I would have to say Patricia Barber and she's a Chicagoan too. Talk about Ethereal, especially live. Goosebump territory for sure! Holly Cole is great and I really dig Sarah McLachlin (I met her actually about 10 years ago when she was touring for her Solace album). I also like (in no particular order) Tori Amos, Shirley Manson of Garbage, Liz Phair, Kim Gordon of Sonic Youth, Chrissy Hynde of the Pretenders, Patti Smith, Aimee Mann (as a soloist), Lucinda Williams, Bjork, Fionna Apple, Polly Jean Harvey, Kim Deal of the Pixies and later the Breeders, Kate Pierson from the B-52's, Courtney Love, Debbie Harry, Leona Ness, Margo Timmins of the Cowboy Junkies, Johnette Napolitano of Concrete Blonde, Gwen Stefani of No Doubt, Enya, On the same vein as Enya, Loreena McKennitt, Sinead O'Connor (simply amazing live).
Geez.. I hope I'm not missing any. I love music, what can I say? 😉 Oh.. I like to watch Brittney Spears, only I like to hit the mute on the tv when I do. 😉
Sal