Afro-Dominican singer-songwriter Xiomara Fortuna has enjoyed a career that spanned more than four decades and shaped the work of a new generation of Dominican musicians. In March 2017 she was bestowed a presidential award of honor and she accepted it barefoot, making a clear statement about her values and where she sees herself fitting in Dominican society. Drawn from three separate interviews conducted with Fortuna in Santo Domingo in July 2016, augmented by her extensive internet archive, this article frames a transcribed and translated testimonio that captures some of Fortuna’s experiences while coming of age in the Dominican Republic in the late twentieth century. While much of Dominican society’s African cultural history has been actively obscured by the ruling class, Fortuna has long celebrated Afro-Dominican culture through her life’s work and her identity has shaped how she has navigated a neoliberal society as a black artist. Her insights provide an essential piece of Dominican historiography that includes Dominican youth organizing on the Left in the 1980s and 1990s, feminist activism, and cultural production.