Female-to-Male cross-dressers have a notable history in Iranian cinema, rising during reform eras. The films deploy unique cultural tropes and speak to larger changes in society. While Male-to-Female cross-dressing characters are usually associated with comedic entertainment, criminality, and trickery, Female-to-Male cross-dressers are typically coerced into adapting to another gender identity, often as an act of necessity to gain employment. The films champion women’s rights and problematize the constructs of masculinity. Moreover, given that men have more rights and authority, posing as a man is socially understandable. In this paper, I will compare two popular films from the reform decade of Pahlavi’s “White Revolution”—The Champion of Champions (1965) and Shamsi Pahlevoon (1966)—with two award-winning films from the reform era of Mohammad Khatami’s presidency—Daughters of the Sun (2000) and Baran (2001). I will show how these films mimic two distinct masculine archetypes—jahel and amrad—to expose the strictures of tradition as well as the repression experienced under the patriarchal and class barriers of their transformative times. Before the revolution, female characters changed into the archetypal tough guy (jahel) from the commercial cinema. They don a mustache, a velvet hat, a black suit, and white shirt while speaking and behaving as a macho. In these comedies, the Female-to-Male characters are exaggerated, satirizing masculine identity. They not only transgress gender but also class. They foreground the force of modernity by becoming active agents and pursuing desired partners. Ultimately, these characters return to more passive female roles—reestablishing the primacy of the heteronormative identity. The films end happily with what Afsaneh Najmabadi has called the “marriage imperative” in Iranian society. In post-revolution cinema, crude jahels are no longer permissible role models. The most common Female-to-Male character is derived from the known figure in Persian culture of the amrad, the sensitive young man without facial hair who is beautiful, androgynous, and quiet. Masculinity is not satirized by exaggeration but feminized. This passing character also recalls the idolized self-sacrificing innocent martyr of the Iran-Iraq War. The plight of women and the poor are highlighted in these critical dramas that call for social justice. Yet there are no happy endings, even if the characters return to their female roles. In much the manner of classical Persian poetry, love triggers a character’s internal awakening, but is not consummated.