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Hard to know where to start. The first anarchist? Yang predates Zhuangzi, but none of Yang's works survive. The first post-rationalist? Zhuangzi's dialogues with Huizi hint at this in how Zhuang dissects Hui's doctrines...but Hui's doctrines are mostly lost, too.
The first troll? Well, Diogenes was about 40 years older. Still, Zhuang stands out among a notoriously dour lot.

The Zhuangzi is half-brilliant and half-indecipherable, because Zhuang existed in a discourse community that was mostly wiped out. He critiqued (and mocked)...
...schools we know basically nothing about any more. So if you want to study Zhuang, expect to be confused by a lot of it. Fortunately, Zhuang didn't go in for grand theories, piling one terminological brick on another. Instead, you can read his chapters independently.
You can think of each part of each chapter as a puzzle. Some will make sense now, some will make sense later, some won't make sense at all. That's OK. There's a direct line of influence from the Zhuangzi to Zen koan practice, though Zhuang never heard of Buddha.
The easiest introduction to Zhuangzi, IMO, is CC Tsai's manhua (cartoon) version. (My avi is Tsai's version of Zhuangzi.) It's abridged and I think gets some things wrong, or at least needlessly confused, but the spirit is there. amazon.com/Nature-Illustr…
My favorite text translation is Nina Correa's: daoisopen.com/ZhuangziChuang…

Chad Hansen has written an excellent survey of Zhuangzi with particular attention to questions of language: plato.stanford.edu/entries/zhuang…

A much less respectable take by Hakim Bey: hinessight.blogs.com/church_of_the_…
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