This essay updates Aaron Smuts', 2009 Philosophy Compass piece, “Art and Negative Affect” in light of recent work on the topic. The “paradox of painful art” is the general problem of how it is possible to enjoy or value experiences of art that involve painful emotions. It encompasses both the paradox of tragedy and the paradox of horror. Section lays out a taxonomy of solutions to the paradox of painful art and argues that we should opt for a pluralistic approach rather than seeking a unified solution. Section surveys recent work on the topic, with an emphasis on views holding that it is possible for an experience of art to be pleasant partly in virtue of involving painful emotion. Section suggests a range of phenomena that are not usually considered under the umbrella of the paradox of painful art but that offer promising directions for further research.