The purpose of our article is to explore the relationship between masculinities and crime within the hip-hop (HH) and electronic dance music (EDM) nightclub scenes in Philadelphia. Given extant theory and research showing gender is a situated performance, the social context of the nightclub setting offers an important opportunity to contribute to the ever-growing masculinities and crime literature because it is an understudied setting populated by atypical offenders. Direct observation of 33 club events and interviews with 24 male clubbers yielded three important patterns: (a) Men with consistently high masculinities (hypermasculine types) reported the most frequent involvement in nightclub crime, (b) men with consistently low masculinity scores reported the least involvement, and (c) men with variable masculinity scores put on a more hypermasculine identity while clubbing, leading them to engage in nightclub crime. Contextual factors, such as excessive alcohol use, heightened sexuality, competitiveness, and commercialism, explain this more nuanced relationship between masculinity and crime. Abstract published by arrangement with Sage Journals.