Masochistic elements are puzzling entanglements for most of us in the beginning. Taking Melanie Klein's attempts to think about them thus show one way how to make sense of them. Starting from her struggles with masochistic symptoms in child analyses in the early 1920ies Melanie Klein tried to conceptualize those experiences in a way that could help to fact them in the analytic process. In this article the development is outlined, the move from thinking about them in libidinal terms to gradually grasping in greater depth their destructive quality. She speaks of an “evil principle” and then finds a conclusive solution in conceptualizing masochism as a representation of the death drive. In the next decades her followers would further work on the complexities of the countertransference issues and superego organizations in masochism in more detail as will be shown. Finally, a look in a piece of present analytic work will exemplify the clinical usefulness of the Kleinian conceptualization.