On the natural side, Blossom Dearie. If you don’t recognize the name, think Unpack Your Adjectives and Figure Eight from Schoolhouse Rock. She’s a serious singer of jazz standards and such, but still in that same girlish voice.
And in a similar vein, Yeardley Smith (who does the voice of Lisa Simpson) has a pretty good set of pipes.
For a processed voice, listen to Laurie Anderson in some of her songs, especially O, Superman. She combines her natural voice with the processors to great effect.
One of my first thoughts was David Sedaris’s piece on, as a kid, wanting to sing commercials in the style of Billie Holiday – you have to hear it to believe it.
Leonard Cohen was once described as “having a voice like a burlap bag”, which I find to be a perfect description. I have noticed that as he has aged he has felt the need to add breathy backup singers to many of his songs. Completely ruins it for me. He was one person who could convey great emotion with his voice, and it doesn’t need to be obscured by backup singers.
Roland Gift, lead singer of the 80s band Fine Young Cannibals. I always thought he sounded as if he was singing with his tongue glued to the back of his lower front teeth.
Leonard Cohen is probably my number one pick, followed closely by Tom Waits. I like Dwight Yoakam’s voice, but it’s strange because it’s traditional, which isn’t really popular in mainstream country music anymore.
As for the ladies, I guess Billie Holiday by default because I can’t really think of anyone else at the moment
I can’t beleive this thread reached page 2 without mentioning the two craziest voices of 80’s new wave - Talking Heads’ David Byrne and Devo’s Mark Mothersbaugh
Check out the Incredible String Band, jsgoddess. Robin Williamson has a truly strange and wonderful voice (and for some inexplicable reason, whenever I crank up the volume, I wind up getting the whole house to myself).