I never got into the whole "hip" or "unhip" thing in the 60's. I either liked the music or I didn't. But then I've never been who anyone would mistake for a trend-follower much less a trend-setter.
In theory, there was mainstream, commercial music ( the Beach Boys ), and then there was "underground" rock (the Grateful Dead, say).
In practice, the underground bands wanted hits, and the mainstream acts wanted to be counter-culture
They should have covertly switched bands.