||Building on Sianne Ngai's recent work on affect theory, this thesis explores the intersection of negative affect and critical punishment in four social climbing narratives of the early 20th century: Edith Wharton's The Custom of the Country (1913), Anita Loos's Gentlemen Prefer Blondes (1925), and Nella Larsen's Quicksand (1928) and Passing (1929). The novels share structural elements and cultural concerns, using physical mobility as a metonymic representation of social mobility. The protagonists' spiraling journeys illustrate structural paradigms of narrative punishment that reveal a deep cultural anxiety about young women's relationships to class and labor. Critical evaluations of the novels replicate this anxiety, not only at the time of initial publication but even today. Drawing on this body of commentary as well as biographical information and archival research, this thesis examines the contradictions between these harsh critical responses and the authors' own understandings of their characters. I argue that separate from, and often in direct contradiction to, the authors' statements about their protagonists, the various forms of negative affect at work in the texts encourage critics to continue to "punish" these social-climbing women. Of the affects Ngai attends to, this project will specifically examine envy, irritation, and "a strange amalgamation of shock and boredom" that she calls "stuplimity." Honing in on a 15-year period that produced four strikingly similar novels by female authors, I demonstrate that it is significant that these texts emerge at a time in American literary history when criticism itself was concerned with a hierarchical valuation of the literary marketplace on a massive scale.