The objective of this article was to examine drug and sexual risk in four salient groups of men who have sex with men (MSM) in New York City (NYC): (1) nonhomeless young MSM (YMSM), (2) homeless YMSM, (3) adult MSM Speed users, and (4) HIV-positive "POZ Party" MSM. Lifetime and current exposure to drugs, drug injection, and selected drug-sex interactions are highlighted in each group. Data derive from recently completed field-based, ethnoepidemiological studies that used venue-oriented/targeted sampling and semistructured interviews. Across all four groups, findings show that both drug and sexual risk remain prevalent in the MSM population in NYC. This is especially troubling given the already high background prevalence of HIV and other sexually transmitted diseases in NYC and the widespread suffering and death already wrought by HIV/AIDS among MSM. These findings suggest that available public health interventions today are, in many respects, failing to reach, engage, and affect critical risk groups within the NYC MSM population.