This paper describes the historical background to contemporary discussions of empathy and rationality. It looks at the philosophy of mind and its implications for action explanation and the philosophy of history. In the nineteenth century, the concept of empathy became prominent within philosophical aesthetics, from where it was extended to describe the way we grasp other minds. This idea of empathy as a way of understanding others echoed through later accounts of historical understanding as involving re-enactment, noticeably that of R. G. Collingwood. For much of the late twentieth century, philosophers of history generally neglected questions about action explanation. In the philosophy of mind, however, Donald Davidson inspired widespread discussions of the role of folk psychology and rationality in mental causation and the explanation of actions, and some philosophers of history drew on his ideas to reconsider issues related to empathy. Today, philosophers inspired by the discovery of mirror neurons and the theory of mind debate between theory theorists and simulation theorists are again making the concept of empathy central to philosophical analyses of action explanation and to historical understanding.