This dissertation argues that Nella Larsen, Tess Slesinger, and Jane Bowles, in a set of novels published between 1928 and 1943, all deployed laughter—not humor or comedy, but laughter itself—to express a critique of the rigid prescription of female subjectivity. In a historical window of epistemic instability, between the earlier dominance of humanist individualism and the subsequent dominance of humanist universalism, these authors reacted against nominally liberatory political movements, such as first-wave feminism and Black “uplift,” that had not in fact challenged an ideal of the sovereign subject still modeled on the white male Euro-American individual. Their objections anticipated, by several decades, later critiques of the subject that emerged in second-wave feminism and post-structuralist theory. Laughter, as Larsen, Slesinger, and Bowles understood, reckons with difference, and not only identitarian difference: when we laugh, we recognize someone or something as different, other, and differently different, otherly other—not a defined other, but a fresh challenge to discursive taxonomy. Moreover, when we laugh, experiencing a material overthrow of subjective control, we encounter the otherness, the multiplicity, of the self ever different from itself. Laughter thus opens the self to difference, inside and out. But the “subversive” force of the laughter of the oppressed can also be coopted and reabsorbed by a dominant social order. This project takes up Zora Neale Hurston’s Their Eyes Were Watching God (1937) as a case study in the limits of the “subversive,” before turning to Larsen’s Quicksand (1928), Slesinger’s The Unpossessed (1934), and Bowles’ Two Serious Ladies (1943) as exemplars of a more radical laughing objection to the prescription of subjectivity, and to the dualisms that undergird the subject’s construction: self and other, oppression and resistance, mind and body, thought and feeling, depth and surface. The latter novels laugh a “laughter of the middle”: a materially situated, present laughter, living in the in-between spaces of dialectical discourse; a laughter of the here and now, the ever-shifting ground of a self in pieces.