This essay examines the 1999 biographical drama film Boys Don’t Cry, which represents the story of Brandon Teena, a transman, who was brutally killed by transphobic violence in 1993 in Nebraska. The first half of this essay queries the idea of masculinity as performance by exploring the film’s portrayal of the transsexual protagonist's transgressive gender presentation. Paying attention to how the cinematic text presents Brandon’s masculine performance, my essay analyzes the film as a queer text in which an alternative masculinity is presented against hegemonic masculinity. I also address the film’s indictment of transphobia shared by heteronormative men and women. In the second of the essay, I investigate the film’s queer dogma, which dismisses the transsexual subject’s desire and identity as symptoms of homophobic homosexuality. By looking closely at the last part of the film in which Brandon is unambiguously represented as a lesbian, this essay discusses marginalization of transsexuality in queer studies. In doing so, I refer to Jay Prosser’s critique of Judith Butler’s notions of transgender and transsexual, and examine how Boys Don’t Cry re-inscribes such queer dogma. This essay concludes that the film is an ambivalent text oscillating between an expression of subversive queerness and repressive transphobia.