This is a place to consolidate book recommendations.
I'm reading The Logic of Failure and enjoying it quite a bit. I wasn't sure whether I'd heard of it here, and I found a post here called Great Books of Failure, an article which hadn't crossed my path before.
There's a recent thread about books for a gifted young teen and a slightly less recent discussion of books on cogsci thread which might or might not be found by someone looking for good books.
So, what books or lists of books do you recommend?
I go through Meditations on a regular basis. I have found it to be singularly uplifting. It has never "flattened" my emotional state at all, but I'm not surprised that flattening is an outcome for some readers.
It's possible that the translation you're using gives the text a morose tone. On the other hand, I've enjoyed both of the translations I've read (My current one is Maxwell Staniforth's and George Long's.)