Over the course of the past century, the dominant psychoanalytic paradigm for understanding boyhood and male gender identity development has been grounded in two complementary visions: Freud’s original formulations and, later, the propositions of Ralph Greenson and Robert Stoller. Each of those visions, history suggests, contain a certain harshness, rigidity, and fixity about gender roles and can even be seen as supporting an unhealthy bifurcation between male and female. In the last generation of psychoanalytic scholarship, a viable alternative vision about boyhood and “boys becoming men”—what I term the “post-structuralist psychoanalytic view”—has emerged and increasingly gained structure, definition, and traction. In this paper, I identify some of the important elements of that evolving vision (still very much a work in progress), review briefly three robust areas of current post-structural focus, and consider some of the differences between past and present conceptualizations. While not ignoring pathology and dysfunction, the post-structural psychoanalytic vision also gives voice to health and function, variation and differentiation, creation and construction, and “more life”; it can be seen as a reclamation of the positive and a celebration of the infinite hope, promise, and possibility of all that is boys and boyhood.