Hair and hair care are psychologically meaningful for Black men. This article illuminates the stories of Black men as they negotiate their identities by having their hair cut by others, in and outside of the barbershop. Nineteen stories from 14 Black men were elicited from prompts using the Guided Hair Autobiography. The findings reveal varied and complex hair stories, with primary themes of paternal rituals, Black community belongingness, and hair care distress. The findings suggest that Black men’s hair care spaces and the roles played by those who cut hair can become emotionally harmful or offer entry points into greater self-understanding and psychological wellness for Black men. A hair-based psychological intervention—PsychoHairapy—is offered as a framework to address wellness for Black men.