In the U.S., Black childhood has been underimagined. The representational vocabulary of Black childhood is fraught with dehumanizing and adultifying imagery and sounds—from representations of “Topsy” and “Black Sambo” to caricatures of pickaninnies and their many (re)iterations in U.S. popular culture. Popular music is one expressive domain wherein artists and audiences alike have contested and reinforced the peculiar adultification and infantilization that have long haunted Black American life. In the years surrounding the Trump presidency, numerous Black popular music artists made childhood a primary feature of their artistic output through vocal technique, lyrical content, merchandise, music videos, social media, and more. At the precise moment when white innocence was wielded most violently and obviously on the national stage, these artists challenged the assumed goodness and whiteness of innocence and its relation to childhood, performing capacious versions of free Black childhoods to various ends. This dissertation turns to the performance of childhood as a productive domain of inquiry and focuses on four artists/groups—Tank and the Bangas, Chance the Rapper, Jamila Woods, and Noname—all of whom chart a liberatory politics of Black childhood through sound. Through the poetics and aesthetics of their work, I theorize and historicize four interrelated, childhood-adjacent concepts: nostalgia, vulnerability, innocence, and freedom. Methodologically, I attempt to turn the tables on how vulnerability has normally been rendered in ethnographies. I blend (auto)ethnography about my own experiences as a white father of a multi-racial child with critical theory to analyze live and mediated performances of popular music. I look to music as a poetic and aesthetic space with which to not only grapple with the realities faced by Black children in the United States, but also to affirm Black childhood as a space of freedom, play, possibility, and joy. Ultimately, I make two interrelated assertions: (1) foregrounding Black childhood in our social analysis urges the necessity of abolition and (2) popular music is a primary conduit through which we can imagine an abolitionist future free of police, prisons, and the carceral logics that undergird their imagined necessity.