Time to take a smart chick:
Lisa Loeb
I considered literally dozens of ladies and lady groups for this spot before settling on the girl in the glasses. I think I perhaps have more 2 or 3 song female artists than any other group of artists for me, and a big thing here given the island premise is that not ony does Ms. Loeb have 4 or 5 top songs that are regulars for me, but I can listen deep into her catalog before hitting the first song that makes me want to hit the skip button. I also felt like my list has long been unbalanced toward the louder more uptempo stuff. That is where my tastes are centered -- I think perhaps as a level/analytical person I like music to get me up while excitable people sometimes like music to "chill" to, whatever that may mean. But still, the balance on my list doesn't reflect the balance on my ipod so I wanted to try to correct that somewhat.
P.S. Somewhat bizarrely Lisa has spent a nice chunk of the 00s putting out children's albums. I won't be taking those along. So I hereby delegate Lisa's version of Twinkle Twinkle Little Star to pdx.