18 Years Ago Today, ‘Entourage’ Premiered On HBO — Here’s Why We Still Love It
— Updated on 14 March 2023

18 Years Ago Today, ‘Entourage’ Premiered On HBO — Here’s Why We Still Love It

— Updated on 14 March 2023
Garry Lu
Garry Lu

On this day in 2004, HBO’s Entourage hit the airways, inspiring an entire generation to dream about the 21st-century Hollywood lifestyle. And while neither the fashion nor social politics featured within Doug Ellin’s classic dramedy have aged particularly well, it’ll forever hold a special place in our hearts.

Granted, Entourage is loosely based on the antics of Mark Wahlberg and his own hometown crew, and yes, it depicts a version of life the vast majority of us will never experience. Despite this, there’s an undeniable element of relatability that threads all eight seasons together. One that perfectly distils the broad strokes of male comradery, of enduring friendships – and in the case of foul-mouthed power agent Ari Gold (portrayed by Jeremy Piven) – the broad strokes of ambition.

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You needn’t look further than the gang itself. We might not personally know an overnight success story or a pizza restaurant schmo turned bona fide manager to the A-listers, but we certainly recognise the key archetypes:

Vincent Chase (Adrian Grenier)

The pretty boy who’s been kissed on the tip his entire life and coasts from day to day on Easy Mode. His redeeming quality? He never forgets where he’s from and always makes sure his boys are along for the ride with him a la George Clooney.

Eric “E” Murphy (Kevin Connolly)

The level-headed bloke who stands a little too close to ever see the bigger picture, often to the detriment of himself, always to the detriment of his romantic pursuits. He’ll never be another yes man, which you should be grateful for.

Johnny Drama (Kevin Dillon)

The operator with ambitions that exceed his intellect, ability, talent, and looks. That being said, there’s not an uncaring or insincere bone in his body. He wears his heart on his sleeve and constantly has your back.

Salvatore “Turtle” Assante (Jerry Ferrara)

The fella you always little-brothered and were content with keeping around as nothing more than a reminder of the good old days. Eventually, he came into his own, and you’re rooting for him to improve his station in life however he sees fit.

Ari Gold (Jeremy Piven)

Just a straight-up gangster. There’s not much else to it. We all wish we could get away with being that hilarious, ruthless, and capable at the same time.

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In an era defined by uncertainty and the ever-bleak prospect of tomorrow, HBO’s Entourage represents the escapism we all crave; the simplicity and promise of opportunity seldom afforded to us in real life.

When you really boil the series down to its core essence, take away all the plotlines about starring in James Cameron’s Aquaman and dating Sasha Grey, it’s about a bunch of mates who’ve achieved status, wealth, and fame beyond their wildest imagination — who remain virtually unchanged as friends in the face of said status, wealth, and fame.

Occasionally, they grapple with a setback, lose a job here and there, maybe even check into rehab to kick a cocaine addiction (who amongst us hasn’t?). But unlike reality, it’s nothing that can’t be solved over the course of an episode, sometimes several.

There’s always a bigger paycheque around the corner, a shinier car waiting at the next dealership, and in one particular case, Martin Scorsese on the other end of the phone. That’s why we love Entourage.

Now… relive Ari Gold’s finest moments below.

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Garry Lu
After stretching his legs with companies such as The Motley Fool and the odd marketing agency, Garry joined Boss Hunting in 2019 as a fully-fledged Content Specialist. In 2021, he was promoted to News Editor. Garry proudly retains a blue belt in Brazilian Jiu-Jitsu, black bruises from Muay Thai, as well as a black belt in all things pop culture. Drop him a line at [email protected]


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