The article reads David Fincher’s Fight Club (1999) and Darren Aronofsky’s film The Wrestler (2008) as films that deploy masochistic spectacles of heroically suffering white men. Both Fincher and Aronofsky are well known for their dark and sometimes surreal films that frequently take up violence as a theme (Mayshark, 2007). They are also prominent auteurial voices, nominated for and winning multiple prominent film awards. Both Fincher and Aronofsky are, the article argues, representatives of a class of American directors who, starting in the early 1990s, made independent art house films and won accolades at various film festivals, making anti-mainstream, if not subversive cinema. These filmmakers of the 1990s sustained the spirit of enquiry that was the hallmark of the auteurs of the New Hollywood age. Our contention is that Fincher’s Fight Club and Aronofsky’s The Wrestler can be accommodated on this list as films made by subversive filmmakers and that they share common features owing to their commitment to explore constructions of masculinity and performances of the same. The question that the article seeks to address is—does David Savran’s framework offered in Taking it Like a Man: White Masculinity, Masochism, and Contemporary American Culture (1998) predict the distinct male posturing of masochistically suffering white men visible in Fight Club and The Wrestler? The article will primarily use the theoretical framework offered by David Savran to examine where Fight Club and The Wrestler are situated with respect to the mainstream Hollywood fare featuring hyper-masculine heroes. © 2015, © 2015 Mudra Institute of Communications, Ahmedabad, India.