Art is what you make when you’re not feeling cool.  Not that feeling uncool is the basis for art, but that coolness – prevents the creation of real art. The reason is simple: You can’t be thinking about your image.  Doing so creates a distance – a duality if you will, between you and the deeper thing you’re trying to express. There can be no such boundary. This is why art is so rare. I’ve only felt it a couple of times and even then, I’m not so sure.

Here’s the best expression I ever heard of this truth. It’s from Cameron Crowe’s film Almost Famous, a story about the coming of age of a critic.

Lester Bangs: Aw, man. You made friends with them. See, friendship is the booze they feed you. They want you to get drunk on feeling like you belong.
William Miller: Well, it was fun.
Lester Bangs: They make you feel cool. And hey. I met you. You are not cool.
William Miller: I know. Even when I thought I was, I knew I wasn’t.
Lester Bangs: That’s because we’re uncool. And while women will always be a problem for us, most of the great art in the world is about that very same problem. Good-looking people don’t have any spine. Their art never lasts. They get the girls, but we’re smarter.
William Miller: I can really see that now.
Lester Bangs: Yeah, great art is about conflict and pain and guilt and longing and love disguised as sex, and sex disguised as love… and let’s face it, you got a big head start.
William Miller: I’m glad you were home.
Lester Bangs: I’m always home. I’m uncool.
William Miller: Me too!
Lester Bangs: The only true currency in this bankrupt world is what we share with someone else when we’re uncool.
William Miller: I feel better.
Lester Bangs: My advice to you. I know you think those guys are your friends. You wanna be a true friend to them? Be honest, and unmerciful.