This article describes the life circumstances and risk behaviors of 552 adolescent males returning home from jail. Most young men reported several sources of support in their lives and many had more tolerant views toward women and intimate relationships than portrayed in mainstream media. They also reported high levels of marijuana and alcohol use, risky sexual behavior, and prior arrests. Investigators designed the Returning Educated African American and Latino Men to Enriched Neighborhoods (REAL MEN) program, a jail and community program to reduce drug use, HIV risk, and rearrest. By helping participants examine alternative paths to manhood and consider racial/ethnic pride as a source of strength, REAL MEN addressed the assets of these young men as well as their challenges. Our findings suggest that interventions that emphasize the assets of these young men may be better able to engage them than programs that seek to impose adult values.