This chapter explores Jay-Z’s 2017 visual album 4:44 and finds that the aesthetic stylings of 4:44 create a conduit through which students can understand the black femme(inist) theoretical structures that animate afropessimism’s critique, and further, through which students can learn to interrogate afropessimism’s presumed singularity, insofar as it is a black femme(inist) project. It elaborates how Jay-Z’s contradictions are especially generative for contextualizing afropessimism’s critique of liberal humanism as an appropriation of black femme(inist) scholarship. Specifically, 4:44 can be used to impress afropessimism’s black femme(inism)s’ critique of who does and does not matters, of how those lives have come to matter, and of how lives that don’t matter generate social life, not despite humanist odds, but in/as/through these odds.