Cool only exists in the context of a subculture. Surfing may have been cool in the 80's in your cultural experience, but certainly not in everyone elses. (I would have pegged it in the 60's myself when all the Beach Blanket Bingo movies were made)

I think we need a name for the philosophy of cool - Morality gets ethics, Beauty, Aesthetics - Coolics? There's got to be a better term.

Surfing, Beach Boys, 60's, absolutely.

But what would all the surfers I drive by every morning on my way to work think?

From the examples above - that 20 years from now their culture will consider them cool ;)