Until recently, the Viagra connection to HIV was anchored in older adults. However, CDC investigation showed stability in 50+ HIV diagnoses on the heels of upward trends in risk indicators among men who have sex with men (MSM) and substance abusing populations. Signs have increasingly pointed to recreational drug use among younger populations, to which Viagra is being added to the mix. Currently, the field is still locating the substance abuse, sexual risk and age-related dimensions of Viagra misuse. Recent studies identify it primarily as substance abuse, but the majority reports a combination of risky sex and risky drug use. At the very least, Viagra appears related to the enhancement of sexual experience or performance, even when it is used to compensate for erectile dysfunction caused by other drugs-either illicit or prescribed (e.g., antidepressants and highly active antiretroviral therapy or HAART). The populations studied, however, frequently have limited the generalizability of findings. This report analyzes the relationship among Viagra, Club Drugs and HIV sexual risk behavior in drug using men with a sample diverse in sexual orientation and demographic scope. Participants were 640 males recruited from three HIV prevention programs in Los Angeles County. Mean age was 43.97 years, ranging from 18.7 to 70.3 with almost 25% over 50. Sexual orientation was 79% heterosexual, 8% bisexual and 12% gay. Racial composition was 45% white, 35% black and 19% Hispanic. NIDA's Risk Behavior Assessment and a Club Drug/Viagra addendum were used to collect socio-demographic, substance use and sexual risk data. Multiple logistic regression models were constructed along with chi-square tests of association and some t-tests. White race was a major risk factor. No age effect was found. MSM were more likely to use Viagra. Insertive anal sex was a significant co-factor among heterosexual Viagra users involved in transactional sex with women. In the overall sample and the subsets of heterosexual, MSM, younger and older men, predictive models all identified club or designer drugs as significant co-factors in the use of Viagra. Different patterns of drug co-factors were observed for each subset. We detected consistent positive associations between the use of Viagra and the use of amphetamines immediately before or during sex. Viagra use has moved into a new generational context and now complicates the sexual risk and intervention equations for all men, particularly MSM as well as more hidden subgroups.