On that note, Kate Bush.
Kate Bush is NEVER uncool. How much do I love torturing my 9th graders with the song "Wuthering Heights?" Almost as much as I enjoy making them read "Wuthering Heights," which is equally awesome for me and awful for them.
If you taught math, you could play her song "PI", in which she sings a whole bunch of the decimal places beyond 3.14 ...
But as a math teacher who has LOVED Kate Bush since around 1983, it pains me to report that about 80-100 digits in, she loses track. I assume it was part of an edit that didn't get fixed, and she said "Who would ever know?"
I could play this particular game endlessly, as anyone looking at my last.fm page could affirm, but how about (just scanning my music collection list) Ryan Adams, Adrian Belew, Kate Campbell, Bruce Cockburn, Al Dimeola, Dream Theater, Emerson Lake and Palmer, Genesis, John Hiatt, Jethro Tull, Jellyfish, King Crimson, King's X, John McLaughlin, Pat Metheny, Scott Miller, Randy Newman, Pink Floyd, Porcupine Tree, Prince, REM, Todd Rundgren, Paul Simon, Spock's Beard, Matthew Sweet, Weather Report, World Party, Yes, and even
Frank Zappa.
Nobody's going to be asking me to program a show anytime soon (although I think I could do a pretty good job, dammit.)