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The Tao Te Ching and Chuang Tzu (aka the Laozi and Zhangzi) are the best places to start. Avoid Stephen Mitchell's Tao Te Ching and Timothy Leary's and Witter Bynner's and Aleister Crowley's -- almost any other is fine.
Victor Mair, Ursula LeGuin, and Robert Henricks are very good TTC's. Don't know of a bad Chuang Tzu but it's uneven, a collection cobbled together over many years -- Thomas Merton's abridgement is probably the best, he's very judicious in choosing and gives an excellent rendering.

Taoism (Daoism) is extremely intellectual, but it's very anti-pomposity and rigidity. I see it as primarily an epistemological critique of language, and of the limits of rationality as a tool for apprehending reality. As Zen Buddhists say, words are a finger pointing at the moon. Stop staring at the finger.
For discussion of Daoism, I highly recommend the blog Bao Pu[1] by Scott Barnwell. Or if you'd like to see a discussion of how the theory is applied in practical life, you might enjoy my book "The Tao of Chip Kelly" where I discuss the work of a unique NFL coach in Daoist terms.

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