It's got the goods: This is my second Alan Watts book and I enjoyed it very much. I noticed a reviewer stating that it seemed a little dry, of courses this is personal preference. For me, it started of good, dragged a little during the history of Zen part about half way through the first part, then the second part really picked up again. Again, that's only because I wasn't as interested in the background as in the practices. Someone who is interested in where it came from and the branches of Zen would find it very fascinating.
One of the fascinating things about reading The Way of Zen and The Book is that one can see many things that have transpired in our culture that were obviously influenced by Watts' philosophy. It can be seen as coming directly from his words and not just from another source.
Years ago I read Psyco-Cybernetics by Maxwell Maltz, and I agree that it is a classic written in the early 60's dealing with human behavior, self esteem and self image. After reading The Way of Zen, which was written in the 50's, it became apparent as to where many of Maltz's ideas came from, he just reorganized them and obscured any relation to Zen, just from a psychological point of view, which is good. I reading about the Zen way and didn't realize it. Since reading Maltz, I've read some about Zen and noticed the similarities, but reading this, one could almost accuse Maltz of plagiarism. The only thing is Maltz made it more palatable for the western mind that wasn't ready or willing to embrace eastern philosophy.
Watts' writing seems to be from the perspective of a philosopher rather than a practitioner. You get the idea that he believes in the validity of what the practice of Zen, but not that he was on the path himself, which takes nothing away from the book.
The Way of Zen didn't seem to be as dated as The Book, as his way of writing didn't really reflect any of the verbiage of the time.
It's really nice discovering these books that were written before "I was born" and seeing that they contain fresh insight to ideas that were around long, long before "I was born".
If you're into Zen, on a path to "Self" discovery, or just starting, this book has some good pointers.

A very difficult book. Alan Watts is clearly convinced that Zen is a great truth and superior in many ways to western thought, but he is not convincing. Much of the problem is tendentiousness. Western thought is said to be limited by mind body dualism, and Zen liberated by using the ""peripheral vision of the mind"" to grasp essential truths about existence. But is western thought limited by the envisioning of a world separate from the self, or emboldened to manipulate that world rather than allowing it to simply exist? The historical summary of thought is confusing, and the repetition of the koans of Zen teaching simply mysterious. Is it really useful to have sitting meditation when monks are beaten to stay awake, or is it, as Watts admits, a response to the constraints of oriental politeness? I plan to revisit this book another time, since the simplicity of the doctrine and its lack of a god-centered view of reality is appealing, but I have not yet been able to separate the sensation of satori from terminal boredom. ( )

A very good historical overview of the development of Zen Buddhism. It is not so much a description of beliefs and practices for someone who wishes to practice Zen Buddhism as it is a scholarly description of thos beliefs and practices. So if you are looking for a handbook to Zen, look elsewhere. But if you are interested in the place of Zen in the history of other forms of Buddhism, this is an excellent, readable study. ( )

I'm not a huge Watts fan - usually too esoteric for me. But this is a great introduction into Eastern Philosophy. He discusses several major currents in Eastern religious philosophy - from Taoism, Hinduism, the different 'brands' of Buddhism to finally Zen. What I found astonishing about the book is that it does not merely explain - or not explain - but rather give a feeling of what Zen is all about - in true Zen fashion. I keep rereading this one, just to remind myself of its profound insights. ( )

As another reviewer quotes Watts:

". . . . [T]he course of our thinking and of our very history has seriously undermined the common-sense assumptions which lie at the roots of our social conventions and institutions. Familiar concepts of space, time, motion, and of natural law, of history and social change, and of human personality itself have dissolved, and we find ourselves adrift without landmarks in a universe which more and more resembles the Buddhist principle of the "Great Void". . . ."

An odd criticism, as that is precisely what he urges. Alas, he doesn't grasp the meaning of the "Great Void" (if that's even a concept from Buddhism).

And again:

". . . . This is why, I think, there is so much interest in a culturally productive way of life which, for some 1500 (sic) years, has felt thoroughly at home in "the Void", and which not only feels no terror for it but rather a positive delight."

Umm . . . try 2,500 years, Alan.

Another reviewer suggests that Watts sounds a bit of a snob, which is "un-Zen-like". Nah. It's his ego, which his superior knowledge teaches one is to eliminate.