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Coming of Age in Mississippi By Anne Moody
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Thank you! This book doesn't get a shred of the credit or press it deserves. It should be on every list right next to Black Boy as a chronicle of surviving Jim Crow. I happened upon it in a used bookstore a few months ago, and I just can't believe I hadn't heard of it before.
Another (short) book that is often overlooked is American Hunger, Richard Wright's sequel to Black Boy.
Mildred Taylor's books are also completely underrated. I read them in my early teens, but they aren't juvenile books in any sense except that the protagonist is young. In theme, language, history, etc., they're as sophisticated as anything else mentioned on the thread. Roll of Thunder, Hear My Cry is as good an education as you could get from any history book. Her book Song of the Trees, in contrast, really is for younger readers.