Abstract: On the overall aesthetic character, it is no exaggeration to say that the Chuang Tzu has influenced Chinese poetry artistic conception and literati painting artistic criterion more profoundly than any other single book.This is a common sense in academia.This dissertation tries to study the cognition of painting's funtion and literati painting's developing from form similitude to content in mind, then to interest, through which period literati play was born.After that, the paper analyzes the Chuang Tzu's influence on literati psychology throughout the whole art history.