Despite its seemingly 'wrong-headed' relationship, Bakhtin's writings on carnival have much to offer democracy and education. We argue in this article for the potential of the carnivalesque to promote creative engagement with, and opposition to, contemporary systems and ideas. First, we comment on the significance of the carnivalesque for our current historical moment. Then, we explore how Bakhtin's writings on carnival relate to images of and hopes for democracy, followed by a discussion of the carnivalesque and education. We close with brief introductions of the articles that make up this special issue and set the scene for more delightfully 'wrong-headed' encounters.