cata comments on Book Recommendations - Less Wrong
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I can't really recommend a book I've only just started, and Hard-Boiled Wonderland and the End of the World isn't about rationality, nor is it obviously in the majority's tastes here (surrealism, repressed sexuality, unicorns).
But Clippy might like it more than most fiction. Paperclips promise to play some pivotal role in the next phase of evolution or the end of the world.
That's the only book I can think of that has ever made me cry.