In a 1961 interview with the journalist Studs Terkel, James Baldwin offered a riveting assessment of Bessie Smith’s “Backwater Blues.” “It’s a fantastic kind of understatement,” Baldwin tells Terkel. “It’s the way I want to write.” Baldwin hears something in Bessie, a sonic and discursive quality he aspires to and identifies as “fantastic.” This essay considers the speculative undertones of Bessie’s blues and Baldwin’s literary realism. I argue that Bessie’s doubled vocalization in “Backwater Blues” lyrically declares her immobility and circumscription, while tonally staging freedom and boundlessness. Baldwin is drawn to this dual orientation and enunciation, a vocalization that in its iteration of the real transcends the social, spatial, and imaginative limitations of that order. If we read “Sonny’s Blues” the way Baldwin hears Bessie, as a fantastic kind of understatement, we discern subtle sonic and spatial iterations of the irreal. Attending to microtonal sounds in “Sonny’s Blues”—screams, whistling, jukeboxes—I show that the speculative emerges in Baldwin’s story when the sonic overrides the racialized inscription of space.