The present investigations applied a theoretical perspective regarding the impact of executive functioning (EF) on sexual risk among substance users, using a methodological approach designed to examine whether EF subtypes differentially predict behavior patterns. Participants included 104 substance-using HIV-negative gay and bisexual men. Participants completed 5 neuropsychological assessment tasks selected to tap discrete EF components, and these data were linked to data on substance dependence and behavioral reports of substance use and sexual risk in the past 30 days. Cluster analysis identified 3 EF subtypes: (a) high performing (good performance across all measures); (b) low performing (poor performance across all measures); and (c) poor IGT performance (impairment on the Iowa Gambling Task [IGT] and its variant, but good performance on all other tasks). The 3 subtypes did not differ in amount of substance use, but the low-performing subtype was associated with greater rates of substance dependence. The low-performing subtype reported the highest rates of sexual behavior and risk, while the poor-IGT-performance subtype reported the lowest rates of sexual risk taking. Global associations between substance use and sexual risk were strongest among the low-performing subtype, but event-level associations appeared strongest among individuals in the high-performing subtype. These data suggest complex associations between EF and sexual risk among substance users, and suggest that the relationship between substance use and sexual risk may vary by EF subtypes.