In the middle of the 20th century, while recovering from WWII and the 1953 Coup, Iranian society was gripped in a stranglehold of occupation and semi-colonialism. During this extended upheaval, influential clerics, leftist organizations and the State worked to reconfigure hegemonic masculinity in relation to the State’s modernization project, the "Persio-Islamic" identity’s relationship to the “West”, and leftist discourse. Each front presented its version as the only legitimate form of masculinity and femininity. For each, the goal was neither to dismantle the existing patriarchy, nor to create gender equality, but to acquire or maintain power. Drawing upon Gramsci’s hegemonic framework, Connell’s masculinities studies and feminist studies, this paper illustrates how Jalal Al-e Ahmad’s irreverently detailed stories, autobiographical sketches and letters, expose the ruptures of gender hegemony. By narrating the vulnerability and violence of hegemonic masculinity as well as the complicated agency in the context of emphasized femininity, Al-e Ahmad’s writings reveal the struggles inherent in the re-negotiations of Iranian-Islamic Selves and the inconsistencies of the gender hegemony produced by leftist, religious, and state discourses. In 'The School Principal,' Al-e Ahmad recounts his year as principal, where he encounters a diverse group of struggling male teachers and, in the end, resigns after publicly beating up a student “accused” of homosexual acts. In 'Samanu-Cooking,' Al-Ahmad shares a memory, most likely from his childhood, where women gathered for a Samanu-cooking ceremony lament over their complicated lives and the devious acts of survival. Scholarship has established the deployment of gender and sexuality as tools of Iranian state building or resistance. Given Al-e Ahmad’s role as an organic intellectual, his writings– especially Gharbzadegi/Westoxification (1962)– have also been analyzed regarding their influence on the 1979 Revolution and the Islamic Republic’s efforts to push gender and sexuality back into private spheres. However, few scholars have analyzed the impact of Al-e Ahmad’s uninhibited narrations and personal letters on Pahlavi era hegemonic masculinity and emphasized femininity. The false binary of Western/Eastern masculinity and femininity continue to persist despite the dangerous consequences of such divisions. It behooves us to re-examine the writings of Jalal Al-Ahmad who continues to be both lionized and condemned for his influence on “Eastern/Islamic” identity. By mapping out such ruptures, this paper takes another step toward dispelling the static presentation of masculinity/femininity.