Silicon Valley Is the Anti-Entourage

Photo: Kelly Chiello and Photos by HBO and Warner Brothers

On October 28, 2013, Entourage creator Doug Ellin announced that his hit TV show would soon return as a movie. Given the reaction, you would think scientists had announced they were bringing back smallpox. The website Bustle welcomed the news with the headline “The Film We Never Wanted Is Happening”; recently, comedy writer Wendy Molyneux was able to raise tens of thousands of dollars for charity by promising to sit through the Entourage film in return for donations. A series of brutal, hilarious reviews for the movie, in theaters today, has confirmed Entourage’s status as the Guy’s American Kitchen of film.

As antipathy toward the cinematic version of an old HBO comedy grew, a new HBO comedy was establishing its critical darlinghood status. Silicon Valley is enjoying the kind of buzz that once propelled Entourage. Reviews for the show are solid, it’s fresh off a Critics Choice Award win for best comedy, and in the disruptionary parlance of Silicon Valley, Silicon Valley is starting to look like a television unicorn.

There is reason to compare the two shows, and not just because Silicon Valley is hitting its stride while Entourage stumbles, friggin’ wasted off Jägermeister shots, toward its opening weekend. As Eric Thurm observed in Slate, Silicon Valley serves as a useful counterpoint to Entourage. Both series follow five men in California trying to succeed in their city’s dominant and defining industry, and yet the two shows could not play more differently. Silicon Valley is, in many ways, the anti-Entourage. Its characters, its plotlines, its cameo roles, its attitude, its overriding mood: Mike Judge’s San Francisco is like a Bizarro Doug Ellin Hollywood.

Why the 180-degree turn? Why does Silicon Valley please where Entourage grates? Perhaps this is a function of time, or our shifting comedic tastes, or our evolving attitudes toward wealth following the financial crisis, which occurred smack-dab in the middle of Entourage’s run. Perhaps we are all just getting meaner, and enjoy entertainment that is mean to its subjects.

Whatever the case, HBO’s Los Angeles show and its San Francisco show are about as different as — well, as L.A. and San Francisco. Here’s how Silicon Valley took the Entourage model and radically disrupted it:

1. Silicon Valley is actually critical of Silicon Valley.
Whereas Entourage generally glamorized and celebrated Hollywood, Silicon Valley often feels like a full-throated condemnation of it. It stomps on all that is frivolous, inessential, and overvalued in tech. The difference is not that Hollywood is free of frivolous, inessential, and overvalued Companies, People, and Products, but rather that Entourage doesn’t care to address them.

Part of that is because of the kinds of shows they are: Silicon Valley is a satire with occasional sincere moments, whereas Entourage is an irony-free zone, loath to poke at its subjects. Silicon Valley has landed some gnarly face-punches against many of its most high-profile residents this season: Targets include Apple Maps, Prius drivers, and Digg founder Kevin Rose, who was the butt of a wicked and harsh punch line during a Hooli board meeting.

Not so of Entourage, which could have been underwritten by the Hollywood Tourism Board. If Entourage is, as Chuck Klosterman once argued, an “idealised representation of being a happy person in Los Angeles …” then …

2. Silicon Valley is a takedown of the idea of happiness in San Francisco.
Entourage is peopled by grinning morons and inebriated Ed Hardy–wearing optimists; no character on Silicon Valley really ever seems happy for more than a fleeting moment. The show’s main set, Erlich’s house, is cramped, messy, and unglamorous, while the perks-fueled tech campuses are made to seem cheesy and oppressive rather than luxurious. Is it fun to live in Silicon Valley’s Silicon Valley? It doesn’t look fun. Is it fun to live in Entourage’s Hollywood? At the end of the show, with a vodka–Red Bull in hand, of course! Speaking of which …

3. Silicon Valley doesn’t always, or ever, end happy.
No one Gets the Girl, no one Lands the Part, no one Closes the Deal; there are characters from Gogol with cheerier outlooks and character arcs than Pied Piper CEO Richard Hendricks. Pied Piper’s peak moment of success — its victory at TechCrunch Disrupt, at the end of season one — was immediately followed by the CEO vomiting into a Dumpster. If the bros of Entourage had won TechCrunch Disrupt, the episode would have closed out in the VIP lounge of the Lure nightclub, supermodels hanging on everyone’s side. There’s an old parody video — starring, of all people, Thomas Middleditch of Silicon Valley — that traces out the stereotypical Entourage episode: Vince gets booked to do a movie. Something prevents Vince from doing the movie. At the last possible moment, something improbable allows Vince to do the movie after all. The crew celebrates and has much sex.

Not so in the world of Silicon Valley, which tends to end on the edge of a cliff. Silicon Valley is scripted such that it might be canceled mid-season, and it would take less than 30 minutes for Pied Piper to fold and for everyone to get back to their day jobs. The show tortures its characters where Entourage coddles and reifies them. And it’s not just the protagonists, either …

4. Silicon Valley mocks its cameo actors, too.
The defining cameo in Entourage is probably James Cameron, who appeared at the end of an episode, flying a helicopter for some reason, to offer Vince a leading role in a big-budget superhero thriller. Cameron was presented as a larger-than-life superhero himself, and with few exceptions, celebrities who graced Entourage may as well have been surrounded by halos of light. “Behold, ye unwashed masses, the great men of our time!” Entourage says to its viewers. “Bask in the munificent glow of Brian Grazer and Frank Darabont!”

So far, at least, tech celebrities on Silicon Valley have arrived to be mocked. The Winkelvoss twins made a brief cameo, only to be treated as uni-brained monsters by Erlich; Snapchat CEO Evan Spiegel poked fun at his company’s supposed overvaluation. Recurring characters based on the real-life personae of Mark Cuban and investor Peter Thiel have been brutal.

And yet despite — or perhaps because of — the mockery of the guest stars, the maltreatment of the protagonists, the constant existential blows against Pied Piper, there remains one key, elemental difference between the two shows …

5. The characters of Silicon Valley are worthy of their success.
Vincent Chase is a laughably bad actor. Two of his best friends are lazy, talentless hangers-on. And yet we are expected to cheer for Vincent to make millions of dollars for doing about 20 minutes of work every day, in part to support a bunch of freeloaders who somehow do even less work than he does. This has become an increasingly difficult sales proposition.

The Pied Piper team, meanwhile, are workaholics who know their stuff: They are constantly pulling all-nighters and reciting convincing-sounding code and technical know-how, and yet the show’s writers have been merciless with them. Any success Pied Piper wins (and it has won distressingly little, when you think about it, given that the show has been going on for over a dozen episodes) feels earned.

This might explain the lack of excitement for the return of Entourage: Shouldn’t these guys have moved back to Queens already? How is Vincent Chase still famous, 11 years out, despite no apparent aptitude for acting? Is there an Uber for Hollywood meritocracy?

Maybe that’s the pivot: In Silicon Valley season three, Pied Piper can middle-out compress the Entourage boys back into retirement — or at least write an algorithm that can teach them some humility.

Silicon Valley Is the Anti-Entourage