This analysis focuses on several masculinities conceptualized by Holden Caulfield within the sociohistorical context of the 1950s. When it is understood by heterosexual men that to be masculine means to be emotionally detached and viewing women as sexual objects, they help propagate the belief that expressions of femininity and non-hegemonic masculinities are abnormal behavior and something to be demonized and punished. I propose that Holden’s “craziness” is the result of there being no positive images of heteronormative masculinity and no alternative to the rigid and strictly enforced roles offered to boys as they enter manhood. I suggest that a paradigm shift is needed that starts by collectively recognizing our current forms of patriarchy as harmful to everyone, followed by a reevaluation of how gender is prescribed to youth