Cultural criminology suggests that crime, deviance, and transgression are often subcultural in nature. For this reason, cultural criminologists often focus on the simultaneous forces of cultural inclusion and social exclusion when explaining criminal, deviant, or transgressive behaviors. This is a particularly useful bricolage for examining contemporary gay deviance and transgression—behaviors that are perhaps closely linked to (if not directly caused by) the past isolation, marginalization and/or oppression of homosexuals by Western heteronormative societies. It is also useful for understanding behaviors that are the result of marginalization and oppression from other sources, namely, the gay community itself. Using subcultural theories of deviance—such as those favored by cultural criminologists—this article explores a perspective that can be used for exploring certain forms of gay deviance and transgression. First, some of the more ostensible criminological theories that satisfy a prima facie criminological inquiry will be presented and critiqued: labeling and stigma, and resistance to heteronormativity. To these will be added a new and potentially productive way of thinking that takes into consideration rule-breaking as a form of resistance to homonormative norms, values and rules.