H. Lawrence Freeman's “Negro Jazz Grand Opera,” Voodoo, was premiered in 1928 in Manhattan's Broadway district. Its reception bespoke competing, racially charged values that underpinned the idea of the “modern” in the 1920s. The white press critiqued the opera for its allegedly anxiety-ridden indebtedness to nineteenth-century European conventions, while the black press hailed it as the pathbreaking work of a “pioneer composer.” Taking the reception history of Voodoo as a starting point, this article shows how Freeman's lifelong project, the creation of what he would call “Negro Grand Opera,” mediated between disparate and sometimes apparently irreconcilable figurations of the modern that spanned the late nineteenth century through the interwar years: Wagnerism, uplift ideology, primitivism, and popular music (including, but not limited to, jazz). I focus on Freeman's inheritance of a worldview that could be called progressivist, evolutionist, or, to borrow a term from Wilson Moses, civilizationist. I then trace the complex relationship between this mode of imagining modernity and subsequent versions of modernism that Freeman engaged with during the first decades of the twentieth century. Through readings of Freeman's aesthetic manifestos and his stylistically syncretic musical corpus I show how ideas about race inflected the process by which the qualitatively modern slips out of joint with temporal modernity. The most substantial musical analysis examines leitmotivic transformations that play out across Freeman's jazz opera American Romance (1924–29): lions become subways; Mississippi becomes New York; and jazz, like modernity itself, keeps metamorphosing. A concluding section considers a broader set of questions concerning the historiography of modernism and modernity.