Nobody's Perfect: Entourage's 25 Biggest Fails

Entourage holds a special place in the hearts of many TV lovers. If not their hearts, at least a special place on the dorm room wall.

Just like college friendships and high school athletic ability, you might remember Entourage a little bit more fondly than you should. For teenagers everywhere, the show acted as a live-action Maxim magazine, delivering hot women, broad humor, and escapism in popcorn-light doses. Looking back at Entourage, you're left feeling that, while the characters didn't grow over almost a decade on the air, you certainly did.

How does the show look now? So few of the plot points are believable. So little is at stake for the characters. Like realizing that you weren't quite as cool as you remember yourself being in, say, 9th grade, revisiting Entourage is a sobering experience. The women still look pretty and Johnny Drama is still pretty funny, but that's about it. Cue up that Jane's Addiction theme song one more time because like it or not, Vince is doing the movie. Here are Entourage's 25 Biggest Fails.

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When: Seasons 7 and 8

From the end of his failed music endeavors in Season 3 through Season 6, Turtle's impulse to make something of himself lays dormant, thankfully. As the series came to a close, the writers must've decided that it's time to give Turtle some sort of meaning at the eleventh hour. The result: a string of dumb business ventures that either inexplicably succeed through the near-divine intervention of the likes of Mark Cuban or fail without any real repercussions.

You quickly miss the old pot smoking, devil-may-car douchebag Turtle, as the character is reduced to alternately looking very stupid in business meetings and pouting when things don't go his way as he fails to make something of himself again and again.

When: Season 7

Vince never has a noticeable drug problem until he hits his head. After a stunt gone awry, Vince cuts his hair, goes sky diving, takes up with a porn star (Sasha Grey), and develops a drug problem. You could spin the stunt as a metaphor for his rejection of those who have spent years controlling him, but Entourage isn't exactly a Douglas Sirk melodrama. If this was meant to be metaphor, rather than a fundamental misunderstanding of how addiction works, the show should have conditioned us by using metaphor at least once in the previous six seasons.

When: "Give a Little Bit" (Season 6, Episode 12)

Even fans who enjoy the relentless celebrity cameos have to admit that this episode is a bit much. Matt Damon, Bono, and LeBron James spend several scenes of the episode strong-arming Vince into making a hefty charitable donation. Every five minutes, one, two, or all three of them pop up to pressure Vince into cutting a check "for the kids." That's it. No tension. No backstory. Just a heavy dose of bad acting from all parties save Damon, and the inevitable capitulation of Vince. King James' performance makes you pine for the level of acting chops demonstrated by his forebears in Space Jam.

When: Seasons 1 and 2

If you're concerned about your characters coming off as tools when you first introduce them to us, we suggest you have them drive around in any other car besides a yellow Hummer H2. The yellow Hummer H2 is perhaps the douchiest car known to mankind. Watching backwards hat-wearing Turtle smoke up and feel entitled in that monstrosity made the show feel like a stealthy PSA in favor of environmental consciousness.

Unfortunately, it's far more likely that the Entourage team thought it was cool.

When: Season 2

You get the sense that studio notes were plentiful in Season 2. Right around the time they give Turtle a music producing career—don't worry we'll talk about it in a second—they introduce Vince's love affair with Mandy Moore.

Prior to this, Vince has been a relentless playboy, but we're supposed believe that beneath his Lothario exterior, Mandy has always had the key to his heart. Adrian Grenier and Mandy Moore aren't exactly Meryl Streep and Daniel Day-Lewis; they predictably have a hard time pulling off a destructive love affair. Though at first Mandy is ready to walk away from her man and Vince is prepared to sacrifice his career to make their relationship work, their fling is soon discarded, never to be mentioned again until the recapping and soul-searching of Season 8.

When: "Snow Job" (Season 4, Episode 10)

Vince and the gang are douchebags. All of them, even occasional moral compass E, think with their dicks more often than not, regardless of who they hurt in the process. Rather than force the guys to mature, the writers tend towards introducing male characters who are even bigger jerks. Pretty much every male character, from Billy Walsh (Rhys Coiro) to Scott Lavin (Scott Caan) seem introduced to make the main gang look good by comparison.

The most epic douche in the douche history of Entourage has to be Anna Faris's boyfriend Dave (A.J. Buckley), who refers to everyone as "dog" and demands E fetch him a soda while he hijacks his girl's photo shoot. Dave certainly succeeds in making E look good by comparison, just not at being a watchable character.

When: "Welcome to the Jungle" (Season 4, Episode 1)

Mocking the repetitive nature of Entourage has become something of a critical pastime. Vince is doing the movie. Vince can't do the movie. Vince and E have some tension. Ari has bigger fish to fry. Drama and Turtle fail to get laid. Everything works out in the end. The show's plotting is as dependable as a Chuck Lorre CBS multi-cam show.

And just when you think you're comfortable with the predictable turns, the beginning of the fouth season leaves you all messed up. The first episode is a half-documentary, half-narrative look at the making of Medellin, and it's about as sloppy as could be. The documentary portions simply repeat the narrative action we've just seen, and the mechanics of the documentary are quite strange: The crew interviews the star's agent and the producer, which isn't exactly customary for a behind-the-scenes piece. Just like the episode itself, the documentary doesn't know what story it's trying to tell, and ends up a tedious distraction. By the end of the episode, you're left wishing that we could get back to E talking to Ari on the phone and laying poolside dishing about his troubles with Sloan.

Yes, it is that bad.

When: Season 5

Even though the fifth season 5 starts to take some dark turns, the trend of celebrities bailing out the gang at the eleventh hour never goes away. Vince seems to be truly on the ropes at the end of Season 5. His career hits a serious skid after he's fired from Smoke Jumpers, his post-Medellin project. After a desperate gambit to land a role in Gus Van Sant's new film falls flat, things start to unravel.

Vince and E seem ready to confront their long-standing tension. Johnny Drama appears destined to finally leave acting behind. It looks like we might just see some true character evolution. Then, Marty Scorsese calls and offers Vince a role in his Great Gatsby adaptation. So much for lessons learned.

Next we see the gang, they'll be back in L.A. E will be Vince's manager again, and things will be as they've always been. Out of all of Entourage's numerous cop outs, from a story perspective, this one is the most disappointing.

When: Season 3

Here's another moment that could've fundamentally altered the show. How would the series have gone if Ari and Vince had parted ways? Ari takes Vince back with little resistance, but holds grudges against anyone else who wrongs him in the run of the show. What if Ari set out on a quest for Vince-vengeance after being canned? Who can say how that would've gone, but almost anything would've been better than Vince and Ari's easy reconciliation at the end of Season 3.

Vince gets a new agent, sleeps with her, there's a funny scene set outside of a synagogue, and then it's back to business as usual before season's end.

What did you expect? We all know that no woman can get in the way of an Entourage bromance, no matter how good the sex may be.

When: "No Cannes Do" (Season 4, Episode 11)

There have been no shortage of celebrity-guest-star-saves-the-day moments on Entourage, but this one is far dumber than the rest. Despite a code red at LAX, the gang manages to secure a ride on a private plane to Cannes (after a nice bit of racial profiling from Johnny Drama), but there's a problem. There are only five seats on the plane and there are six of them!

Vince, following standard Vince Operating Procedure, decides that if the whole gang can't go, none of them will go. How will they sell Medellin if Turtle's basketball jersey and Drama's bowling shirt aren't skulking in the background begging girls to doff their tops? As though he's sent by the Celebrity Travel Gods, Kanye West appears and offers to give the gang a ride to France—after all, it's on the way. Why does he do this? Like every other cool person in the entertainment business, Kanye knows the guys personally, of course.

Cue the obligatory close-ups of with hot stewardess asses, we're going to Cannes with Kanye, baby!

When: Between Season 1 and Season 2

"Not bad for some guys from Queens."

Throughout most of Entourage this is the battle cry that justifies the poor behavior of Vince and friends. Hey, they rose from poverty, so they're entitled to all the pussy and cars they can handle with no consequences or work. Even David Simon would have trouble selling that line if he were the showrunner and E, Turtle, and Drama hailed from The Wire's Baltimore. If you are going to pull the "started from the bottom" card, at least show us what you're talking about.

The gang leaves L.A. for New York at the end of the first season to film Queens Boulevard. They talk about staying with their families and returning to their old stomping grounds. If they had done this episode, rather than putting it off until the end of season five, we may have had more sympathy for the gang as they embarked on their three season-long party tour of Los Angeles.

When: "Malibooty" (Season 4, Episode 3)

Generally speaking, Drama and Turtle subplots involve the two of them failing to get laid. These arcs are often surprisingly funny. Their one-upsmanship of each other in "The Sundance Kids" (Season 2), resulting in a bunk-bed threesome, is one of the better Entourage moments.

However, these plots are far less palatable when the woman is the butt of the joke and not the bumbling duo. In "Malibooty," Colleen Camp plays an overweight woman who Turtle is asked to bed so that Drama can hook up with a legendary retired Hollywood groupie, Donna (Lisa Rinna). The humor, predictably, is derived from finding out which of the two of them is going to be forced into bed with a big woman. In this episode, we learn how cruel the show can be to women and just how unfunny Drama and Turtle plots are when the joke isn't on them.

When: Season 8

After years of get-rich-quick schemes, desperate attempts at getting laid, and driving people around, Turtle finally gets what he deserves: millions of dollars? Though E and Vince certainly get more than they've earned once all the chips fall, you can almost buy it because they've made some moves towards their goals, if in a circuitous route. At the end of the series, as always, Turtle is given undeserved gifts that prevent him from realizing what he is: a simple man clinging to a crowd of people who are smarter, better looking, and more motivated than he is.

They say you can't buy class, and if there is ever an Entourage spinoff following the backwards-hatted one into his life post-millions, we're sure that old saying would prove to be true yet again.

When: Season 1-7

Mrs. Ari, Mrs. Gold, Melissa, whatever you want to call her, she puts up with way too much of Ari's crap. Their relationship is by far the most fully fleshed out on the show, as most of the others are fleeting or involve non-characters like Sloan. Though we do appreciate that Mrs. Gold feels like a real person, we never quite buy her relationship with Ari because it lacks compromise.

For seven seasons, we watch Ari make promise after promise to his wife, only to break them after paying only the slightest of lip service. Yes, characters intimate that Mrs. Gold is a strong, smart woman not to be trifled with, but she folds faster than an origami expert when it comes to Ari.

She's continually either bought off by Ari's charms or by treating herself to shopping sprees to make herself feel better. When she does finally leave him (albeit briefly), we're left wondering what changed. Why did she put up with Ari for the better part of a decade (in addition to the years prior to the events of the show)? Even the easy explanation that she liked that cash doesn't work, as it is revealed that she came to the marriage with more money than Ari and that she stands to come away with a hefty settlement if they divorce.

We're finally asked to believe that she loves him—but that's the most tragic answer of all, as she's endured years of alternating verbal abuse and inattentiveness from a power agent, who either has no capacity for love or cannot express his feelings.

When: All Seasons

Shows set in the "real world" should beware of stunt casting. The result of the constant stream of guest stars on Entourage is that they have to tweak reality in strange ways at every turn.

Vince's A-list lover in the second season is Mandy Moore. In real life, Moore's career was never on the level of blockbuster superhero girlfriend, even right after A Walk to Remember (let alone after Chasing Liberty). Anna Faris's guest arc presents the same problem in the fourth season: She's treated like a far larger star than she really was.

Actors playing characters like Bob Odinkirk's financial guru in the eight season are often more recognizable than Hollywood players who play themselves; how many of us could identify Peter Berg and Mark Cuban on the street? Real-life directors and producers who can't act mingle with name actors playing fictional characters while little-known actors are obviously playing real-life figures who aren't available: the whole thing is a mess. Combine this with a Hollywood in which some real-life projects exist and others don't, and it's very difficult to keep everything straight.

When: Season 5

Entourage is the tale of two television shows. The first four seasons of the series play like a broad comedy. The action and the characters' pysches reset to one regularly. Emotional baggage and financial consequences aren't a part of the deal.

Though things continue to work out for the characters until they fly off into the sunset at the end of Season 8, our heroes undergo some serious alterations in Season 5. Vince is challenged by directors and producers. E's anger problem becomes more than a vehicle for humor. Drama's self-assured arrogance morphs into pathetic self-sabotage. We start to see the seeds of what will become Turtle's eleventh-hour self-awareness kick, as he slowly gains a tiny bit of perspective.

The problem is that the tone of the show from Season 5 on doesn't match what we've seen before. If you like the paper-thin plotting of previous seasons, the fifth year feels strangely dark. If you wanted a show with more stakes and a darker edge, then you turned it off around the second episode of the first season and watched The Shield.

One of the biggest knocks on the early seasons of the show is that there are no stakes, but feeble attempts to add bit to the show were no way to fix that problem.

When: "Amongst Friends" (Season 6, Episode 2)

Doug Ellin doesn't have the pop culture referencing sensibilities of, say, Kevin Smith, so it feels quite strange when Turtle spends the first few minutes of this episode quipping about Seth Rogen's ugliness. Rather than the usual "who got laid last night" banter that often begins a half-hour of Entourage, we're treated to Turtle musing about how he just can't believe Rogen with Katherine Heigl in Knocked Up.

At first blush, the bit is just a clumsily on-the-nose parallel to Turtle's situation, as he dates Jamie-Lynn Sigler at this point in the show. The truth is much worse. Apparently, Doug Ellin is a notorious grudge holder, and this was his way of getting back at Rogen for saying the show wasn't funny. Very mature.

When: All Seasons

Every show has to cater to its audience. Even the best HBO shows will find a way to include hookers or strippers somewhere in the plot. CBS ensures that all of their programming is terribly painful to watch and includes as much mugging as possible. Showtime shows are built around a damaged protagonist harboring a deep secret. The point is, executives understand brand. The brand of Entourage is straight teenage male fantasy, and any time fast cars, video games, and boobs can be incorporated in the show, they will be.

And oftentimes it brings episodes to a screeching halt. All right, it's someone's birthday, let's have a seven-minute scene involving the gang driving race cars around a track for no reason. Vince hasn't had a topless pool party for three episodes: let's get Central Casting on the horn. The problem with Entourage is never the pubescent dreamscape, it's stalling the plot to take viewers there.

When: "Good Morning, Saigon" (Season 2, Episode 12)

The first of several attempts to give Turtle some much needed character stakes arrives in Season 2 and is quickly abandoned. Despite demonstrating little interest in anything besides sneakers and weed, Turtle sets out to becoming a hip-hop manager in this episode.

For about a season, Turtle's arc involves working with emerging rapper, Saigon, his only client. As quickly as his short-lived career begins, Turtle is muscled out, and his career as a hip-hop manager is never mentioned again, besides a passing conversation with Saigon on the street and the aforementioned Kanye West guest appearance.

Maybe we're supposed to believe that the rap music used in incidental parts of the soundtrack is coming from Turtle's Hummer, because otherwise, this plot came came completely out of nowhere, and dissipated into the ether as quickly as it arrived.

When: All Seasons

Playing a bad actor is like playing drunk. The key to playing drunk is remembering that a drunk person wants the world to believe he's sober. When a bad actor is asked to play a bad actor, viewers must see a thespian who wants the world to believe he's better than he is.

Starting in Season 5, Vince's storyline becomes pretty interesting. He's forced to contend with the idea that he might be nothing more than a pretty boy. The problem is that Adrian Grenier is a real-life example of an actor whose eyes write checks his chops can't cash. Because the actor playing Vince is not particularly good, we have no concept of whether Vince is doing well in a role or not. As an audience, we are left in the dark, unable to side with any of the characters, as we've already suspended disbelieve to buy that Vince could become a star in the first place.

Entourage starring Ryan Gosling might have made an eight season re-watch seem far less of a chore.

When: All Seasons

At least Sorkin had walk and talks. For all the complaints and parodies that Sorkin's signature style has generated, at least the characters are in the same room with each other, acting in scenes. Many episodes of Entourage feel like this, almost entirely comprised of a series of phone calls. At some points, the show might be better enjoyed as a radio play. Just put some stills of sports cars and boobs on the screen, and the audio-only experience wouldn't be dissimilar to what we're already seeing.

When: All Seasons

With the exception of some last minute superficial soul searching as the series comes to a close, Turtle feels no shame for being a freeloader from beginning to end. He undertakes a few business ventures, but with the exception of his pursuit of the restaurant in Season 8, they feel like pathetic pastimes more than legitimate attempts at having his own life.

Viewers are supposed to find Turtle funny when he tells women that they aren't hot enough for him and lords access to Vince's house and drugs over model-actresses in vain hopes of fucking them. Sometimes he is funny, but mostly Turtle conjures pity in his best moments and repugnance during his worst.

Johnny Drama is consistently the most enjoyable character on the show, because beneath his arrogant exterior there's a certain self-awareness that touches us as deeply as a blow from Torvald's Viking Quest horn. Turtle, however, fails to move the audience. He's a clown with no self-awareness, which isn't very funny.

When: "The End" (Season 8, Episode 8)

Sentimental music and mood lighting can't make up for eight years of flimsy plot and non-existent character growth. Vince falls in love with a Brit. E gets Sloan back because she's pregnant. Drama gets to make his show despite another serious attempt at self-sabotage. Turtle is rich.

As the gang prepares to board yet another round of private jets, we're reminded once again that actions have no consequences in the world of Entourage. Even Ari, who's finally asked to choose between his career and his family, gets to have it both ways. It's no fun to watch characters get whatever they want, whenever they want it. The deep bonds between these characters, which the show so often retreated to as its moral center, was never truly tested, as the flow of women, cash, and career success never slowed for long, and times were never really hard.

The ending of Entourage feels like a going away party for a co-worker that worked next to you for ten years, but you never really knew. You spend the time before the cake-cutting grasping at straws, constructing meaning from something that, for all of its longevity, never meant all that much in the first place.

When: All Seasons

There are two types of women in the world of Entourage: castrating ball-busters like Dana Gordon (Constance Zimmer) and her boardroom colleagues, and trophy sluts for the gang to have their way with. The empty sexual encounters have nothing to do with the women. These characters are tossed to the crew as a carnal reward.

Vince books a movie: time for some sex. E finally leaves his lying girlfriend: He gets to bang a Perfect 10 model. Drama musters up some level of humility: time for a romp with a French babe.

Though David Duchovny's Hank Moody beds as many women as Vince on Californication, at least some of them demonstrate some semblance of character as Moody takes them from behind. Even if they're often naked, the women in Californication have needs and wants that sometimes conflict with Hank's amorous desires. The women of Entourage have about as much character and use as a new sports car or a renovated mansion: They are the spoils of a war too easily won.

When: All Seasons

There are enough examples of sexism and homophobia in Entourage to populate a list double this length, but if you're watching Entourage in the first place, you're likely willing to forgive the middle-school boys' locker room mentality on some level, so we'll be brief.

This series is a celebration of masculinity in its most shallow manifestations. Money and power buy sex. If you don't have these things, you are worthless. When women or gay men get power, they must act "straight" or their "weakness" will be mocked. Once they do conform to heteronormative power dynamics, the show labels them icy bitches and bitchy queens.

A show about bro-love will always relegate wives, mistresses, and gay colleagues to the sidelines, but Entourage often goes out of its way to remind non-alpha male WASPs where the show thinks they belong. All woman are models; all gay men are weak; all black men are rappers or athletes. If you don't conform to this world view, you'll be pilloried in Hollywood's town square, and you deserve it for disrupting the party.

Entourage is, at the end of the day, a fantasy. White heterosexual male fantasy.