This article considers whether mainstream Hollywood “bromance” movies offer potential for sex/gender transgression and/or progressive representations of masculinity. Bromances resemble the heavily feminized genre of romantic comedy (or “rom-coms”) except that the action centers on male friendships rather than heterosexual romance. On the surface, at least, bromances promise opportunities for gender subversion and seem to offer richly heterodoxical possibilities. Using The Hangover (2009), Wedding Crashers (2005), and I Love You, Man (2009) as examples of mainstream bromance, this article argues that while it is possible to observe crevices in the representation of monolithically heteronormative masculinity in each of these films, their subversive potential is decidedly limited. These limitations suggest that while considering heterodox masculinities in bromantic movies may be productive, heterodoxies are complex and, perhaps, even contradictory. While the concept of heterodoxy seems to have potentially exciting applications in masculinity studies, this articles argues for care and caution in its adoption.