Ludwig Wittgenstein said, “A serious and good philosophical work could be written consisting entirely of jokes."
If this is true, then the Chuangzu is the definitive example. The book is full of humor, the authors argue, and this humor is not merely ornamental but fundamental to its philosophic purpose. Drawing on the philosophy of humor-- including insights from Freud, Kant, Bakhtin and others-- the authors show how the Chuangzu uses incongruence, the carnivalesque, the grotesque, for parody, satire, etc.
This is the book's greatest strength: it not only points out the rather obvious fact of the book's cheekiness, but fully integrates the book's humor into a larger philosophic project.
That philosophic project is to undermine or challenge the Confucian value of "sincerity"-- by which is meant a correspondence between one's roles/names/duties and who one actually or characteristically is (which is to say, a correspondence between names and forms). This project of sincerity is at the heart of Confucius' "rectification of names." For the Daoist (for Chuangzu), this project is doomed from the start because it demands that we "sincerely" adopt as real/natural/normative what is actually socially constructed. The Confucian project of sincerity thereby paradoxically creates hypocrisy, obsessions, stress, and all sorts of other ills.
The Chuangzu thereby employs a whole host of humorous techniques to lampoon and undermine the very idea of Confucian sincerity.
But the goal of the Chuangzu is not to replace Confucian false sincerity with a Daoist true sincerity. It's also not the goal (though many contemporary interpreters assume it is) to replace Confucian "sincerity" with Dapist "authenticity". (The difference between these two seemingly similar terms, described first by Trilling, is that sincerity is public-facing and socially responsible [I.e. to be sincere means to truly be who one projects oneself to be to the public; to truly be, in character, who the social public has assigned one to be, and who one pretends to be in front of that social public] whereas authenticity is inward-facing and private [I.e. one is "true" to one's actual core self, in the face of social pressures to be otherwise]). Instead of "authenticity," the Chuangzu encourages what the authors call "genuine pretending." If authenticity means being true to one's self, "genuine pretending" means that one has no "true" self-- one is entirely empty of some solid, individual core-- and that one can therefore "play at" any and every role without identifying one's self with any role.
This is the spirit of (child's) play, and it is th only way to survive in a hostile world that will conscript you into its violent purposes, try its darnedest to impose a "face" (a fixed social identity) on you, rob you of your freedom, etc. The arch-metaphor for "genuine pretending" is the Joker card: funny and ironic, the card can temporarily assume any value in any particular game, without permanently adopting that value-- it goes back into the deck the same Joker it was before it was drawn. The Joker is the great and flexible opportunist-- the ultimate trump card.
The Chuangtzu is one of my favorite books of all time, and I really enjoyed this accessible academic book!