John Dewey was one of the greatest thinkers of Pragmatism, the American philosophy that attempted to re-balance the relationship between thinking and life. Although Dewey was not an aesthetician, his masterpiece Art as Experience (1934), derived from the revised version of his William James Lectures in 1931 at Harvard, won him fame in the field of aesthetics. Some experts consider it as one of the best English books on aesthetics. Prior to Art as Experience, Dewey had started to work on his aesthetic theory and an art theory in Experience and Nature, a book compiled from his Paul Carus Lectures in 1925.In order to have a comprehensive and accurate understanding of Dewey’s aesthetics, one should start with his metaphysics. Dewey noticed that there is no possibility to avoid thinking about metaphysics whenever a serious thinker encounters the question of ″being.″ But like another classic pragmatist Charles Peirce, Dewey was not a foundationalist. His standpoint of anti-foundationalism led him to a certain kind of inquiring metaphysics, which aimed to transcend both rationalism and empiricism, and to overcome traditional dualism. Dewey’s empirical naturalism was the theoretical result of this metaphysical inquiry, and it was via his empirical naturalism that Dewey further developed a theory of progress and a philosophy of wholeness. A better understanding of Dewey’s metaphysics of empirical naturalism makes it easier to understand his aesthetics. Dewey emphasized and focused on the continuity between art and everyday life. His definition of ″art″ showed that only when people interact with art products and engage in art activities, do true works of art come into being. That is to say, without human experience, art would not exist. Dewey’s concepts of ″an experience″ and ″aesthetic experience″ demonstrate the most consummate experience that makes it possible for art to provide meanings and values to human life. Dewey claimed that art and aesthetics are real ″intelligence″ essential for a good life, and true ″practice″ to give meanings to human beings. He considered art as the promise of the possibility of a consummate experience with which human beings can unite to pursue a real good life. A good life means an expressive, creative, free and intellectual life. For Dewey, art answered the question of ″what is the meaning of living.″ The greatest insight in Dewey’s aesthetics is the connection between art and democracy. Art, as open communication, fully realizes democracy. In other words, a democratic community enables a good life, and a democratic life is the ideal good life. Dewey noted that the philosophy of wholeness and the theory of process are the best ways to overcome dualism and foundationalism which are deeply bedded in traditional metaphysics. He also discussed the role of intelligence and emotion within the ideal ethical life. His discussion on ″meaning″ was the key point connecting his metaphysics and aesthetics, which resulted in an approach to the dimension of value in ethics. Hence, the conclusion of rediscovering Dewey’s aesthetics lies in two key terms: ethical experience and poetic meaning. Aesthetic experience arouses attention towards the ″presence″ and its situation, which is of highly moral value for human cultivation. In this sense, aesthetic experience is a sort of ethical experience, and art leads people back to life itself with a more profound understanding of life as a whole. Dewey’s end in view was to create a philosophy that directs the value theory for human beings, and reinforces their faith in the poetic meaning of existence, action, and creativity. Rethinking Dewey’s aesthetics today may illuminate us and bring us a broader vision of the future.