Gay and bisexual men (GBM) have reported viewing significantly more sexually explicit media (SEM) than heterosexual men. There is some evidence that SEM depicting bareback anal sex may be linked to engagement in condomless anal sex (CAS) and thus HIV/STI transmission among GBM. A nationwide sample of HIV-negative GBM in the U.S. completed an online survey that included measures on SEM consumption (both overall frequency and percentage viewed depicting bareback sex) and reported on CAS in the past 3 months. Data showed that there was no main effect for the frequency of SEM watched in association on either the number of CAS acts with casual partners or the probability of engaging in CAS during a casual sex event. However, there was an interaction between amount of SEM consumed and percentage of bareback SEM consumed on both outcomes, such that men who reported both a high frequency of SEM consumption and a high percentage of their SEM being bareback reported the highest levels of risk behavior. These findings highlight the role that barebacking depicted in SEM may play in the normalization of sexual risk behaviors for GBM. Interventions looking to target the role SEM may play in the lives of GBM should examine what variables may help to mediate associations between viewing SEM and engaging in risk behavior.