The growth of the black¹ middle class in ‘post-apartheid’² South Africa has become the subject of scholarly and public interest. Applying elements of discourse analysis to interview and group discussion based data, this article provides a qualitative thematic exploration of two pressures that confront a group of black middle-class professionals residing in Johannesburg, South Africa. The first pressure is the experience of being black under the hegemonic white gaze and the second is the experience of the marshalling black gaze. The complexities of occupying the positions of being black and middle class and of living with the scrutiny of two gazes concurrently, is explored. The findings suggest that the white gaze persists in seeking to negatively mark and destabilise black professionals and profiting off covert and paradoxical mobilisations of race discourses as a means of bolstering whiteness. On the other hand, the black gaze serves to police the boundaries of what acceptable blackness is. Under this gaze, the professional, black middle class is perceived as having sold out to whiteness and abandoned given conceptions of blackness. The tensions arising out of navigating these dialectical disciplining gazes suggests that this group holds the tenuous position of being corralled from the ‘outside’ and ‘inside.’ The research, however, reveals the complex ways in which racialisation continues to shape black lives alongside the less rigid identity possibilities for blackness that move beyond essentialised identity performances.