If the ultimate purpose of critical engagement with black men and masculinities is the development of progressive masculinities, the growing body of scholarly, pedagogical and media-related work on men and masculinities in South Africa has reached a dead end – or something close to it. This article employs three media pieces as springboards to highlight the currency of the topicality of masculinity, but, crucially too, the apparent gaps in how black South African masculinities are thought of, in order to respond to how work on men and masculinities can negotiate itself out of the current impasse. While the article is anchored in the phenomenon of masculinity as a media headline issue, it is not an exhaustive analysis of the prevalent discourses of black masculinity conveyed by the media. The article argues that, in the context of the enduring power of monist theories and politics of men's and blacks’ lives, (re)engaging black and African feminisms for black men, alongside critical black thought, might be precisely what is needed to ‘make the black man come to himself’ as Biko put it, and towards liberating black masculinity.