The bizarre, unsatisfying finale of Entourage

Entourage concluded—at least as a television show—last weekend and unfortunately didn’t little to dispel for me my view of it as a franchise that peaked early and hung on too long, an opinion I get the sense even most folks who stuck with it the entire way seem to share. I don’t think the show ever completely lost its way in the sense that you could still count on at least a few chuckles an episode right through the end and most of the cast plus several supporting players remained strong in their work, but it also had a nasty tendency to shoot for the moon and then always let you down.

It probably shouldn’t be surprising that Entourage aired its best material early on, as the refrain in these past few seasons increasingly became that they were great at set up, not so hot at following through.

When Entourage kicked off in 2004, it was a story of Hollywood excess and escapism that entertained without making you think too much, yet approached it’s material from a fresh perspective: We’ve seen countless shows and films about the young actor working for that big break and getting it in the end, but here’s a story that starts out after those credits roll, where the kid has just made it and we get to tag along and watch him enjoy the spoils.

Those first two seasons and even the first part of three were really the golden age of Entourage. You’ve got a likable, quirky group of guys who you get to enjoy watching navigate the waters of business, friendship and the social scene in Hollywood. The conflicts and relationships are raw and you want to see what will happen with them, be it E’s contentious dynamics with Ari and later Billy or how Vince is able to work around a failed tryst with Mandy Moore while filming Aquaman (that was a fun sentence to write).

The problems came as the show swelled in proportion and the priority shifted to bigger guest stars, bigger houses, bigger parties etc.; the characters didn’t so much grow as they became too big to fail.

If you like your protagonists—and hopefully you at least have some level of affection for them—you’re not generally rooting against them, but for the purpose of good fiction, some level of tension and doubt is necessary. At some point Entourage turned a corner where not only was there never any danger of the characters failing to achieve their goals, there wasn’t even a question that the status quo would bounce back like a rubber band no matter what strain was put on it. You see it as early as season three when it only takes a few episodes for Vince to hire Ari back as his manager after a lengthy build to their “break-up” and it continued to permeate from there.

The breaking point for me was season five, where after Vince’s “dream movie” Medellin bombs, he gets fired from Smoke Jumpers, he alienates E and retreats back to Queen to fade away, and he gets a call from Martin Scorcese out of nowhere to play the lead in a Great Gatsby re-imagining. It doesn’t matter how compelling the first two acts of your story are or how much crap you put the hero through if his solutions come so simply in the end. There wasn’t even a cliffhanger to end that season, everything was just fine with everybody, and for no real reason other than that things always work out for them.

From there on out, it was just impossible for me to really get invested in Entourage storylines. I thought there was real potential in Vince’s self-destructive arc last season, but I never for a minute believed he’d actually be brought down for more than an episode (he wasn’t). I wanted to get invested in Ari’s divorce or E’s umpteenth split from Sloan, but I knew the relationships would be resolved, and worse, I knew they would be patched up with very little explanation.

Even Turtle and Drama, who started the series as the lovable lazy loser and over-the-hill B-star brother ended up as a mogul savant and comeback kid respectively. Ed Brubaker noted on Twitter that there’s no group of friends where every single person achieves the level of success the guys on Entourage did, and (now I’m more extrapolating) while the initial disparity helped make these dudes really feel like your buddies, their enormous shared fortune by the end really squashed that.

The finale was such a commentary on and microcosm of everything that went wrong with the series as it continued I’d be a little surprised if the creators weren’t playing it at least a bit tongue in cheek (they used that “everything always works out for us” sound bite from earlier in the season too often in recaps and promos for me to believe they weren’t at least somewhat self-aware and referential).

At the center of the episode was Vince’s surprise engagement to Sophia. The storyline between these two introduced only a few episodes back was one that in simpler times I would have been intrigued by, as the idea of a strong woman was not interested in Vince and who he had to actually work to impress was a departure and contrast from his usual role as the pursued and Alice Eve played the part well. The lengths which he had to go to in order to even secure dinner with her set up what could have been an interesting courtship, particularly given how leery she was of him at first. It would have been interesting to see what he would have to do to ultimately win her over and if he even could.

When the finale opened, Vince had already gotten her to fallen in love with him over the course of a magical date that took place in between episodes, so we have no idea how he pulled it off nor do we ever get an inkling. It went so well that they’re now engaged after knowing each other a few weeks, most of which was spent with her being cold to his affection.

I kept noticing the entire episode was Vince telling everybody about the impending marriage but Sophia never making an appearance, so I was holding out hope there would be an interesting last minute twist like she had actually said no and he was just trying to use this event to solve his friends’ problems somehow or was having a breakdown, but nope, in the final two minutes she shows up matter of fact and ready to go get hitched in Paris, her previous objections to this guy glossed over as if she was a Stepford Wife, her dramatic change in stance never explained.

And that pretty much gives you the problems with Entourage the later seasons in a nutshell: Some fairly bold problems set up, but then when it comes time to solve them, they might as well all be settled “between episodes,” given how flimsy the explanations always seemed to be.

The other big storylines of the season that hadn’t already been dealt with before the finale were wrapped with similarly insulting ease. Ari’s divorce, the seeds of which had really been laid the entire series, was swept under the rug as he made the same appeal he’s been making to his wife all season, but for whatever reason this time she zigged slightly instead of zagging, so he quits his job and gets his family back; I’m not against the end result—Ari’s a great character, I didn’t mind him ending up happy even if perhaps the alternative might have been more interesting dramatically—but the getting there seemed so arbitrary. Similarly, E burned Sloan once again, this time by knocking her up and then sleeping with her ex-step mom, but while none of his various appeals all season have done any good, one talk from Vince and she’s ready to give reconciliation a shot. These things don’t feel like they happen because the resolutions were earned, rather it feels like they’re resolved because the show is ending and the producers realized they only have so many minutes left to tape.

A lot of stuff was seemingly left open-ended for the movie that’s supposedly to come including most of what I covered above, but while I know I’ll go see that, I don’t have much faith it won’t be two more hours of the same circular progression to get back to the same happy ending point.

There were a lot of things to like about Entourage. Jeremy Piven owned that role as Ari Gold to the last second and made every time he was on screen magic no matter what state the rest of the show was in; Kevin Dillon as Johnny Drama wasn’t far behind in that department. On the whole, the celebrity cameos were a treat and never really ran out of steam. The dialogue always rolled, from the writers to the cast.

But at the same time, whether you’re talking about the show as a whole or just about every plotline past season two, the story of Entourage is having a great beginning, struggling with the middle, and being forced to end rather than finding their way there.