While scholars have analyzed the masculinity crisis portrayed in American fiction, few have focused on postmodernist fiction, few have examined masculinity without using feminist theory, and no articles propose an adequate solution for ending normative masculinity’s dominance. I examine the masculinity crisis as it is portrayed in two postmodernist novels, David Foster Wallace’s novel Infinite Jest and Chuck Palahniuk’s novel Fight Club. Both novels have male characters that ran the gamut of masculinities, but those that are the most successful at avoiding gender stereotypes (Donald Gately in Infinite Jest, and the narrator in Fight Club) develop a masculinity which incorporates strong, phallic masculinity and nurturing, testicular masculinity, creating a balanced gender. At the same time, both novels examine postmodernist fiction’s future. Post-postmodernist fiction, similar to well-rounded masculinity, seeks to be more emotionally open with the reader while still using irony and innovation for meaningful effects, not just to be clever.