The finale of Entourage was very heavy on romantic relationships. It sometimes seems like shows become romantic soap operas inevitably, inexorably. There was a lot of embarrassing material (“If he slept with [another woman], he did it over you”) and embarrassing jokes, but you probably knew that, because Entourage has not exactly been at its creative peak in a long time. As with any show that starts out strongly and suffers a decline, it’s almost hard to remember that it once seemed fresh and interesting. (Possibly it was more interesting because Larry Charles was one of the writer-producers for the first two seasons, but I have to admit that I don’t have strong enough feelings about exactly when the jump-the-shark moment was. It just seemed to be enjoyable, and then it wasn’t so enjoyable.)
Entourage always had its weaknesses and a certain air of smugness; the flaws that did it in are not new flaws. But I think it’s worth remembering what made it interesting at the time. There have been many insider shows about Hollywood, and they almost all bomb – think Bracken’s World, think The Famous Teddy Z, think Action. One problem so many of these insider stories have is that they tend to portray Hollywood as a ridiculously unpleasant world, even though we can see for ourselves that it isn’t. Action is Hollywood the way many people, particularly writers, like to see it: full of Philistine producers, backstabbers, nymphos and nastiness. The problem is that this mostly seems terrible to people who live in Hollywood, and therefore have higher expectations. To people who dream of living in Hollywood or getting anywhere near show business, it comes off as whiny.
So Entourage managed to make the Hollywood-insider concept a success by, in a way, portraying the happy side of Hollywood. It’s fun to be a movie star. It’s also fun to hang out with a movie star even if you yourself are just a hanger-on. Powerful agencies are more glamorous than they seemed to be on The Famous Teddy Z, where the lead character worked for a major agency that was rather drab and behind the times. And even failures in Hollywood seem kind of fun by comparison with failures anywhere else – when a Hollywood star’s career goes down the tubes, he does it with more money and more entertaining debauchery than most of us can aspire to, and being a down-and-out movie star means doing jobs that would seem like huge success to most of us (including most aspiring actors). It’s just not possible to convince us that these people’s lives aren’t fun. Entourage just ran with that, being openly and brazenly escapist. This, ironically, made it probably more realistic than the usual à clef Hollywood story.
The finale was a silly episode and the tag scene was silliest of all. Yet that scene seemed to sum up the show: Ari Gold is torn between one lifestyle that seems like an escapist dream to 99.99999% of the population, and another escapist-dream lifestyle. Which dream will he pick? Will we find out in the Entourage movie they keep talking about (which is more likely to get made than the Arrested Development movie, but that’s about all I can say for it)? The dilemma seems like a bigger budget version of something Michael Scott might have dreamed up in his “Threat Level Midnight” movie. And that’s kind of the point. Entourage probably wouldn’t work on a broadcast network, because while broadcast networks deal in escapism, their kind of escapism is about giving us the feeling that we can identify with these people – that they’re average Joes in some way, even if they have more money than us and live in bigger apartments. HBO came up with the perfect alternative for a smaller, paying audience: shows that give us a feeling of vicariously living other people’s incredibe lives. (Their most popular shows, from The Sopranos to Sex and the City to Boardwalk Empire to Curb Your Enthusiasm, tend to centre on ostentatiously wealthy or high-living people.) It got out of hand with Entourage.