Much is known about contemporaneous correlates of homelessness from studies of homeless individuals. However, few studies have prospectively examined early antecedents and prevalence of homelessness in community populations. We use data from a 35-year study of a community population of African Americans to examine relationships between homelessness and prior structural, family, school, and behavioral influences. Nearly 22% of males and 16% of females reported homelessness between ages 15 and 42, providing a rare estimate within an African American urban community population. In bivariate analyses, lower school bonds, depressed mood, violent behavior, and running away in adolescence are predictive for both males and females. Teen parenting and angry mood are unique influences for females, while for males, poor first grade classroom conduct and adolescent substance use are unique risks. In multivariate analyses, poor classroom conduct and weaker school bonds predict homelessness among males, while teen parenting does so for females. Running away before age 15 is strongly predictive of later homelessness for both males and females. These results reveal the relative influence of multiple, interrelated early risks on homelessness and confirm our hypothesis that factors linked to other poor outcomes also relate to homelessness, underscoring another benefit to early prevention efforts.