Among the many elements in the thought of Bernard Lonergan, a twentieth-century Canadian Jesuit philosopher and theologian, one of the most important is his theory of authentic conversion. Lonergan himself subdivided this topic into intellectual, moral, and religious conversion, but his writings on the arts may also justify a further category, aesthetic conversion. The present essay demonstrates that all four elements of Lonerganian conversion, in diverse ways and in varying degrees, can be explored through the study of two classic works of literature: Shakespeare's The Winter's Tale and Dante's Purgatorio. Not only do the major characters in these texts undergo transformations, or conversions, that can be illuminated through Lonergan's concepts but, moreover, both texts as a whole use complex aesthetic methods to attempt a similar transformation in their readers. As such, from a Lonerganian standpoint, these works of literature both illuminate the meaning of authentic conversion and seek to enact its effects.