In the late 1970s and early 1980s, Richard Rorty advocated that his confréres kick the ‘philosophy habit’-that is, adopt a post-positivist, post-metaphysical style of interpretation. Philosophers largely ignored Rorty’s clarion call. Unburdened by the kind of Selbstverständnis of scholarly mission held by most analytics, members of departments of literature instead became the most important advocates for reading literature philosophically during the last two decades of the twentieth century. Though the academic Left, especially practitioners of ‘theory’, largely celebrated and encouraged this development, Rorty, in the late 1990s, came to view it as harmfully elevating ‘cultural politics’ above ‘real politics’, which would ultimately lead to the abandonment of civic responsibilities. While heavy-handed and partial, Rorty’s critique of the uses of philosophy by literary critics was not only perceptive, but can be helpful for understanding how the contemporary academic Left might move forward as well.