My definition of hip, musically speaking, is a bit backward — literally. I find it far cooler to have a knowledge and appreciation of music from before your time than the stuff being released tomorrow. Like my super cool niece, who is 12 years old but worships The Beatles. That’s hip.
I’ve always considered myself rather hip in that sense. In my teens (this was the late 80s), I bought and devoured every Bob Dylan album, then tackled the whole Beatles catalog. I was into Led Zeppelin and The Who and (especially) Pink Floyd. I had a passing knowledge of The Rolling Stones and The Beach Boys. I wasn’t Robert Christgau, but I was pretty hip.