bleg: music to teach with

It's kind of early to bleg, but this week, I realized that I really want to use music more as a teaching tool. Two big issues that came to my attention this week:
First, my really wonderful 7th graders were studying Australopithecus Afarensis but didn't know "Lucy in the Sky with Diamonds" (which is fine because it's somewhat obscure), but they were woefully unfamiliar with The Beatles -- the answer I got was "hippies!" and we all know there's so much more to them than that. Secondly, my wonderful 9th graders are so punk that they think they don't like hip hop. If Talib Kweli was somewhat more accessible, I'd be playing his sophistication for them until they swore they absolutely adored it. But they also are really into punk in a cool way, and I'd like to introduce them to some Velvet Underground/Lou Reed as a way of introducing their proto-punkness in a highly educational, useful-for-teaching-English sort of way.

Of course, any suggestions need not be limited to the Beatles, Talib Kweli, and assorted Lou Reed projects. This article was somewhat helpful to me, but of course I won't limit myself to British music. My main criteria are that the lyrics are more or less clearly understandable, mostly uncomplicated without complex allusions, and that it's uhm, Catholic School appropriate -- otherwise, I'd be doing Cocaine Blues right away! ;)

So please, leave a comment with any suggestions and have an opportunity to corrupt the minds of youth. I have some ideas, but I'm curious about what you think and would suggest.