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Derived in the late thirties; early forties. Serious jazz lovers. The times to define the difference between the cool and the uncool. When snapping fingers took the place of applause. Unhip gave a flavor like the term "little grass hopper"; a student.
When someone tries to compare Miles Davis and Louis Armstrong as the same horn ...
Not only will a serious lesson follow but towards the end, an underscathing tone of "unhip one".