Clearly, there is nothing “hip” about Will Hunting. He works odd jobs and has no concern with his appearance or what’s “cool,” but his values overlay perfectly with the hipster ethos so much that I’m making Will Hunting and honorary hipster.
His lack of motivation and fear of failure has caused him to reject both ambition and human connections outside of his childhood friends, who may actually go down as the best group of friends in the history of cinema. Granted, Will’s alienation comes from being beaten by foster parents more than it does a general lackadaisical shittiness that oozes from most hipsters, but the effect is the same. His arm’s length superiority ultimately proves to be the prime cause of his failures as a person and a boyfriend.
But beyond all that philosophical shit is that line when he meets Skyler about going to eat a bunch of caramels because it’s as arbitrary as meeting for a cup of coffee. That’s so something a douchebag hipster would say.
No surprise here. The thirty-something Chicago record store owner is a hipster. While he doesn’t affect the hilarious condescension for popular taste like his employees do (Jack Black’s Yanni shirt), he is stuck in an adolescent whirlpool where he keeps making the same stupid mistakes with women, but being too much of a pussy to make any changes.
Sure, Tim Robbins’ Ian “Ray” Raymond is the more obvious answer here with the ponytail and the tinted glasses and “patchouli stink,” but we never get to know Ray. We get to know Rob pretty well, by the end, and I can’t say that I feel his whiney ass deserves her. I think he should live in a duplex with his two employees for the rest of his existence.
I hate Napoleon Dynamite. Napoleon is a hipster who simply lacks the quality of being self aware. He dresses like an asshole, has quirks left and right in the form of tater tots and liger drawings, and he’s certainly got that undeserved air of superiority in spades. Further, he is absolutely intolerable, even in small doses, and the very site of him makes you want to bite his eye socket like a rabid chimp.
That might not be a sentiment unique to hipsters, but it’s certainly how I feel about most of them.
The poor girl is only 15-years old, so she can’t be a proto-hipster. Perhaps she’s a meta-hispter in the making, as the hipster movement was in full-swing by the time this moppet popped up. Either way, at such a young age, she’s already talking about Mott the Hopple and Dario Argento films, so I had to put her on this list, even if she doesn’t quite fit. I feel horrible saying this, but the world would be best served if they had euthanized both Juno and her unborn child. Frances Bean Cobain has a better chance at normalcy than Juno Jr. did with Juno and Paulie as parents. That poor bastard will have Frightened Rabbit played as lullabies while being taught ironic barbecues are a normal part of one’s upbringing.