In this chapter, I deal with Lipps’s most famous field of investigation, his theory of empathy. I provide a comprehensive and systematic analysis of a topic that, although widely popularized today, has only been superficially explored in the scholarship. I begin by addressing the question of the definition and general features of Lippsian empathy, highlighting how, in Lipps’s “canonical” conception, empathy is a psychological function that encompasses all manifestations of social cognition. Then, I discuss the evolution of Lipps’s empathology and the four stages it went through between the early 1880s and early 1910s. Moreover, I analyze how Lipps envisions the psychological underpinnings of the empathetic function while commenting on the three “basic oppositions” that, in his view, are inherent in the empathetic function (“practical” vs. “aesthetic” empathy, “basic” vs. “full” empathy, “positive” vs. “negative” empathy). I also discuss the crucial issue of the functional typology of empathetic processes and review in detail the seven types of empathy identified by Lipps in his mature and late writings. Finally, I show that, while considering empathy as a source of irrationality, Lipps also sees in it a privileged gateway to the theoretical forms of knowledge.