Self-labeling of, and preference for, anal sex roles is an important aspect of identities and cultures among men who have sex with men (MSM) populations. In this article, we examined sociodemographic and behavioral correlates of preference for and maintenance of anal sex roles, and risk for HIV infection. Using time-location sampling, we conducted a cross-sectional survey of racially diverse MSM in San Francisco. Of the 386 men who reported an anal sex role preference, 41% preferred being "versatile" while 21 and 37% preferred being "bottom" and "top" only. Lower educated men, Asian/Pacific Islander men, and men born in Asia/Philippines were more likely to prefer being "bottom." Among all racial/ethnic groups, men in general did not maintain their preferences 100% of the time in their reported sexual behavior, and none of the racial/ethnic groups maintained their preference at greater or lesser levels than any other group. There were no significant differences in all the behavioral risks between men who maintained their preferences and those who did not. Yet, prevalence of HIV infection was two times higher among men who were strictly "bottom." Linguistically and/or culturally appropriate HIV prevention information/interventions at an appropriate educational level should be provided to those from the developing world and those of lower socioeconomic status, who may lack the knowledge of differential risks associated with anal sex activities.