. About what they’re like. About what they can be. And, I think, that’s what TV does at its best—not representation, not education, but fantasy.

It’s fascinating to watch the reputation of Entourage slowly crumble over the years. In 2004, when it first came out—as Vincent Chase becomes a movie star and his three very-New-York-City friends tag along with him to Los Angeles—the media largely liked the show. The first season has a 73 percent on Rotten Tomatoes. Alessandra Stanley at the New York Times called it smart, original, amusing. By season 8, the critical consensus had dropped to 46 percent. In 2015, the Entourage movie garnered a 33 percent, with Eric Thurm in Slate summing up the consensus as a, “​​vast, unceasing stream of critical urine that has continued to soak the dirt of Entourage’s grave.”

As Thurm points out, what had changed in those 11 years was not really the show (though it did run out of steam a little bit, as most shows that last that long do), but the world around it: people were getting sick of seeing primarily white, rich men on screen… “These, after all, are the people who are, if not responsible for much of the problems the world faces, at least the ones who unthinkingly benefit the most from it,” Thurm wrote. 

Thurm is partially right. Even 10 years ago, TV was much whiter, had fewer women, and barely any gay or trans characters (and trans people still are barely represented on-screen). People were aching for something new—they wanted to see other people, other lives, on screen.

But how Hollywood responded to this lack involved a misunderstanding of what people like about television. In its largely successful attempt to diversify the industry, the shows the industry produced became more serious and sanctimonious—kind of a downer. When we get shows about trans people now, they’re about how difficult it is to be trans. When we get shows with People of Color, they’re largely about racism. In heeding the call for diversity, the powers-that-be forgot that the best part of television is that it’s an escapist medium. You watch not to learn, but to forget. 

“The reason I like Entourage is because there’s never actually any problems in it—they’re going to go party, get some pussy, and Vince is gonna become the biggest star ever,” my friend Callie Zucker, who is a woman, and who started watching the show when she was about 15, said. “When I was a kid, me and my sister would play with stuffed animals and I’d always ask if we could play a scenario where nothing bad happened, where the animals just got along and got to go to a water park. Entourage is kinda that. They’re all just going to the water park together.” 

To Callie, calling it sexist misses the entire point. “Yeah, of course it is. I’m not arguing that it’s not,” she said. “I’m arguing that it doesn’t matter. I don’t want to watch a show where someone gets laid by being super respectful.”

That’s the problem with many shows today—few can be as fun as Entourage because everything is trying to be too respectful and educational, assuming that what women, trans people, or any demographic traditionally left off-screen wants is to hear how bad we’ve been treated and how miserable our lives are, even if they’re filled with inspirational beauty. We end up with boring content that does not allow us to escape, because it is no one’s fantasy for a man to prove how un-sexist he is before he flirts with a woman; it’s no one’s fantasy to watch someone explain why wealth hoarding is bad as they party in their mansion. 

That doesn’t mean TV or movies should stay away from those issues. But there should be room for both: content that really focuses on and elucidates racism, sexism, classism, and content that allows us to get the fuck away from all that. As of now, we largely have an uncomfortable and unenjoyable mishmash of both.

My friend April Clark, a comedian, and also a woman, puts it more succinctly: “It’s a show about what it’s like to be awesome,” she said. “Everyone wants to feel awesome, especially people who aren’t already always feeling awesome.” 

In other words, everyone, and especially those who don’t have access to universal acclaim, lots of money, a life unencumbered by sexism or racism, loves to think about what it would be like to have those things. 

My token male friend, Keyvan Shafiei told me this fantasy is what attracts him to the show too: it’s not so much the male fantasy of having lots of bitches, it’s the male fantasy of having lots of male friends who really love you.

“Vinny loved his friends back just as selflessly as they loved him,” he said. “He prioritized art above avarice. He was loyal. And he never obfuscated his roots or his love of family. He was packaged as the perfect man, not to mention that his ethnic ambiguity made him especially appealing to people like me—was he brown or just really tan?”

Which is not to say that we can only fantasize about those things through the lens of men. But there simply isn’t a show about other people that allows for that fantasy. Entourage’s closest female-centric parallel, Sex and the City, is of course partially a female fantasy, but the men in the show are full-fledged (or maybe half-fledged) characters, not objects, the four women get sad, they learn lessons. When the ladies return in the recent reboot And Just Like That, the fantasy is even further sedated—they’re now grappling with what it means to be conscious of social justice and learning what a nonbinary person is. That doesn’t mean the show is bad, it just means it doesn’t scratch the same itch as Entourage.

And that’s perhaps what I find most objectionable about Entourage—not the show itself, but that a female or trans or queer version of it hasn’t really been allowed to exist. People who aren’t white, cis men aren’t allowed to have fun and learn nothing on screen to the same degree. We must always be reflecting, taking things seriously, and educating our audience. The idea that women, trans people, whoever, can’t be as stupid, as objectifying, as crass and materialistic as the boys in Entourage, is to me the most sexist thing of all. 

If we’re reevaluating Entourage, I hope the lesson we learn isn’t that the show needed to be smarter. I hope it’s that we all deserve to be allowed to be as dumb.