Del Close and John Brent define hipster and cool in their spoken-word comedy album "How to Speak Hip" released by Mercury Records in 1959. 

The album presents itself as a didactic tool to be used by the listener to learn the secret language of the 'hipster'. As a parody of language-learning tools, the album presents a course in 'hip'. Basic concepts such as "cool" and "uncool" are taught, as well as vocabulary building.

Here is one of my favorite tracks; "cool" accompanied with Django Reinhardt's pleasant instrumental "Out of Nowhere". Enjoy!

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