Male Friendship Is the Ultimate Fantasy: The Existential Mind Games of 'Entourage'

Doug Ellin and I are eating lunch at Porta Via, a posh restaurant on Canon Drive, in the part of Beverly Hills where it's OK to call something "posh" without feeling all dickish about it. Ellin is the former showrunner of Entourage, as well as the guy who wrote and directed the Entourage movie, which opens in theaters today. I am the guy who just inadvertently caused mass outrage among a group of paparazzi by blocking in a large SUV that was trying to escape with some celebrity in it. Doug Ellin is here with his dog, a rambunctious six-month-old German shepherd named Baron. I am here with my glasses, which have been chewed on by my two-year-old Pomeranian/Shetland mix. He's eating a stir-fry. I'm eating a tuna-salad sandwich. We're talking about friendship.

"Men," he tells me, "become consumed with careers and money. A lot of people get into the Ferraris and that stuff, but the ultimate wish fulfillment of Entourage is that men can be with their best friends, enjoy themselves, and have some peace."

Male friendship, I offer, might be the ultimate fantasy.

Ellin agrees. "Everyone's always like, 'Is this really Hollywood?' I'm like, 'Yeah, it's real.' The most unreal thing is that it's actually hard for four guys who are thirty or thirty-five to maintain those relationships."

When Entourage made its debut, in 2004, it was unlike anything else on TV. Like Sex and the City, it featured a set of personality archetypes discussing the various minutiae of human male-female interactions in a backdrop of glamorous locations. Like The Wire, meanwhile, it offered a detailed, no-holds-barred look inside an industry whose infrastructure was often shrouded in mystique and misinformation. But unlike the universe of Carrie and her friends, Entourage was centered around men, and instead of laying the Baltimore criminal underworld out in painstaking detail, the show was about Hollywood.

The show was based around both Ellin's experiences as a writer and director and those of executive producer Mark Wahlberg, who in the early days of his stardom used to have a camera crew follow him and his rough-and-tumble Boston friends around.

"Almost everything" from the show, Ellin tells me, was based on real-life events. "A lot of it from my own life," he adds, citing a story arc in Entourage's fourth season in which Vince's brother, Johnny "Drama" Chase, tries to get his house re-zoned for a Beverly Hills zip code. It turns out that Ellin had actually tried just that. "I lived on North Beverly Drive. I was fifty feet away, and then the street would change." He explains that unlike Drama, whose reasons for getting a Beverly Hills zip code were purely rooted in vanity, Ellin had actual reasons to lobby for the switch. "Once you're in Beverly Hills you're in paradise," he says. "It'll give your house greater value and your street will be paved."

Most of the characters have at least a sliver of reality in them. Ellin told me that Billy Walsh, the intense, perfectionist filmmaker, is based on his friend Rob Weiss (who eventually helped write and produce the Entourage movie). The savvy, verbally abusive superagent Ari Gold is based on Ari Emanuel, whose brother Rahm served as Barack Obama's chief of staff and is now the mayor of Chicago.

The issue the Entourage movie faces, essentially, is that of stakes. Entourage is a show that thrived on a sense of foregone conclusions—the guys go to a place and do some stuff, people are impressed by Vince's fame, and then the boys banter. Ari screams at his assistant, Lloyd, and everybody calls it a day.

Entourage the film has to deal with the same problems that the 1979 Star Trek movie did. If you'll recall, the first Star Trek movie was way too concerned with the fact that all of the characters from the show were in the same room, doing the same sorts of stuff they were doing on the show. They were given a non-plot to resolve that ended up being a lost research satellite, and the movie sucked. With Entourage, the metaphorical lost research satellite appears to be the fact that star Vinnie Chase wants to direct a movie. Manager Eric, meanwhile, has a pregnant ex. The ne'er-do-well turned tequila mogul Turtle wants to have sex with an MMA fighter, and the perpetually put-upon Johnny Drama just wants to have someone acknowledge he exists.

Will Vince's film succeed? Will Eric and his ex get back together? Will Turtle land the pugilistic woman of his dreams? Will Drama fuck? Despite the fact that I haven't actually seen the movie, the answer to all of these questions is almost certainly "yes." In the world of Entourage, everything works out. (Assuming you are a member of the entourage.)

Before I moved to Los Angeles, I had never watched Entourage. Everyone I hated in college for being overly bro-y invariably loved it, which meant that in the interest of distancing myself from the scourge of bro-dom, I had to hate it. But when I moved to Los Angeles, I decided to mainline the entire series, watching multiple episodes per night and cramming the entire eight-season series into a few weeks. What I found was that I had been wrong. Entourage is amazing, and everyone who cares about anything should watch it.

The thing that enthralls me about Entourage is not the glitz. Nor am I invested in the process of how big-budget Hollywood films are made. And to be honest, I don't feel particularly connected to the characters. Instead, to me, Entourage is a mystery wrapped in an enigma wrapped in a mindfuck, blurring the lines between reality and unreality until you truly believe the distinction between the two doesn't exist. If, as Ellin instructs you to, you ignore the bells and whistles of wealth and status that accompany Entourage, the show's central conceit reveals itself: Four childhood friends have the same conversation, over and over, for eight years. It's like Waiting for Godot, but longer, and with more dick jokes. Because of its cyclical nature and extremely low stakes, Entourage is one of the most watchable pieces of entertainment ever created. Like an episode of Law and Order, the viewer can instinctively anticipate what's going to happen, and instead of being upset that it does happen, is given a mental reward in the form of a shot of a cool car or the guys engaging in some arch camaraderie when things work out the way we assume they will.

Ellin describes Entourage as "the exact opposite" of Robert Altman's Hollywood satire The Player. "This is what it is," he continues. "I like it. I embrace it." Later I will float the idea to him over email that Entourage might be postmodern. He responds, "I guess some could view the movie as skeptical about the business. I try to make it as realistic as I see it while hopefully still entertaining."

That assumed reality that Ellin strives for is exactly what makes Entourage, in its own way, such a radical piece of entertainment. The show doesn't ask that the viewer suspend their disbelief; it actively encourages the viewer to assume what they're watching is more or less real. Scott Vener, a close friend of Ellin's who served as the show's music supervisor and also worked on the film, told me, "All of the places [used in the show] are real—where they go have coffee, where they go to a nightclub. Every place that was named was a real place." Celebrities pepper the show as well. When Vince stars in Aquaman, it is directed by the real James Cameron and shatters Spider-Man's real box office record. You can watch these fake people interact with Bob Saget, Gary Busey, and Sasha Grey, and the show's structure ensures the viewer assumes that this is a slanted take on how these people really act. If we are to assume that one of the facets of postmodernism is that a work is aware of its status as a fabrication, then Entourage is using its proximity to reality to constantly draw attention to the line between fact and fiction, and coming out all the stranger for its efforts. That Ellin is seemingly unaware of this (or just genuinely doesn't care) suggests that humans in Hollywood themselves are themselves unreal, and by holding a mirror up to that reality Entourage is unwittingly exposing this.

The principals of Entourage are as follows: Vincent "Vinnie" Chase, the beautiful soft-hearted star who his friends must keep happy. Eric "E" Murphy, Vinnie's overly cautious manager. Johnny "Drama" Chase, Vince's older brother who wishes to reclaim the glory he once had as a cast member of a show called Viking Quest. Finally, there is Salvatore "Turtle" Assante, Vince's "driver" who mainly smokes weed and tries to cash in on his friend's fame.

These guys are rooted in reality as well. Vinnie is based on an amalgam of Wahlberg, Tobey MacGuire, and Leonardo DiCaprio. Kevin Dillon, who plays Johnny Drama, is the less-famous brother of Matt Dillon. Kevin Connoly, who plays E, was once a member of Leonardo DiCaprio's late 90s crew known as the " pussy posse," which means that if we are to believe Vince is indeed somewhat based on DiCaprio, Connoly is more qualified to play this role than anyone else in the universe.

Because we're meant to assume that Entourage takes place in a universe that is nearly identical to ours, we're also meant to assume that both universes share the same celebrities. This becomes existentially interesting in scenes such as the one where Bow Wow (playing a screenwriter) punches Seth Green (playing Seth Green) in the face. Are we meant to assume that Bow Wow's music does not exist in the Entourage universe, despite the fact that Saigon, a rapper who is significantly less famous than Bow Wow, plays himself in an arc where he's managed by Turtle?

As Entourage unfolds, these questions only pile up. Former child actor Haley Joel Osment plays one of the villains of the Entourage movie, as does Billy Bob Thornton—does this mean that in the world of Entourage, movies such as The Sixth Sense and Sling Blade never happened? But they must have happened, because in season four, Ari meets Sixth Sense director M. Night Shyamalan at a cemetery, and Ari tells his put-upon assistant, Lloyd, over the phone, "I see dead people." Do the characters who encounter Osment and Thornton in the movie ever think, Man, this guy sure does look like the creepy kid from that spooky Bruce Willis movie, or, Didn't this guy used to be married to Angelina Jolie? They must.

Just as Entourage imitates real life, every good Entourage scene imitates every other good Entourage scene. First, the boys are provided with some sort of stimulus. Then they banter. The banter is as follows:

Vinnie: I am famous, let's do something.
E: As your manager, I have concerns about this.
Turtle: Let's do it! I would like to leech off of Vince somehow.
Drama: I was once famous, and I have already done this thing (albeit in a somewhat pathetic manner).

The backdrops for these conversations rarely change. They are at a party, surrounded by beautiful women. They are at Urth Cafe, running into celebrities. They are in Vince's home, where they all live, and Johnny Drama is cooking everybody breakfast. They are at Ari's office, and Ari is yelling at Lloyd, and also them. And so on, and so forth, into a spiral of infinity.

As the show progresses the characters drift apart and somewhat come into their own ("They had to," Ellin tells me). Vince develops and loses a drug problem, Eric ends up owning a management company with a character played by Scott Caan (who is, confusingly enough, named "Scott"), Turtle goes to business school and becomes a tequila mogul, and Drama ends up starring in a Family Guy–esque animated series with Andrew Dice Clay. But no matter how high or low the boys soar, they return to this conversation format, usually at Urth, which serves as a joyous Greek chorus that reminds us we are in the fantasyland of Los Angeles and not some bullshit-ass podunk town where celebrities would never hang out in. No matter how dark the skies might seem for the crew, the clouds inevitably part and the sun of success shines upon our heroes.

"I love this place," Ellin tells me of Los Angeles, adding that he thinks Entourage is "one of the better-looking LA movies I've seen." Later, he will say, "A lot of people tell me they came to LA because of Entourage." He claims Tyler Thompson, who's producing the upcoming Tom Cruise vehicle Mena and in 2012 was named one of Forbes's 30 under 30 in the category of entertainment, was originally inspired by the show to come to Los Angeles.

If Entourage was a show about making movies and Entourage is a movie about making movies, it only makes sense that its actors, whose characters are far more famous than they are in real life, must now start portraying their characters in real life.

Indeed, the cast of the movie showed up to this year's Golden Globes in character to shoot for the film. Ari Gold, a fictional character, wrote a real book that you can buy with real money, and gave an interview to Matt Lauer in which he said "fuck" on national television, presumably incurring a real FCC fine. Kevin Dillon appeared on Jimmy Kimmel Live as his Entourage character Johnny Drama. At an Entourage press day, Adrian Grenier gave advice to the actor who's set to play Aquaman, despite having merely portrayed an actor who played Aquaman in a TV show. Jerry Ferrara, who plays Turtle, opened up a restaurant called Fat Sal's Deli, which, given Turtle's business school background, seems like something he would do.

Ellin tells me that the studio is already gearing up for a sequel, and Vince—er, Grenier—told the New York Times his goal for Entourage is for it to become "A franchise that hopefully will never die until one of us does."

If this happens, Doug Ellin will become an extremely rich man. Until then, it's time to pay for lunch, and he's just realized he's forgotten his wallet. Still, just like everything works out in the universe of Entourage, a deus ex machina falls from the sky and into Ellin's lap. Turns out his brother has a tab at the restaurant—Ellin tells the restaurant to charge him instead.

Drew Millard is on Twitter.