Objectives. We investigated trends in, and predictors of, unprotected anal intercourse (UAI) with casual male partners of gay, bisexual, and other men who have sex with men (GBMSM). Methods. We analyzed data from cross-sectional intercept surveys conducted annually (2003-2008) at 2 large lesbian, gay, and bisexual community events in New York City. Survey data covered GBMSM's highest-risk behaviors for HIV acquisition (HIV-negative or unknown status GBMSM, any UAI) and transmission (HIV-positive GBMSM, any serodiscordant unprotected UAI). Results. Across years, 32.3% to 51.5% of the HIV-negative or unknown status men endorsed any UAI, and 36.9% to 52.9% of the HIV-positive men endorsed serodiscordant UAI. We observed a few statistically significant fluctuations in engagement in high-risk behavior. However, these do not appear to constitute meaningful trends. Similarly, in some years, one or another demographic predictor of UAI was significant. Across years, however, no reliable pattern emerged. Conclusions. A significant proportion of urban GBMSM engage in high-risk sex, regardless of serostatus. No consistent demographic predictors emerged, implying a need for broad-based interventions that target all GBMSM.