I'd recommend
Round Midnight, a sin-to-be-missed film starring the legendary and incomparable Dexter Gordon as aging jazzman Dale Turner. It's set in a Paris club and full of grab-your-soul-and-pull-you-into-another-world jazz (actually created by the man onscreen, no less.)
What's swank about it? Not much. What's hip? Well, if Dex's melancholy tenor ain't hip, then hip is dead. I'd say that watching it won't
show you "hip," but it could help you get in touch with your own inner, truer hipness. To paint a masterpiece you need a whole pallet of colors, and to truly be hip a cat has to dig a whole range of hipness, and Dex explores it all.
Not that I'm biased or anything.
