The 3 Worst Seasons Of Entourage

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The 3 Worst Seasons Of Entourage

When it comes to Entourage, most of us can spit out more lines than a bulimic does calories. It’s a show seemingly made for fraternity bonding during those drunken nights you wish didn’t end with a diploma, and it’s perfect… Nearly. Here is your guide to avoiding the wrong season “On Demand” next time you’re drunk waiting for a pizza or, better yet, a slam.

1. Season 7


The “Vince is on drugs” era gets off to an uninspiring start with Vinny’s unexplainable infatuation with Sasha Grey. Sure, I can see the value in a little #ButtStuff2k16 with the “anal queen,” but a supposed A-Lister begging for exclusivity (NF) with a semen demon known more for her cum eating than acting seems not only unrealistic, but fucking disgusting.

Vince squanders some opportunities, cuts his hair, and generally makes things difficult for Ari as he deals with his own marital woes. Turtle, in some sort of bizarre reverse affirmative action, scores a highly overrated, but still obscenely out of his league fully-shaved Latina (his first, in both respects. I’m sorry but is it still 1988? I know Turtle doesn’t pull like Vinny, but Jesus Christ), while Drama finds a way to best utilize his unique appearance: hide it as a voiceover.


Season 7 is a bigger series of disappointments than Steve Holt’s writing portfolio. Billy Walsh returns, but as a complete geed devoid of everything we loved about him — drugs, violence, and maniacal bouts of misogyny. Cum Dumpster nearly drowns Vince in her fluids, and nothing of consequence really happens aside from the dissolution of Ari’s marriage.

And, as a final public service announcement: the episodes with Dice bitching about his salary demands and insisting all of us understand he was sort of popular at some point when our parents were on this planet without us, are so intolerable I’d rather raw dog a knothole in a tree than watch again.


Vince getting cold cocked by Eminem’s security and Drama proclaiming “if it wasn’t for Jordan Farmar and that dude Kevin Love I would’ve killed somebody.” Season 7 cemented Drama’s status as that brother that LOVES to fight, but only before and after.


Like the last 3 years of Kobe Bryant’s career, Season 7 is just a series of embarrassing missteps and momentary nostalgia causing viewers to yearn for a much better time. The writing feels tired, the characters uninspired, and the storylines so convoluted and idiotic you’d think I wrote it.

If I have to choose just one, though, the 3-episode story arc of Sasha Grey attempting to convince Vince that her signing on for a 6-man gang bang was “empowering” and Vince offering her 7 figures not to do it, all while Ari erodes his personal life and football team.

Sasha proclaiming “I’m done” was a bigger relief than my last girlfriend’s miscarriage. Oh, and fuck Scott Lavin.

2. Season 8


Not coincidentally, the toilet paper to the explosive diarrhea that was Season 7 is a complete fucking mess. Doug Ellin attempts to resolve the “Vince on drugs” issue by castrating the former cocksman, leaving him in a proverbial rocking chair in a cardigan spewing fortune cookie cliché advice to his now oddly old buddies.

Turtle is rich as fuck for a nonsensical reason, “pulling an Entourage” when Vince conveniently admits he lied about selling stock in Avion Tequila (keep in mind the last two seasons were a giant product placement clusterfuck with a few moments of legitimate content sprinkled in) “because he just knew it would be huge.” I guess he got his MBA in rehab.

Speaking of Vince “just knowing” things, he realizes in about 7 minutes that the moderately attractive (and unbelievably cunty) reporter who refuses to fuck him for a couple episodes needs to become his wife in perhaps the most contrived and unbelievable moment of the series. Well, aside from Turtle continuing to pull.

Mrs. Ari dates, but supposedly doesn’t fuck, Bobby Flay (who surpasses Sasha Gray and the original Arnold the dog as worst actor in the history of Entourage) and Ari reignites those magic, rubberless nights of the early 90’s with Dana Gordon.

If E didn’t fuck Sloan’s mother (Step) while impregnating her, giving way to the most incredible Terrence outburst in series history, this season would be a strong competitor for the #1 spot.


Lazy, uninteresting, and surprisingly boring, Season 8 put a shit-covered ribbon on a show that deserved a crown. And no, the movie did not fix it. From uninteresting Vince and his desperation for the bitchiest woman in Britain to Scott Lavin become a recurring character, Season 8 went to shit faster than Johnny Manziel’s career.


Melinda Clark, aka Sloane’s stepmother aka possibly Emma Stone’s actual mother, gets E drunk and standard level E emotional, resulting in a sexual encounter with more instant regret than whoever the fuck banged Becky the Blimp.

As usual, Bob Saget is fucking amazing, but his 5 minutes of screen time are like the 40 years my ancestors spent wandering in the desert: not fucking worth it.

And, of course, Drama “swearing on his career” to a pregnant Sloane that E did not fuck her stepmother, and responding to Turtle’s concern for bad karma with “I had my balls crossed, bro.”


Turtle is an accidental millionaire, Vince gets married, and, worst of all, Bobby Flay tried to fuck Mrs. Ari in Ari’s home. That ginger genetic mistake deserved to run into Ray Rice in an elevator.

3. Season 5


If you can’t tell, I much prefer the “let’s get fucked up, buy shit, and fuck incredibly hot women” eras of Entourage to this emotional shit. If I wanted to be depressed as fuck I’d check my Bovada deposit history, not watch Entourage.

The season starts with Vince hiding out in Mexico, giving us perhaps the season’s greatest moment when an aspiring “actress” shows off a bootleg Jessica Alba level ass in her star-making performance anonymously riding Vince’s cock. Eric, as he is prone to do, puts his Sbarro degree to good use humiliating Vince with Carl Urtz, finally prompting his much-overdue firing.

In without a doubt the most “holy fuck, come on!” moment of the series not involving Turtle’s supposed lack of virginity, Vince secures the lead in a Scorsese adaptation of The Great Gatsby (so, was Leo busy?) while drinking himself to death in his mother’s Queens shanty. We waste 11 episodes finally seeing Vince’s downfall for it all to be completely erased in 30 seconds of idiocy.

Drama is a bit of a saving grace, though his relationship with French Jackie is more obnoxious than the wifed up brother until a disastrous break up prompts a Mickelson-at-Winged-Foot level meltdown.


Probably the only stretch of episodes that are legitimately boring. Vince’s “comeback” is mostly him bitching about how hard it is to sit around with your best friends banging chicks and accruing debt. Vince, it’s what us fraternity guys do every day and its fucking amazing, so stop.

The relief of Eric’s firing erodes into disappointment faster than a false negative pregnancy test, while Vince’s renewed Justine Chapin love wreaks of desperation like a half-chubbed closing time “talent sweep.”

Not a single episode from Season 5 is in my top 10 overall list, the only season without at least one representative.


The guys taking shrooms and bugging the fuck out in the desert is all too relatable. Shit gave me PTSD. Not that I’ve taken shrooms, or anything.


Realizing after episodes 1-5 that you have spent almost 2 full hours of your life you can never get back watching absolutely nothing happen. Close second: Dom comes back and proceeds to ruin another two episodes.

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