A decade ago, television's broiest show debuted, coinciding with the broiest years of many of our young lives, altering them, very slightly, forever. I first watched 'Trouge while living in freshman dorms, chasing Monarch Vodka with Rockstar Juiced (purple flavor) and marveling in the glory of a local P2P network which enabled me to download entire seasons of television in mere minutes. Subsequently, the homies and I waded through many a hungover morning binging on 22-minute episodes of Entourage, perhaps America's most prescient time capsule of mid-2000s extravagance.
Watching Entourage again as an "adult," it would be easy to be critical. The blatant sexism and celebration of excess make it an easy target, but it's more fun to look back at mid-2000s hilarity and to ponder if Mandy Moore was actually underrated. Entourage wasn't telling us anything we didn’t already know. Yeah, yeah, Hollywood is a vapid wasteland. But, shit, compared to the celebreality culture of 2014, 'Trouge seems almost, dare I say, quaint. It's just a show about a shitty actor making terrible career choices, while his friends siphon money and babes at every opportunity. Basically, it's how we imagine Shia LaBeouf's life is going these days.
At it's core, Entourage is a show about #thriving. The Four Pins official dictionary defines "thriving" as acting with the same reckless, fevered interest and indifference toward consequences as your 13-year-old self. Jumping a Razor scooter over two flaming skateboards? That's thriving. Stealing seven Coors Light from your dad and making out with babes on a trampoline? Thriving. Anything involving jet skis? Thriving. What's a better example of thriving in modern America than living off a talented friend whilst doing very little, if anything at all, yourself?
But how does one let the world know they're thriving, besides jet skis? Yeah, that's right, one's alphet. Thriving requires giving zero fucks and your attire must communicate that sentiment. The many fits of Entourage illustrate varying levels of thrive as each character ebbs and flows from peak to weak. And, yo, it's really been ten years since this shit first dropped, so you're finna see some of these hot early-mid-2000s trends on the runway or on some asshole influencer's Instagram in, like, six months anyway, so we might as well get a jump on that next wave of the nostalgia fashion money grab. Let's review.
Angelo Spagnolo is a writer living in Portland, Oregon. You can follow him on Twitter here.
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3. Vince1
Vince
'Trouge begins and ends with its protagonist, the flimsy, but charismatic Vincent Chase. We all have that friend who dresses terrible, but is so good looking he still pulls hella babes. It's frustrating as shit, man, I know. Is there any clearer illustration of this phenomenon than our bro Vince wearing a fucking full zip, ribbed sweater, while getting textual with your girl on that pre-Android device? Swagless and still smangin, an affront to nature.
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14. Debbie
Debi Mazar Appreciation
Debi Mazaar is criminally underrated and wildly unheralded as Shauna, Vince's no bullshit publicist. She goes obscenity for obscenity with Ari, flips shit to the whole crew, bosses around her hapless assistant Christie and sometimes comes with the space waitress cyber fashions and that's tight af. Plus, she reps Stephen Dorf and Gary Busey. Did you see Somewhere? It's actually pretty good, man.
15. Busey
Busey And The Great Lineage Of Washed-Up Celebrity Cameos
Usually, I'm not into the trotting out of Surreal Life cast members for cheap gags, but Entourage is unique in it's handling of the D-list. It works because Drama is somewhat in their league—a washed-up, aging actor who brings a sympathetic eye to the struggles of Pauly Shore, Gary Busey, Bob Saget and James Woods (who, like Mandy, kills it...as himself.)
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Kanye
The episode where Vince and co. catch a ride to Cannes with Kanye made me nostalgic for the days of Corny Kanye, when you could just throw on College Dropout and have a good time with your buds and not have to dissect Kanye's impact on the dominant cultural paradigms of our time. Miss that sweater vest (Pastelle?), 'Ye.
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Nicky Rubinstein
Entourage employs a lot of hyperactive Jews, but none more emphatic and erratic and, maybe, actually stylish than Nicky Rubenstein, financier of the eternally doomed Escobar biopic Medellin. Played brilliantly by veteran neurotic actor Adam Goldberg, Rubenstein can be seen here reenacting looking like me vacationing in Cape Cod, preparing to crush several lines from the bosoms of two hired babes.
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Turtle's "Bae Look"
That face you make when Bae says she can't hang tonight then 'grams drinks with "the girls," while you at home just smoking and playing Madden. SMFH.
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24. Saigon
Saigon
Speaking of Turtle's many missteps, his failed representation of IRL failed rapper Saigon was the beginning of his desire to forge his own career aka his eventual downfall. But dude still made $30k off not signing a rapper LMAO. Real talk, I'm the only dude in the world who stans for Saiginny, but that's because I read about him before he was ever on Entourage and because I'm one of the few who seem to remember when rap was about cool shit like crime and poverty. But fact remains, dude had a tape full of Just Blaze tracks and couldn't get any traction anywhere. V sad, overall.
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Billy Walsh In Mexico
Manic indie director Billy Walsh was always a favorite character of mine, given his penchant for strip clubs and general appreciation for #grimyliving. The Sundance wunderkind hits peak thrive while filming Medellin, and though the film eventually flops, I'd like to think Billy earned enough film nerd cred to land a deal modelling in the next Saint Laurent campaign.
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Drama On Five Towns
Drama finally getting a hit network TV show warms everyone's heart, but in the second season of the fictional NBC primetime vehicle, it looks like they hooked Drama up with the stylist responsible for bringing the L.L. Bean Signature aesthetic to an affordable pricepoint at your local JCPenney.
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The Fall Of Turtle
True 'Trouge scholars will notice this post stuck only to canon episodes, those from seasons 1-4. But just once we'll jump into the scary late-era seasons to witness what became of the once proud swaglord Turtle. Here he is in season 6 or 7 (it doesn’t matter which because neither are watchable), breaking the cardinal rule of #menswear: NEVER LET YOUR WOMAN DRESS YOU. The moment Turtle stopped wearing his fitteds, the show took a serious nosedive. Writers want you to believe static characters are boring—that characters must evolve. But Turtle's nonchalance was a pillar, steering the show back to its comedic roots if ever it veered. Like Turtle's continually failing business aspirations, Entourage should have stayed in its lane and focused on the silicon and silliness that made it great. R.I.P.
