The portrayal of gender in popular media such as music, movies, and TV series have grown in popularity the last few decades. Consequently, representation of gender has become more important than ever to examine. The American sitcom Friends is a popular media text which portrays six friends as they try to navigate life as young adults. Through the theoretical lenses of Butler, Connell, Kimmel, and others, this thesis sought to analyze whether the male characters on Friends portrayed toxic masculinity, and whether the show endorses this representation. The thesis found that all main male characters attempt to emulate hegemonic practices in various aspects of their lives, and it can be difficult to discern whether the show’s laugh track ridicules these attempts or endorses them. The men’s oppressive behavior is often framed as jokes and the laugh track is quick to remind the audience that their behavior is one to be ridiculed. Other times, the men negate certain aspects of hegemonic masculinity through intimacy, close friendship, and support, but here the laugh track also is often quick to shut this down as well. The ambivalence of the show makes it hard to discern exactly which aspects of hegemonic masculinity the audience is supposed to endorse, and which aspects should be criticized. The men’s behavior is not accidental since it creates the foundation for most of the show’s jokes. While each character embodies their own flavor of complicit masculinity, they also express greater empathy and vulnerability than what hegemonic masculinity would expect. The show aired in the 1990s and this thesis attempted to keep this in mind through the analysis though it recognizes that the sitcom received a backlash in 2018. The reason for this backlash is partially rooted in a shift in audience, and a shift in how the audience perceives hegemonic masculinity and how men treat each other and women. The thesis concluded that the show has representations of toxic masculinity, it attempts to criticize exactly those representations, and that the show did not seem to contain much competition between the men, something hegemonic masculinity would otherwise require. It suggested to investigate the representation of race on the show, as well as looking into its representation of the trans community which in both cases it was criticized for during its 2018 backlash.