In this chapter, the author presents an overview of his psychoanalytic understanding of masculinity and male development. He provides what his mean by phallic and genital masculinity and addresses the roles played by both biology and culture in influencing how boys establish their earliest sense of masculinity. The author focuses on the internalisation processes impacting masculine gender identity prior to reflecting upon the interplay between the male's initial sense of masculinity, his uniquely gendered ego ideal, and the central developmental challenges that ensue in reworking the phallic and genital positions. He offers a contemporary perspective on gender. Though probably obvious, the landscape of psychoanalysis and gender abounds with conceptual, terminological, technical, and socio-political difficulties. Psychoanalysts are more likely to understand that gender identity development is not a linear, continuous trajectory, and that a boy's experience of the ambiguities of his gender is continually being reworked across differing developmental junctions.