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Currently reading Fooled by Randomness, almost 20 years after it was published. By now I have read about a third of it. Up to now, it seems neither very insightful nor dense; all the insights (or observations) seem to be what you can read in the (relatively short) wikipedia article. It is also not extremely entertaining.
I wonder whether it was a revealing, revolutionary book back in the days, or whether it is different to people with a certain background (or lack thereof), such that my impression is, in some sense, biased. I also wonder whether the other books by Taleb are better, but given the praise that FbR seems to have received, I guess it is not likely that the Black Swan would be fundamentally different from FbR.
I read Black Swan early in my introduction to heuristics and biases, in my teens. I remember that the book was quite illuminating for me, though I disliked Taleb's narcissism and his disrespect for the truth. I don't think it was so much "insightful" as helping me internalize a few big insights. The book's content definitely overlaps a lot with beginner rationality, so you might not find it worthwhile after all. I read a bit of FbR and about half of Antifragile as well, but I found those much less interesting.
An aside: Taleb talks about general topics. It'... (read more)