I agree with Idril - A Heartbreaking Work is wonderful. Really depressing, but funny at the same time. So you feel terrible for laughing. It kind of confuses your reactions...
I'd also suggest Dreams of My Father and The Audacity of Hope by Barack Obama - though some may argue that you'd have to support him to appreciate what he has to say. I don't necessarily believe that.
And I know it's old-school, but the Autobiography of Benjamin Franklin is a good read. I read it a few months ago and I was struck by how we're told in elementary school that he's a hero, but then we read his autobiography in college and we begin to think he was a bad person. I reread it again in grad school a few years later and came away with the impression that he was just a normal man with a very sophisticated idea of public identity. Maybe it's just me, but I think he had a few things figured out.


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