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Really great article, trying to find the words for elusive feelings...it's so hard to write about music. The musings on entropy remind me of Thomas Pynchon's famous story of the same name, written during the post-bop years. That story always reminds me of jazz (maybe it actually is about jazz! I don't have it with me at the moment....).
For really thoughtful rock music, with complex, subtle melodies and sculpted soundscapes, I am a huge fan of Bjork - she's right up there with Joni Mitchell, but while Mitchell's work is an amazing fusion of jazz and rock, I'd say Bjork is more a fusion of classical/avant-garde and rock. Which I realize is not the point of this article, but there's something about going for the boundaries that links all of this music for me, including Bitches Brew.
Anyway, thanks Mr. Kamiya for a thought-provoking essay - it feels like you really wrote from the heart.