The Great Change: Turning Cathy into a Lawyer

An article in the NY Times entitled "His Hipness, John G. Roberts" led Ann Althouse to post with the subject line, "Some hipness and squareness about John Roberts."

That got me wondering about the origin of the pairing "hip" and "square," because you often run into people associating the two. And lots of time they do it in joking reference to the Huey Lewis and the News song, "Hip to be Square." But, I wondered on the HLN fan board, is that the etymological origin?

Apparently not, according to the drummer Bill Gibson. He thinks it comes from the beat generation and remembers his jazz buff dad using the pairing in the 50s. Which I guess helps explain why Huey used it as a lyric (his dad was a jazz drummer so he probably had heard the pairing too). But I'm still curious whether the song helped push (or give it a renewed push) it into common parlance. There's a lot of people who would know nothing of jazz or beat poetry who still use the pairing, so even if it technically had a different origin, for them it may have been the song that put it in their vocabulary.*

Any historical linguists who want to weigh in on this? I'm a bad measure of it because I first heard the song when I was 12, several years before I knew anything about jazz or beat poetry or was more widely familiar with common phraseology, and because as a fan in my mind I was always presuming the association, even if the people using the pair were not.

Incidentally, it's always been a sore point for the band that the song has been misunderstood. Most people take it to mean something along the lines that standing out uniquely is what's hip, but Huey was actually making the opposite observation. He's been quoted in interviews as saying that (in 1986 when the song was written) he was thinking about how people who had been such radical hippies in the 60s 20 years later had cleaned up so nice and become the conformist "squares" they used to rail about. The rest of the lyrics are consistent with this view. For instance:

I used to be a renegade, I used to fool around
But I couldn't take the punishment, and had to settle down
Now I'm playing it real straight, and yes I cut my hair
You might think I'm crazy, but I don't even care
Because I can tell what's going on
It's hip to be square

* Edit 7/10: To clarify, I don't mean that the words "hip" or "square" weren't in people's vocabulary. Or even, necessarily, that people didn't use them as antonym pairs. But it might be a generational thing, to some degree. People of my generation or younger do not typically run around using the word "square" to nearly the same degree as people used to, and the only reason they may be inclined to use it now is necessarily in oppositional reference to the utilization of "hip."

In fact, if true this may help explain why the song is so often misunderstood because to say "it's hip to be square" conjures up different ironic views for different people depending on how they define the word "square." For younger people it's the unique people who are squares, whereas it used to be the conventional people who were. For people like Huey the irony therefore is contextual, in that the popular, "hip" thing to do is be conventional. Whereas for others the irony is paradoxical, in that the popular, "hip" thing to do is be different. So maybe the etymological tracing of current "hip" and "square" pairing usage depends on which meaning of the word "square" the conflater tends to think of.