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Hugging it Out

A bicoastal e-mail debate on the end of Entourage

The eighth and final season of HBO’s Entourage premieres Sunday night, much to the delight of all people who love the worst things about Hollywood, male friendship, and cross-marketing tequila. Molly Lambert and Chuck Klosterman were able to preview the new season on opposite coasts and proceeded to conduct the following e-mail discussion, most of which makes only slightly more sense than that string of episodes featuring the rapper Saigon. But — as always — everything works out nicely in the end …


What the hell is going on with this show? It’s like it suddenly developed sentience. They are addressing within the show every criticism you might have ever lobbed at it, finally attempting to deepen the friendships between the guys and their relationships with women. I don’t know why, but I still care, I really do.

I’ve always loved Drama. He is a genuinely great fictional character, like a Shakespearean clown. I love the alliance between Drama and Turtle. They jockey for status, but then ultimately protect and don’t want to hurt each other. On The Sopranos it was a given that any of the crew, no matter how loyal, might turn on Tony if things got dire enough. On Entourage you get the sense that they really do care about preserving these friendships, because it’s not just business.

I don’t think I realized how much I had actually invested in the friendships until I saw How To Make It In America, which is exactly the same show but with totally boring characters and even lower stakes involving Kid Cudi and jeans. Granted “will Medellin bomb?” is pretty low stakes for a fictional universe, but if we’ve accepted that we want these guys to do well, it seems like they’re finally questioning (a) what “doing well” in Hollywood means, and (b) whether these guys actually deserve to do well. Which is also what Mad Men is really about.


The fact that you use the word “care” is interesting to me. I know that people who make television shows (and people who talk about television shows) are always obsessed with whether or not the audience can (or should) care about specific characters, but that barely seems relevant here. To me, this show is mostly about everything that surrounds these people — what L.A. looks like, what kind of cars they drive, what specific anxieties people in Los Angeles are assumed to be obsessed with, what kind of music a rich person would think a cool person might listen to, etc. The guys are just the mechanical parts that make it into a TV show, because you can’t have a TV show without people talking about themselves. I’m not sure how much people really “care” about Vinnie Chase. I think if Vinnie Chase had died from a drug overdose in the finale of last season, the public reaction would been, “Wow, Entourage is suddenly compelling.” I can’t imagine the person who would have said, “Damn, I’m really going to miss the dude.”

What I like about Entourage is that it defies the viewer to think about it as a fictional world. In the first episode of the new season, there’s a cameo by the star of a popular CBS sitcom, but this “star” is considered only mildly famous within the grand scheme of Hollywood. So there’s this fleeting moment when you don’t know if this person is playing himself, or he’s being introduced as a new character on Entourage. This type of weird sensation happens constantly. Whenever Vinnie is interested in a movie script, my immediate question is, “Does this sound like a movie that could actually exist? Is this the kind of career move a celebrity of Vinnie’s stature might make?” When Turtle pulls up alongside 50 Cent in his car, the only part of the interaction that’s intriguing is the degree to which that interaction actually resembles a random conversation between a famous rapper and the friend of a famous actor. To me, the reality of Turtle and Drama’s friendship is a secondary concern.

Here are some things I’d be interested to get your opinion on:

1. You live in Los Angeles. People in England seem to love Entourage (in 2006, The Guardian named it the best show on television). So let’s pretend you have a very rich, very attractive, incredibly ambitious friend living in London who’s never been to L.A., and she decides she wants to move there to get involved with the film industry. She asks you, “On a scale of 1 to 10, how much will my life be like Entourage“? What would you tell her?

2. Is E a good person?

3. If you were asked to write a script for this show, what would be the premise of the episode?


The most hilarious thing about this season and last is the idea that it would have taken Vince seven years of being an A-list (is Vince supposed to be A-list?) actor to develop a raging coke problem. And that the other dudes would care about his coke problem affecting his work and personal life, and not just be worried the money is going to run out. Vince is a non-thing. I’m never sure if we’re supposed to believe he’s a good actor. Do you think we are?

The aspect of Hollywood that was underplayed before but seems to be coming up now with Scott Caan’s character is how much everybody in entertainment is always bullshitting each other. And that if you are naive enough to trust all the people who are like, “Of course I’m going to make sure your comeback goes perfectly,” you will be surprised when they abandon you if your comeback fails.

Totally agree that the best thing about the show is when they have a famous person on and you’re not sure whether they’re meant to be playing themselves or a fictional version of themselves until they address them by name (like William Fichtner isn’t playing himself, but Andrew Dice Clay is).

I’ve never been very interested in the materialist aspects of Entourage, even though it’s always been the same fantasy about having a million cars and a million women (and that it equivocates those two things as being the same). I gave up on the show for a few seasons because I was tired of how much they always won. No matter what went wrong, nothing bad or depressing ever actually happened to them. Every episode ended with high fives and snowboarding. That got boring and also felt like the show was taking place on another planet.

It’s true that the reality of their friendships is always secondary to all the other bullshit on the show, but what I like about this season is it’s getting towards the idea that all they ultimately have is those friendships. They can’t afford to screw each other over, but they also don’t want to. I like that, for a show that is so superficial and portrays L.A. in a superficial way and emphasizes all of its worst aspects, it’s also about how lifelong friendships are not superficial, and how that is more complicated.

To answer your questions …

1. It depends what she’s trying to do. If she’s trying to be a cinematographer her life might be a 3 or 4 on the Entourage scale. If she’s trying to be an actress, more like a 10. Entourage is a pretty accurate reflection of agency culture, which does involve a lot of phone slamming, smoked glass, and beer pong. I don’t think I’ve ever seen them depict any of the boring bullshit that actually goes into moviemaking, but that’s not what the show is about.

2. E is not a good person. He is just surrounded by people who are even worse than he is. I buy that he’s smarter and more sensitive (sort of).

3. I did write a spec episode of Entourage! When I first moved back. I rewrote it a billion times and got a lot of advice from people, but nobody told me the actual cynical truth about the only surefire way to break into Hollywood, no matter how good you are at anything: You have to know somebody.

I’ll take this last moment to inform you that Entourage has 9 stars on IMDb.


It has always been my assumption that Vince is supposed to be a supercharismatic “eat the lens” type of performer who still has high-brow aspirations. I know he was modeled after Mark Walberg, but I initially though they were going for a Leo DiCaprio trajectory: Queens Boulevard being a composite Gilbert Grape/Basketball Diaries mainstream art house flick, followed by Aquaman (which is always portrayed as being some quasi-Titanic-level blockbuster), followed by Medellin (which is like what would have happened if The Beach had failed worse than it actually did), and then he somehow makes a Scorcese movie that everybody loves. Maybe not, though.

The fact that everything always works out for everybody on Entourage is probably the single biggest complaint people have with this show, and it’s ultimately the reason this program is ridiculous. But there’s almost no way around this. I mean, the show is directly called “entourage,” and failures don’t have entourages. This is intended as aspirational TV. I do think it would have been interesting if the makers of Entourage had decided to make this final season totally dark and weird, with every episode ending negatively until the finale (where Vince would be bankrupt and wrecked and forced to move back to New York). Because if they did this — and if the four core characters still remained friends, no differently than they were in the debut episode of Season 1 — it would sort of redefine the word “entourage” and suggest that this truly was a show about male friendship, and that the only difference between “having an entourage” and “having a group of friends” is how total strangers perceive your success. But now that I’ve seen the first three episodes of this season on DVD, it’s pretty clear this devolution is not going to happen. On a semirelated note, I was also surprised that the writers decided to initiate this final season by borrowing a central plot twist from midperiod Happy Days.

If you were about to meet a new person and all you knew about this individual was that “He/she is really, really into Entourage, what would that mean to you?


What’s the Happy Days plot twist? In TV writing it’s called a “Gilligan” when a character is like, “There’s no way I would ever do [X] thing,” and then it cuts to a shot of them doing it. Would Entourage be a different/better show with different actors playing Vince and Eric? Their friendship is the least interesting part, but it’s also the emotional anchor of the show that we’re supposed to invest in. Sex and the City was mostly an aspirational fantasy (replace endless cars and women with endless brunches and men) but as hypermaterialist as it is, it always came back to the idea that you care primarily about these four people staying friends with each other. But Sex and the City also consistently went darker and weirder than Entourage is willing to go. Which is why I really enjoyed the seventh-season finale of Entourage, because it was so dark and weird.

The main issue is that Entourage flat-out refuses to show the entertainment industry as anything other than glamorous. Superstardom may be glamorous, but most of filmmaking is just a job. Almost nobody is a superstar, and superstars don’t stay A-list for long unless they are genuinely talented in some way. And sometimes even the talented people get such big egos they blow it (Mickey Rourke). In 2001, HBO turned down the Judd Apatow pilot North Hollywood, which had a pre-stardom Seth Rogen and Jason Segel (and Amy Poehler) as struggling actors sharing an apartment in the valley. They picked up Entourage instead.

When people tell me they are big Entourage fans I ask them what their favorite episode was, and the answer is always either Gary Busey or the one with Val Kilmer as the Sherpa. And then I agree. Entourage is a fantasy show like True Blood or Game Of Thrones. It just takes place in an uncanny alternate world that looks like Los Angeles. It doesn’t actually exist.

So what’s your favorite episode?


I don’t want to give away the Happy Days twist — people will either recognize it immediately or have no idea what I’m referring to. I suppose it’s pretty pathetic that my fundamental TV references are now 33 years old, particularly when one of the main characters in the program we’re ostensibly discussing is only 22. As for my single favorite episode — I don’t know if I can even answer that question. I guess I don’t think about this show in an episodic way, although I’m not sure what the alternative way to think about Entourage would possibly be.

There really is something brilliant about the way Entourage is presented, though. It manages to feel like a much more “important” show than its content would justify. I feel like people will remember this series for a long time and continually use it as a cultural reference point, even if those memories and references are wrapped in condescension (in this way, it’s exactly like Sex and the City). Entourage is only 30 minutes long and used to come on right after The Sopranos, so it was immediately easy to watch; it constantly revolved around semi-arcane aspects of the entertainment industry, so people in the media loved writing about it. And as a result, it always seems to be part of the conversation when people think about modern entertainment.

It’s an easy show to criticize superficially, but difficult to criticize successfully — almost every negative thing about Entourage ultimately works in its favor. You can say it’s predictable and escapist, but there’s always a market for predictable escapism. People like those qualities, because it makes them feel secure. You can accuse it of being sexist, but — if a viewer disagrees with that specific accusation — that criticism has the paradoxical effect of making the viewer like it even more (because now the content strikes them as edgy and unjustifiably attacked). I think one mistake TV critics often make is assuming that audiences can only enjoy shows when they relate to the characters, or if they think the characters are cool or heroic or uncommonly real. I think it’s very possible for people to enjoy a TV show in totality without particularly liking the theme or any of the individual components. I would guess most of Entourage‘s biggest fans still make fun of it all the time. That’s part of liking it.


Yeah, and in that way it is exactly like Happy Days or Welcome Back Kotter or any more traditional sitcom. We like that we never see Horshack cry, just like we never rarely see Turtle cry, because it would be too weird for it to acknowledge that it kind of sucks to be Horshack or Turtle and have to follow around Vinnie Barbarino or Vince (is Vince the only name for an alpha male?). Any potential Turtles who show up in L.A. waiting for the free blowjobs and Audis to rain down on them end up just as disenchanted as the Carrie Sadshaws (TM Emily Gould) who move to New York assuming it’s brimming with available bachelors and glamorous party invites.

Don’t believe anything you see on TV? The sexism knock is the same one you could give Sex and the City, which is that it reduces the other gender to objects but then also allows some longer-term characters more depth and actual plotlines (just like Facebook/life!). The more we talk about Entourage the more fondly I find myself thinking about it. Television plays into loneliness by letting people feel like they are parasocially part of these fictional friend groups. They feel like they could belong. It is comfortingly predictable, and Ari is The Fonz.


Maybe, but maybe not. When I say people like TV shows that are “predictable and escapist,” I don’t think that’s necessarily a manifestation of weakness or loneliness. I think it has more to do with the unpredictable and inescapable nature of everyday existence. I think people are constantly trying to understand their own life and constantly trying to find meaning within that reality; this is an extremely difficult process, mostly because we’re all shackled by a fixed perspective. We can only experience life through our own eyes and our own memory. But TV is not like this. When we watch TV, we are watching (a depiction of) life from a detached, outside perspective, and we’re able to understand multiple experiences simultaneously: We can see Turtle’s life as Turtle sees it, but we can also see how people view Turtle and how accurate Turtle’s personal worldview is, and everything else that’s happening in Turtle’s world that Turtle is oblivious to. We are also watching something that was written with a definite beginning, an action-heavy middle, and a definite end (so a clear metaphorical meaning can always be deduced). It’s almost like watching escapist TV is a way to unconsciously simulate our own hopeless attempts at understanding ourselves, except with all the answers outlined at the back of the textbook. The static predictability of Entourage suggests that it’s somehow possible to understand actual life, and this feels good to people.

Also, that girl who plays Sloan has a nice neck.

Chuck Klosterman is the author of six books. His novel The Visible Man will be released in October.

Molly Lambert is a staff writer for Grantland.

Filed Under: Celebrities, Chuck Klosterman, Entourage, People, TV

Chuck Klosterman is a contributing editor at Grantland and the author of eight books. The latest is I Wear the Black Hat.

Archive @ CKlosterman