This chapter explores Heracles’ defeat of Cerberus. After providing a brief overview of Heracles’ presence—or rather absence—in the retellings of the Cerberus myth, it focuses on four ways in which the intricacies of the Labor are explored. Concentrating on the Homeric Iliad, the intertwining of Heracles’ Labor with the underworld journey of Theseus and Pirithous, the introduction to the myth of Heracles’ initiation into the Eleusinian Mysteries, and the Labor’s representation in Euripides’ Heracles, the chapter shows how the myth is a mechanism through which ancient mythmakers explore what it means to be a hero. Heracles—godlike and superhuman, mighty and outmoded, humanized and blessed—is seen through his conquering of Cerberus either as being precisely what more contemporary heroes should not be or as embodying the very contradictions and blurred boundaries that Cerberus’ defeat creates.