This paper, divided into two parts – which will eventually form two separate, shorter chapters in a book manuscript I am working on – is an attempt to revise into a more accessible form one long, academically-toned chapter for a more popular audience. With a central focus on the University of Natal’s medical school, which was a leading training institution for aspirant African, Indian and Coloured doctors during the apartheid period, this manuscript aims to flesh out the complex history of black medical education, professionalisation and student politics in South Africa from roughly the 1940s to 1990s. This paper moves away from the institutional perspective of earlier chapters to explore some of the difficulties black students had to overcome to study medicine in Durban. In addition to an analysis of the personal and educational backgrounds of students that assisted and hindered their progress to medical school, Part I of this paper entitled “You are crying for the moon!” will consider what motivated students to study medicine. However, for the few who made it to Durban, many further hardships awaited them in pursuit of their medical careers. Part II entitled “One’s memories of medical school are full of ambivalence and contradictions” builds on from Part I by discussing some of the social and educational struggles of students once they gained admission to this medical school. The medical school’s anomalous set-up as a black faculty within the white University of Natal forced its students to suffer many hurtful and humiliating racial inequalities during the apartheid period.