This is the first full-length philosophical study of the work of Stanley Cavell, best known for his seminal contributions to the fields of film studies, Shakespearian literary criticism, and the confluence of psychoanalysis and literary theory. It is not fully appreciated that Cavell's project originated in his interpretation of Austin's and Wittgenstein's ordinary-language philosophy and is given unity by an abiding concern with the nature and the varying cultural manifestations of the skeptical impulse in modernity. This book elucidates the essentially philosophical roots and trajectory of Cavell's work, traces its links with Romanticism and its recent turn toward a species of moral perfectionism associated with Thoreau and Emerson, and concludes with an assessment of its relations to liberal-democratic political theory, Christian religious thought, and feminist literary studies.