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.

Has Entourage run its course?

I was introduced to Entourage about three years ago by my then-Wizard colleague and now-Marvel colleague Ryan Penagos, who passed me the DVDs of the first two seasons. I had heard tons about the show, which had a lot of buzz, and flew through those early episodes pretty quickly in time to hop on season three live. It's never been my favorite show on TV, but Entourage is definitely different from just about everything else out there and something I consistently look forward to on Sunday nights.

But after the sixth season premiere last night, I'm wondering if after a solid run it isn't time for Vince and the boys to call it quits.

When it premiered back in 2004, Entourage was an interesting look inside the film industry and the culture of fame based roughly on the real life events of Mark Wahlberg and other members of the production and writing teams. It also was--and remains--very much a male adolescent power fantasy of sorts, as burgeoning movie star Vinnie Chase and his boys get to live it up with beautiful women, ridiculously lavish parties, giant-size mansions and all the cool toys they can get their hands on. However, despite all that, the show succeeded not just with guys, but with ladies as well (my fiancee is a fan, though her interest has waned of late), simply because it's a well-scripted, well-acted piece of television that celebrates and analyzes a world that most of us are fascinated by.

The first two and a half seasons followed Vince's rise from mid-level star to megastar following the success of a fictional Aquaman film, as well as his buddies and brother emerging to various degress in their own endeavors and his agent, Ari, taking increasingly aggressive risks that lead to him being booted from his agency, forced to start his own, and briefly fired by Vince. Romantic subplots are interspersed throughout, but the really intense stuff is the interpersonal relationships between the guys and the trials of business. Vince's own mismanagement of his career, E's success on his own, Ari starting from scratch and even Drama and Turtle branchin out on their own is where the true meat of the show comes from.

I'd say Entourage arguably peaked in the second half of season three and into season four, but also began to show the first signs of cracks in the facade. Vince gets a new female manager (played by the always awesome Carla Gugino) who he naturally falls for. Meanwhile, both E and Ari work to secure the film rights to Medellin, Vince's dream project. Ultimately, Ari is able to get the deal done and returns as Vince's agent, while E hires Billy Walsh, a brilliant but eccentric director he had clashed with in earlier episodes, to head up the project, which he and Vince will produce. This leads to season four, which centers around the production, editing and release of Medellin, during which E has major problems with Walsh and even Vince, leading to some of the most tense and raw episodes of the show.

But honestly, as good as season four was, the tipping point was when Vince parted with Amanda during season three and rehired Ari.

The split between Vince and Ari was a watershed moment on the show because it was the first real sign in nearly three seasons that things could go wrong in the storybook lives of this crew. Obviously they were going to reunite eventually, because Ari is a huge part of the show, but the speed and ease with which it happened reminded you that as much as Entourage seems like a "real" examination of Hollywood life and politics, it is very much a scripted half hour show that relies heavily on formula.

Season four ended on another positive note, not for the characters but for the audience, as Medellin bombed at Cannes and it seemed as if Vince and his career were fucked. Indeed, the fifth season opened with Vince on a beach somewhere ready to abandon working as an actor while E and Ari prepared to focus on their own enterprises. However, the show once again quickly circled back to the status quo as Vince is lured back to L.A. and his buddies drop everything to help him rebuild his career.

Every time the fifth season showed signs of moving in a different sort of direction with Vince facing actual adversity, rather than him having to claw his way back, stuff just fell into place for him, right up through the season finale where he is seemingly down and our back in Queens but E somehow moves heaven and earth to get him cast in a Martin Scorcese movie. I found it more frustrating that throughout the season both Ari and E had chances to really break out on their own, particularly when Ari is offered a job as a studio head, but Vince basically guilts them into not advancing their own careers because (on a metatextual level) that would offset the rhythm of the show's dynamic.

It was in season five that I realized I really didn't like Vince very much. Adrian Grenier is a skilled actor who plays the role of the entitled pretty boy to perfection, but the writers have really made the guy tough to relate to or have a kinship with. We hear constantly about how Vince came from nothing and earned his way to where he was, so that was kinda cool in the early season because you figured "maybe this could be me," but time and again he has slacked off, acted like a child and generally done nothing while E and Ari save his ass time and again and he rewards them by whining when they dare to attempt success outside his sphere of influence. Kevin Connolly, who plays E, is actually given top billing in the credits, I'm guessing in part because he is an infinitely more likable character, but as much as you want the show to be about his journey, it never really gets to be.

And that's really the problem with Entourage at this point: you know what you're going to get and it's nothing groundbreaking anymore. The status quo is never going to be upset to any great degree. Ari is never going to be anything more than an agent. E is never going to leave Vince. Fuck, Drama is never going to be that successful because it would ruin their material.

So the big tension points of the sixth season premiere were that E might get his own house and Ari's assistant, Lloyd, wants a promotion. Even though Lloyd was the B-plot by far, it's the more interesting one, because when all is said and done, E is not going to get his own place and will continue to live with Vince and Turtle until the show wraps.

So here's the question: should Entourage keep going? Because the thing is, even though it is very predictable, it's also reliably entertaining if not exactly the trendsetter it once was. The material is still funny and entertaining, the casting for supporting roles and guest stars alike is fantastic, and Jeremy Piven sure as hell isn't winning those Emmys on his personality and charm. Entourage could run several more seasons and continue to be moderately successful, but it's also going to stray further and further away from being the exciting, unpredictable show it once was.

Do you go out while you can still at least remember being on top or milk the run you've got for all it's worth even when you know your best years are behind you? Given the subject matter of Entourage, it's a pretty ironic question to ponder.