This cross-sectional study of 540 homeless ex-offenders exiting prisons and jails assessed sociodemographic, childhood, and drug-related differences. Older ex-offenders from prison were more likely to have been married, come from a two-parent family, and used crack, whereas younger ex-offenders from prison were more likely to have used methamphetamine. Older ex-offenders from jail were more likely to be African American, have children, and report a history of crack and injection drug use, whereas younger ex-offenders from jail were more likely to have engaged in binge drinking and be in a gang. Our findings showcase the need to understand unique correlates of younger and older incarcerated populations.