Contrary to the widespread belief that rap music is a non- (or even anti-) sentimental artform, much of American hip hop culture draws on sentimental elements and aesthetics. In fact, politically charged hip hop productions often rely on popular sentimental tropes to thwart dehumanizing portrayals of marginalized groups – including gangsta rap. Notably, this encompasses works that critically engage with the US penal system: by casting the Black male prisoner as as a suffering child, such productions aim to elicit empathy from their audience. Apart from the depiction of the imprisoned individual’s own pain, the grieving mother – whose sorrow mainly stems from being separated from her incarcerated child – serves as a particularly popular motif. Against the broader theoretical backdrop of prison abolitionist theory, hip hop studies, and the study of affect and public feeling, this article examines sentimental elements in works by African American male hip hop artists. Primarily focusing on song lyrics and visual material by rappers 2Pac and YNW Melly, it argues that sentimental aesthetics are used not only to challenge the prison industrial complex, but also to counteract pathologizing notions of Black masculinity within the American cultural imaginary.