Hypermasculine character styles are commonly encountered in clinical practice, popular media imagery and, indeed, in everyday life. Such "hypermasculinity" is readily recognized as an exaggeration and distortion of traditionally masculine traits, and has been studied by Adler (1923), Freud (1937), Reich (1949), Ovesey (1969), and Stoller and Herdt (1982), among others. In this article, I will review those contributions and identify and elucidate two modal forms of hypermasculinity: the Man's Man and the Ladies' Man. I will argue that these two patterns constitute recognizable forms of character pathology with their own understandable developmental paradigms, intrapsychic conflicts and object ties. A developmentally based model for the evolution of hypermasculinity will be proposed, and the implications of these concepts explored.