This project focuses on the late-nineteenth and early twentieth century depictions of success and failure in prominent fiction and addresses how these concepts played a vital role in the construction of masculinity during that period. While I highlight how the idolization of popular fictional success narratives under American corporate capitalism served to standardize hegemonic forms of masculinity, I also detail how certain authors redefined failure in order to challenge standards of masculinity. I begin by considering how William Dean Howells uses ethical challenges to self-made manhood to challenge the meaning of male failure. In contrast, I argue that Frank Norris wanted to legitimize reactive male violence to stave off fears about failure; despite the fact that he clearly evolved in his thinking about violence throughout his career, his essential verdict about failure itself and the gender-bound obligation to avoid it did not change. I then turn to Jack London to examine the marked contrast between the depiction of success in his early writing career and his late career by examining two novels in each period. I assert that while the early London thought obtaining success was essential for obtaining a sense of meaning, his later novels did not retain the same trust in the popular conventions about success. I follow London by turning to Willa Cather, who, I argue, destablized popular conventions like success and failure through her construction of gender. Finally, I conclude by considering how popular, gender-bound conventions about success and failure still determine our narratives in television, film and fiction in different ways.