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Is ‘Entourage’ a Philosophical Masterpiece?

Yes it's awful, but is it also an existential self help guide on par with 'The Alchemist'?

Image via Flickr user Ezra Wolfe

Entourage is horrible, but you already know that.

It's really not necessary to decode why Entourage is bad, that's pretty straightforward: it's offensive to women, men, homosexual people, heterosexual people, people in relationships, babies, and people with functioning brains.

Vince, E, Turtle, and Johnny Drama are the kind of rich people whose lack of self-awareness causes peasants to break into castles and cut off people's heads. Luckily they're in that gated community, though.


The movie wasn't any more offensive than the show, but it was less funny and less engaged with the mechanics of the oily, secretive, sleazy Hollywood system. But when it comes to the show, many people like Entourage but few will admit to it. I'm talking the kind of people who generally avoid nightmare garbage machines like Vince and his bro-culture friends in real life, but regard Entourage as a mindless, entertaining-behind-the-scenes mockumentary hosted by the Pussy Posse. So what is it about that show? Is it just that we like to frolic in the jizz-powered adventures of the idle rich and smugly laugh at these homies making homie-mistakes and woo-ing chicks with their classic homie-charm, while still remaining true to their homies? Is that wrong?

Maybe behind the tequila companies and the threesomes, Entourage follows a great literary tradition that actually has some philosophical weight.

Instead of evaluating why Entourage is shit, let's ask why it once worked. It can't just be Ari Gold's quips or Turtle's fledging rap producing career that have us hooked, the show is too repetitive for that. Maybe behind the tequila companies and the threesomes, Entourage follows a great literary tradition that actually has some philosophical weight. Vincent Chase parallels many spoiled protagonists in great American fiction, longing for a treasure that keeps slipping from his grasp: which in Entourage plays more like "Will Vince do the movie?" "Oh, he's looking like he won't do the movie!" "Oh cool, he's doing the movie!" Vincent Chase is Gatsby and international stardom is his Daisy Buchanan. Or is it his green light? Is E Daisy? Is Mandy Moore Daisy? Maybe we invest in Vincent Chase because he's doing what we want to do, executing one of the most pure existential journeys a person can undertake: he is following his personal legend.


In 1988, Brazilian author Paulo Coelho wrote The Alchemist, a self help book that was wrapped in an allegory about a shepherd called Santiago, a quest to find some treasure, and a whole lotta omens. It's one of the best selling books of all time and your year 10 literature teacher's favourite read. One of the reasons The Alchemist was so successful was that it introduced the concept of the personal legend. A desire that originates in the soul of the universe in which the planet conspires to help you achieve "what you have always wanted to accomplish".

Readers loved the concept of personal legends because it sounds like a sweet ass deal. So, the universe is actually conspiring to fulfil my dreams? It's a myth that I can't control my destiny? There is no such thing as coincidences, just signs and omens that my personal legend is almost achieved? Fuck, yeah! I am convinced that The Alchemist is in every Hollywood agent's waiting room, ready to inspire young actors and comfort them by purring, "keep going, the universe wants this". The Alchemist is about following your dreams against all odds, odds like money, women, and being attacked by desert warriors. If that doesn't sum up Entourage, I don't know what does.


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Even though Vincent Chase is a millionaire playboy riding the ups and downs of stardom and Santiago is ah, a shepherd, their personal legends take them on similar journeys. Also, there're only two female characters in The Alchemist: one is described as "very pretty" and the other one doesn't have a name. At their core, both Entourage and The Alchemist are about pursuing material riches, only to conclude that the greatest riches are the friendships they develop along the way—and also, material riches.

Vinnie's Personal Legend is artistic fulfilment as an actor and enough mainstream success to keep those Rolls Royce's rollin'. Vince is 100 percent convinced he alone can control his fate, which explains the number of times he casually fires Ari and E in the delusion he knows what's best for his career.

Santiago had dreams to keep him on track and Vince has his homies.

In The Alchemist we're told "moving when luck is on your side" is the way of the universe. The universe wants you to succeed, fool! Vince's bad (and arrogant) business decisions are all built on his belief that things will just work themselves out, ignoring the 20 or so people it takes to keep his career on track. He almost quits Aquaman, does quit the sequel to work on the train wreck Medellin, burns a whole studio who vowed to never work with him again, gets fired from the set of his comeback movie for fighting with the director, and decides to try his own stunts and almost kills himself. He continually pushes his luck and wants the best of the indie and blockbuster world because he knows that ultimately it will all work out. And it does! His track record for picking projects isn't fantastic but that doesn't seem to shake his resolve. Vince may shows signs of insecurity throughout Entourage's eight seasons but there's always someone to remind him he's the shit. Santiago had dreams to keep him on track and Vince has his homies.

At the end of The Alchemist—27-year-old spoiler alert—Santiago realises "life is generous to people who follow their personal legend". Entourage is all about the rewards that come from following one's destiny: the rewards generally being cars and porn stars. Vince makes ill-advised decisions because he knows that being a star is his true destiny. Maybe aside from the jokes about self absorbed actors and the Drama's elaborate breakfasts, people like to watch Entourage because it's nice to witness someone with so much faith in their personal legend. It's life affirming to see someone follow through with a sometimes ludicrous dream.

Maybe. But yo, the guest stars are pretty cool too.

Follow Sinead on Twitter: @SineadStubbins

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