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I want to start here... Most of these are of no particular order but when I was a kid my sister brought home an album and played it over and over and over. I think I still know all of the words to every song. So here I go...
This is Carole King. I think her album, Tapestry, was the first album that... in it's entirety... to be an anthem for an entire generation of women. For the life of me I can't think of an album you could point to and say, 'You know what,' that album spoke for an entire generation of men.
.

This is
Alanis Morrissette. About two decades after
Tapestry,
Alanis Morrissette debuted with
Jagged Little Pill, which accomplished what I believe had only been done only once before... She had an entire album that spoke for a generation.
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This is
Crissie Hynde of
The Pretenders. To me, she is the perfect representation of Rock and Roll... and the Last of the Independents.
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.
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This is
Bjork, and she is so unique I can't even put her in a
category. This is a
weird comparison but she's kinda like
Joe Cocker. You either 'get it,' or you don't. By 'get it' I mean they either resonate with you or they don't...
.
.
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Debbie Harry of
Blondie. I think she was a pioneer of sorts...
Blondie experimented with several styles of music and as the face of the band, she pulled it off.