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A couple of really hip films that come to mind are:
Paris Blues - Paul Newman as a jazz musician in Paris
Dangerous Liaisons (1960) - Roger Vadim's version of the story set in 1960's Paris
To get another perspective of the happenings of "On the Road" from Neal Caassidy's POV, read "The First Third".
There's a lot of poetry and novellas out there. The BIG names are Alan Gisnberg, William S. Burroughs, Lawrence Ferlinghetti, Neal Cassidy and Gregory Coroso. THere's also a collection called The Beat Reader which is sometimes a good way t go as an introduction.
Music & Art: Thelonious Monk is so very Beat. So is Jackson Pollock, Hans Hoffman and Elaine DeKooning.
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