This mixed-methods study identified correlates of unemployment among homeless young adults in five cities. Two hundred thirty-eight homeless young people from Los Angeles (n = 50), Austin (n = 50), Denver (n = 50), New Orleans (n = 50), and St. Louis (n = 38) were recruited using comparable sampling strategies. Multivariate logistic regression results indicate that homeless young adults were more likely to be unemployed if they had been on the streets longer, currently lived on the streets, earned an income from panhandling, and were addicted to drugs. Quantitative findings are expanded on with focus-group data from a group of homeless young people in Los Angeles regarding their challenges in locating and maintaining employment. Employment-related barriers for this population include prior homelessness, geographic transience, previous felonies, mental illness, and addiction. Findings suggest that homeless young adults' employment status and use of specific income-generating activities may be influenced by demographic, environmental, and geographic contexts. (Contains 3 tables.)