I will second Liz Phair, saw her open for Smashing Pumpkins last week! She is STILL gorgeous. This might sound crazy to some, but at one point (a long time ago), Kim Deal was super hot, and add that whiny voice-wow!
The most sophisticated and impossible to repeat female vocal is Anita O'day. None I know of ever improvised quarter-tones as she did. Not only the voice important, but the ability to manipulate. She's a true champion.
A guilty pleasure of mine as well, tzh21y. Heck, I don't even mind her music, though I wish they hadn't marketed her as Country, thereby depriving real Country singers of some deserved exposure. A real one who also looks real good is Australian Kasey Chambers, a real babe.
I find Norah Jones, her sister Anoushka Shankar (Ravi's other daughter), Melody Gardot and Susan Tedeschi some of the most beautiful and talented women in the music industry.
I would agree with some of the other posters here that looks alone are irrelevant. I think Patricia Barber has an amazing voice but she is not as good looking as some, but I don’t care. On the other hand if you are looking for overall looks and voice then I have to go with Stevie Nicks. Those multi layered flowing gowns she wore and the sense that some had that she was some sort of witch (how inane) along with that powerful voice were captivating. I saw her live once and guys kept throwing stuffed animals onto the stage. At one point after finishing a song she commented "You would not believe how many animals live at my house"! Well I certainly would have loved to see her animal collection. She was a sweetheart beyond all others.
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