In this article, the author discusses the benefits of using psychodynamic theory in researching black masculinities of adolescent boys in Alexandra Township, South Africa. Both individual interviews and focus groups were conducted with thirty-two adolescent boys, aged thirteen to eighteen years. These boys were provided with disposable cameras to take twenty-seven photos under the theme "my life as a boy" in the new South Africa. Arrangements were made for photos to be collected and processed. In the individual interviews, the participants were asked to give a description of each photo and why and how they had decided to take that photo to represent aspects of their masculine identities. Group interviews were also conducted in which the participants were asked to select five photos that best described their masculinities. Follow-up interviews were also conducted with four boys who were conforming and another four boys who were rejecting traditional notions of masculinity. In analyzing the data, the researcher used Frosh and Emerson’s (2005) psychodynamic-informed discursive interpretive framework to analyze feelings of ambivalence, hesitations, and contradictions revealed in the spoken texts about hegemonic and non-hegemonic masculinities. In addition, the attention in the analysis was paid to the researcher’s countertransference reactions to understand emotional concerns and tensions of being an adolescent black boy living in a township context. In conclusion, it is recommended that safe spaces should be created for adolescent boys to reflect on the subjective meanings, feelings, and emotions of what it means to be a boy in the new South Africa. It is argued in this article that psychodynamic theory has an important value in informing such community-based interventions.