Hep, Hip and Cool
Back in the 30s and 40s the word was Hep and it later changed to Hip.
The definition of Hep and Hip is:
1. Keenly aware of or knowledgeable about the latest trends or developments.
2. Very fashionable or stylish.
Later Hip was presumptuously transformed and claimed by the generation that came after the Beatnicks and they called them selves Hippies. It seemed to make sense at the time, but in retrospect it is like naming your culture the Best-ies or the Supreme-ies. Or the Ourshitdontstink-ies. If you name a generation of which you are not a part, that's OK, but to name your own generation...it's just un-hep, un-hip and totally un-cool.
You don’t need to be hep or hip to be cool, though it is often implied There are cool people out there that show no signs of being hip or hep yet they are cool. Tesla was cool without being hep. Alan Greenspan was cool without being hep. Peter Sellers was cool without being in the least bit hep. Hip and Hep run away from Dennis Kicunich, yet he is so cool that it is nearly blinding.
Hep was a word of my parents generation. It’s a term I didn’t adopt into my lexicon until I started listening to Cab Calloway, but there was a time when in my twenties where I believed myself to be hip. No longer though. I know longer want that sort of responsibility. I don’t even want to be cool anymore. I am so secure in my apathy that cool no longer appeals to me in the least.