The focus of this paper is on HIV sexual risk taking among a community-based sample of disadvantaged African American adults. The objective is to examine multiple factors associated with sexual HIV risk behaviors within a syndemic conceptual framework. Face-to-face, computer-assisted, structured interviews were conducted with 1535 individuals in Atlanta, Georgia. Bivariate analyses indicated a high level of relationships among the HIV sexual risks and other factors. Results from multivariate models indicated that gender, sexual orientation, relationship status, self-esteem, condom use self-efficacy, sex while the respondent was high, and sex while the partner was high were significant predictors of condomless sex. Additionally, a multivariate additive model of risk behaviors indicated that the number of health risks significantly increased the risk of condomless sex. This intersection of HIV sexual risk behaviors and their associations with various other behavioral, socio-demographic, and psychological functioning factors help explain HIV risk-taking among this sample of African American adults and highlights the need for research and practice that accounts for multiple health behaviors and problems.