In the history of Chinese thought, Confucianism is often contrasted with Legalism in terms of the former’s emphasis on li (ritual or rite) and the latter’s emphasis on fa (laws). However, others have argued that the Confucian li have served some of the same purposes as laws in the Western world. This article shows that through an overlap between Dewey’s concept of custom and the Confucian notion of li, and Dewey’s understanding of the relationship between custom and law, Dewey’s pragmatism could engage Confucian philosophy on the key questions of what kind of tools will achieve good government. It argues that pragmatically rituals and laws are complementary tools of government, but the perceived differences between them reveal important insights regarding coercion and moral transformation in relation to good government. Dewey’s insistence that the rational and aesthetic should not be separated in any satisfactory experience provides the basis for an argument that the aesthetic emphasis of li complements the rational emphasis of laws, and a balance between the two is required to achieve Deweyan democracy as a way of life, in which aesthetic elements of culture will be as important as the rational structure of a political system.