I used to watch—and loudly espouse my watching of—the HBO series Entourage. I always found this to be an enticing, attractive element of my media diet as a bored, stoned teenager. I spent many late nights up with Vince, Drama, E, and Turtle, as they cruised Hollywood in search of a good time. But recently, I’m taking stock of the aspects of culture that piqued my interest as my understanding of gender and sexuality was shaped. 

Men in Crisis: Revisiting Entourage

by Katy D’Avella

Shamed by the plight of the difficult woman, a younger me sought clarity—or perspective—in the male gaze. Critic Emily Nussbaum wrote about the ways in which the HBO series Sex and the City was brandished as inferior because of its feminine, stylized nature. Its antiheroines were actually fun to watch—how embarrassing. So perhaps I examined the Entourage narrative as a blueprint for understanding masculinity. And perhaps it informed my own subjectivity. 

Men look at women. Women watch themselves being looked at, said John Berger.

Now, more than a decade later, I’m rewatching my old favourite show. I’m reliving the painful moments of misogyny, homophobia, racism, and more. It’s safe to say that the series did not age well. At times, a viewing session might feel a bit like traversing a warzone: at any moment, a landmine of sexual violence or transphobia might erupt, leaving me reeling.

But what started as a nostalgic hate-watch unfurled into something far more meaningful. Gliding from episode to episode, trapped in what John Semley called “televisual Stockholm syndrome,” I felt strangely intrigued, then endeared, and then began to ask new questions.

You’re not hot enough

The intro credits of Entourage seem to whisper-sing the thesis of the series: I wanna be your superhero, even if I tumble and fall. 

This of course is the now ubiquitous “Superhero” by Jane’s Addiction. As the song plays, our superheroes—the entourage—drive together in a flashy low-top convertible. I won’t sink so low as to associate their shared vehicle with a single, protruding phallus, but perhaps you will.

The opening scene offers up a version of Los Angeles that has never existed. Nelly plays as a crowd of thin, gorgeous women mill about in the sunshine. Our protagonists wander through a sea of unbearable whiteness to their lunchtime rendezvous. 

“The opening scene offers up a version of Los Angeles that has never existed.”

After the men celebrate the exit of an ex-girlfriend (“she’s a bitch!”), an evocative scene occurs. It’s the only moment in the 28-minute pilot where women have lines. Turtle, the driver of the group, lures the attention of two attractive women passing their table. The unnamed women ask why they’ve not been invited to a party. “‘Cause you’re not hot enough!” yells Turtle. 

As the episode rolls on, women continue to be portrayed as a monolith: thin, white, straight, and most clearly, as loathsome yet coveted objects of distraction. It’s notable even from so early on in Entourage that women are not viewed as truly desirable. Romance, or even erotics, are not an aim for our men. No, they seem to be tallying scores, attempting to amass sexual capital as sport. “I’m on ass patrol tonight,” brags Turtle. 

I am not interested in analyzing the one-dimensional nature of women in Entourage—about how Ari’s wife, a main character in the series, is never given a name. Surely, this has been discussed at length elsewhere. But the statistics are notable: in the series’s 96-episode run, women speak to other women nine times. 

We only have one rule

In the world of Entourage, home and family are re-imagined around groups of cis-heterosexual men who live, work, and party together. Vince, Drama, E, and Turtle live together in the Hollywood Hills. Much ado is made over of their shared homelife—from daily meals to house-hunting. 

There is a marked disinterest in the production of the classic nuclear family: marriage, kids, whatever. Early on, Turtle decrees the rule: “no girlfriends, no commitment”. 

Rather, the entourage becomes the nuclear family. And this family is centered around commitment and care. Drama cooks breakfast for the boys a staggering 29 times in the series. From Belgian waffles with fruit salad to tofu spirulina scramble, he cooks for his loved ones with all the care and pride of an Italian nonna. Meanwhile, Eric is scorned for moving into the guest house in search of privacy. And Vince is ferried around from place to place like a kid not yet old enough to have a license. 

Together, the men seem to both uphold and subvert the core tenants of heterosexuality. The minutiae of their daily lives is centered around rituals of courtship and mating. Yet emotional intimacy, responsibility, and homelife are reserved for each other. The brief appearances of women seem to act only as a conduit to reinforce the male bond. Who could forget the Mandy Moore story arc, when her and Vince’s tumultuous romance is resolved only by a friend intervention. Judith Butler might suggest that kinship is always already heterosexual—that what cements the feeling of family has everything to do with traditional practices like marriage and child-making. So when did it become admirable for a bunch of men to never settle down? 

Just as the women of Sex and the City challenged norms around family and intimacy, so too do the men of Entourage. For both quartets, happiness lies in resisting the urge to build a new family, and rather, depending on each other. Well, mostly.

Crossing swords

One of the most enduring soundbites from Entourage is the scream of ever-aggressive agent Ari Gold for his assistant, Lloyd. “LLOYD!” he shouts from his office whenever a problem arises. “LLOYD!” he bellows in any moment of professional weakness. 

Lloyd, the Asian-American assistant played by Rex Lee, is positioned in the series as a provocative counter to the otherwise overwhelming traditional masculinity. Visibly queer and utterly unpreoccupied with performing success and strength, Lloyd acts as a foil to the men of the entourage. In fact, he seems to be the only character in the series who is truly comfortable with his sexuality and gender.

However, or perhaps due to this, Lloyd is the frequent subject of homophobic slurs. His boss Ari flings insults about his sexuality and gender—often laced with racist affronts—in almost every episode. From his clothes (“like Michelle Kwan in drag”) to his car (“a prop car from Fast and the Furious”), mocking Lloyd’s queerness becomes the series’ most recurring quip. 

In fact, resisting homosexuality is a core motif in Entourage. Early on, Vince nearly refuses to act in a film where he would “play gay”. Turns out, it was a joke. And in the iconic “The Sundance Kids” episode, Drama and Turtle bemoan a shared sexual encounter with a woman. Rather than savouring the pleasures of the experience, they agonize over the vaguely homosexual nature of it, suggesting with disgust that they “crossed swords”. 

Again and again, and often through a mixture of humour and scorn, the men seek to construct themselves in opposition to queerness. In doing so, they pitifully attempt to mark themselves as strong and appealing to women. 

Was this funny in 2005? Or were these jokes dripping with irony as they exposed the insecurities of our protagonists? The more I watched, the more I wondered how much of Entourage was actually satire. Turns out, there are whole fan theories dedicated to this suspicion.

There’s a certain cognitive dissonance that comes with watching four straight men comically avoid being depicted as gay—whilst cultivating a family together. And spending so much time observing and discussing each others’ bodies. Surely Drama’s deep-seated obsession with male calves, and desire for calf implants himself, was a humorous nod to the pressures men faced to look and act a certain way in the early 2000s. So did the series have something to signal about the oppressive state of masculinity for all genders?

“Again and again, and often through a mixture of humour and scorn, the men seek to construct themselves in opposition to queerness.”

In rewatching Entourage, I’m still not sure. But one thing is clear. The series plays out like an allegory, where men duke it out to avoid weakness and ultimately, like the theme song says, to be the superhero. 

Now, I know who the real hero is. It’s not Vince, who dines on the riches of his Aquaman franchise. It’s not E, who gets the girl. And it’s not Ari, who falls from grace and climbs back up to the top. 

It’s Lloyd, who is confident, nuanced, and comfortable. Who sees his boss Ari’s flaws and vulnerabilities, and, like this audience, is strangely intrigued anyway.

Katy D’Avella is a writer based in London, UK.