Matt
IKYN Guy Groupie
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The term "hipster" has no real definition and it seems the original poster put a bunch of films that are popular with cinephiles who may also be hipster (liking Dr. Strangelove or Clockwork Orange has nothing to do with being a hipster). Some are broadly popular indies, Juno and Little Miss Sunshine, and some are just entire resumes of certain directors (Wes Anderson appeals as much to middle aged film critics as hipsters, so I think that is unfair). And some are just blockbusters like Alice in Wonderland.
Here are a few movies that I know hipsters love and I think for the record are great too:
-Scott Pilgrim vs. the World
-Fight Club
-The Boondock Saints
-Léon
-Harold and Maude
-High Fidelity
-Shaun of the Dead
-Donnie Darko
-Pi
-Requiem for a Dream
-I Heart Huckabees
-Heathers
-Serenity
-Kiss Kiss, Bang Bang
-Thank You For Smoking
-Grizzly Man
-Election
And all of those are good movies. In fact I think they're just good movies that appeal to "hispters'" sensibilities. Still great.
I think what really defines a hipster is that they are trying so hard to not try to be cool. Therefore they usually flock to what may normally be seen as a cult movie (Dr. Strangelove) or an off-beat, niche film (Scott Pilgrim), regardless of whether or not they actually like it. They embrace it, simply to be different and show how little they care about what others think (when in reality they flaunt how much they love these movies simply to impress others with their lack of caring). Scott Pilgrim sold pretty fast on Amazon. I am willing to bet quite a few of the people who bought it, haven't watched it since. They bought it to show how cool they are and how little they care because they like a niche movie that bombed. And that is what defines a hipster. So when you think about it, really any movie can be a hipster movie.