Many of the most popular genres of narrative art are designed to elicit negative emotions: emotions that are experienced as painful or involving some degree of pain, which people generally avoid in their daily lives. Traditionally, the question of why people seek out such experiences of painful art has been presented as the paradox of tragedy, and recently Noel Carroll has spun off a related problem known as the "paradox of horror." In this article, the author aims to introduce a problem which he calls the "paradox of painful art" and to assess whether any of the existing accounts of the paradox of tragedy provide a solution to the paradox of painful art. The paradox of painful art can be stated as follows: (1) People do not seek out situations that arouse painful emotions; (2) People have painful emotions in response to some art; and (3) People seek out art that they know will arouse painful emotions. In the process of looking for resolutions to this paradox, the author examines theories designed to solve more particular problems, primarily those that try to explain the appeal of a particular genre. He attempts to establish a basic assumption that there is something similar going on in many different genres and forms of art that needs to be accounted for. After assessing the merits of several leading solutions to the paradox, he sketches a general explanation that can account for a wide array of the art experiences in question. (Contains 29 notes.)