The Ten Douchiest Moments in ‘Entourage’ History

Google “entourage douchebag” and a link from Warming Glow appears third on the search list. That is unacceptable: this should be the foremost website for pointing out the douchebaggery on TV’s douchiest show, “Entourage,” which premieres for its eighth and final season this Sunday on HBO.

With that in mind, and with the wonderful thought of the show finally being off the air after seven years and approximately five clever jokes, here are the 10 biggest douchebag moments from “Entourage.”

10. Mark Wahlberg’s Ego.

Unsurprisingly, “Entourage” is based on a douchey concept. According to executive producer Mark Wahlberg, “My assistant wanted to film my friends around me, because he just thought it was hilarious.” AREN’T MY FRIENDS AND I JUST THE LIVING END? I’ve always thought of “Entourage” as the most taunting show in TV history. Shallow Hollywood jagoffs can get all the free booze, drugs, and booty they want, simply because they’re either good looking or once starred in the 1988 remake of The Blob, while the rest of us Joe and Jill Student Loans have to pay for bad beer and even worse sex. “Entourage” shows us what we’re missing, and rubs our faces in their asses that have never felt the horrific touch of $.69 toilet paper. And Wahlberg’s quote does nothing to disprove this.

9. The Seth Rogen Controversy.

Why mess with Seth Rogen? He’s supposedly one of the nicest, most normal guys in Hollywood, and his TV show and movie track record is pretty damn flawless. Yet, in 2009, Turtle wondered how Rogen’s character bagged and bedded Katherine Heigl’s Alison in Knocked Up, a film that had come out two years earlier. And by the time the episode aired, it was well known that Rogen had dropped a ton of weight for his upcoming role in Funny People. If you want to make fun of someone for being fat, whatever—it’s an easy joke, but fair game. But at least do to it in a timely manner and to someone who’s actually deserving of chubby scorn. (Rogen’s response to the comments: “Yeah, those guys are assh*les…Luckily I never have and never plan on watching “Entourage.”) Also, fat people shouldn’t make fun of other fat people. So f**k you, Turtle.

[Editor’s note: “Entourage” creator Doug Ellin notably didn’t respond to Rogen calling him an assh*le — until there was a new season to promote. That’s when he undercut Rogen by saying that he had considered Rogen for the role of Turtle. And for what it’s worth, the original Knocked Up dig probably had something to do with Rogen talking candidly about HBO passing on a similar project of his before picking up “Entourage” — “You start to question your own sanity. Like, ‘Our HBO pilot isn’t funny, but Entourage is?’”]

8. LeBron James, Humble Hipster Philanthropist

Whiny bitch Vincent makes $20 million a year, but he has to be convinced by LeBron James — sporting a pair of fake hipster glasses that would make even Terry Richardson feel like an ass — to give more than $10,000 to a charity for children (LeBron is donating a million). This all occurs in front of Vincent’s private jet that he’s flying to Italy, and shortly after Bono briefly appeared in a webcam cameo. It’s like the writers want us to hate the show. Other notable douchetastic guest stars: Tom Brady, James Cameron, Paul Haggis, Brett Ratner, M. Night Shyamalan, Jay Leno, and Lenny Kravitz.

7. Vince Fires E.

Eric “E” Murphy, played by Kevin Connolly, who still can’t ride on four-fifths of the world’s roller coasters due to safety concerns, is the only decent human being on “Entourage.” He’s been Vince’s best friend since they were both kids, and later becomes his manager. When Vince’s career begins to sour, E convinces him to audition for Gus Van Sant’s new film, and when he doesn’t get the role, Vince blames his manager/childhood friend and fires E in the middle of a street. Later, Martin Scorsese, who must have thought he was agreeing to appear in a remake of Enter the Dragon but his eyebrow got in the way when signing the contract, calls Ari and tells him that he wants Vince for a role in his Great Gatsby movie—because of footage Van Sant showed him. From the audition that E got him. Because it’s a TV show, Vince and E make nice at the end of the season, but if I were E, I would have continued to manage Bow Wow and hang out with Seth Green, the only two celebrities shorter than he is.

6. Ari’s Casual (and Incorrect) Racism

On a show full of douchebags, Ari Gold might just be the douchiest of said bags. Case in point: his treatment of his poor assistant, Lloyd. Much of the show’s supposed humor can basically be boiled down to: ISN’T IT FUNNY THAT LLOYD’S GAY? AND ASIAN? HIS EYES ARE DIFFERENT THAN OURS, AND THAT’S AMUSING. IT’S HILARIOUS WHEN ARI CALLS LLOYD AN ASSHOLE BECAUSE THAT’S WHERE GAY PEOPLE HAVE SEX. HAHAHAHA*. The worst offense: after spotting a speck of dust in his office, because the cleaning staff is on strike, Ari scolds Lloyd and says, “You’re Asian, you’re supposed to be a neat freak!” Is that a thing? I know Asians are bad drivers, good at math, and they say “rong” instead of “long,” but has anyone actually ever said, “Look at that Asian; I bet his kitchen is spotless!”

*Note: actual writer’s note

5. This scene.

I take it back: there is a character worse than Ari and his name is Scott Lavin (played by Scott Caan, who’s now busy looking like a steroid addict on “Hawaii Five-0”). Like E, he’s a manager, and the two do not get along. It all begins with a fight over Bob Saget—and it’s not over who doesn’t want him—with the hate culminating in a tense table tennis scene involving women inexplicably dancing in their underwear, Vince having a threesome thanks to a game of Truth or Dare, Scott saying “mature” like the word rhymes with “manure,” a double dare involving arm wrestling, a punch-for-punch in the face offer, and the phrase “That’s not my hat, is it, bro?”

4. Shameless Car Porn.

It feels like half of “Entourage” is made up of the World’s Coolest Gang That You’ll Never Be a Part Of looking at, buying, or racing cars. There is, of course, the infamous 50 Cent scene where he’s listening to his own music, not to mention Ari’s asshole license plate (ARISFRRI). But my favorite moment of disguising your self-hatred by buying an expensive automobile is when Turtle, E, Drama, and Vince head to California Speedway to drive Ferraris around the track. Scored to a subpar Van Halen song, the whole thing smacks of effort, man. After the race, Drama says that he should buy a Ferrari, to which Turtle responds, “In this economy? People would think you’re a real douchebag.” Two seconds later, Turtle sees a $200,000 car and says, “Forget what people think. This thing is a beast.” To top it off, he’s wearing a polo shirt and a Yankees hat.

3. Selfishness Bordering on Anti-Semitism.

Thanks to a tip from his cousin Ronnie (of course he has a cousin Ronnie), Turtle is convinced that Sandy Koufax is going to pass away any day now and that he, along with Drama, should purchase a $64,000 game-worn Koufax jersey. The rumor turns out to be false, and Drama in particular is pissed that they spent so much money on a piece of clothing. Which is to say: the real reason he’s upset is because a good man, a man who was a Jewish hero and inspiration for young kinders everywhere in a pre-Adam Duritz world, isn’t dead. In other words: Drama and Turtle are both anti-Semites.

2. Emotions Are For Fags, Bro.

In the “Entourage” universe — or at least the minds of Drama, Turtle, and Vincent — being in a relationship is the worst thing that can happen to a man. To quote Drama, “it’s not natural for a male” to settle down with a female, and then he asks E whether he’s ever had unemotional sex. NO HOMO, BRO. Because, obviously, the worst thing about having sex is when you feel good. The guys on “Entourage” are just as bad the men who call sex “making love,” but in a more obnoxious, overt way: they flaunt their dicks all over California, and are shocked when every pretty lady they pass doesn’t want to rip off her clothes on the spot. (Also, if you notice in the clip above, nearly every person the guys pass on the street is a gorgeous, tall woman, and almost all of them stop and look around when they’re passed by Vince & Co.)

1. The Emotional Pitfalls of Dating Porn Stars.

To the four females who consistently read Warming Glow: I’m sorry for my gender. We’re awful, awful people and I don’t know how you deal with us on a daily basis. In the seventh season finale, Vince breaks up with his girlfriend, porn star Sasha Grey, because he doesn’t like her having sex with men on camera. You’d think Vince would have known what Grey’s profession is by the AVN Awards she keeps in her bathroom (including Best Three-Way Sex Scene and The Jenna Jameson Crossover Star of the Year)—and in fact, he does. But he’s also on coke, drinking Red Bull, and picking a fight with a male porn star also named Vince, so his reasoning defaults to “be a douchebag.” Sasha calls him out on his bullsh*t, saying that Vince has sex with random women all the time—at least she’s smart enough to get paid for it.

Ugh, I hate Vince. And “Entourage.”