Writing in 2004, bell hooks suggests that Black men respond to histories of patriarchal domination and emotional isolation through a “politics of cool.” She ties the notion of cool to the ability to be “real.” For her this is epitomized by the vulnerability of blues and jazz musicians whose art was historically a form of lament. She contrasts this with the versions of rap and hip-hop that, she says, use “cool” to distance men from their feelings. Whether empowering or a form of further disenfranchisement, the strategies of cool are the subject of this article. It asks how the politics of cool intersects with race and gender. The article considers the epistemology of “cool” across different consumer media. The music video, This Is America, it is argued, resists easy classification but expands the concept of and jouissance of ‘cool’ so that violence too becomes a kind of vulnerability, an expression of pain. The art of Mohau Modisakeng likewise pulls the politics of cool into the gallery and creates new possibilities for the sublimation of righteous anger. Through iterations of cool, Black masculine subjectivities are discussed as in tension with the dream of decolonization and the transnational reality of capitalization.