Results suggest that involvement in structured discretionary time (DT) activities was not associated with lower levels of either delinquency or depressive symptoms. However, the types of DT activities (active unstructured, and passive unstructured) were associated with adjustment, but these relationships varied according to the neighborhood environment in which the adolescent resides. Adolescents who spent more discretionary time engaged in passive unstructured (PU) activities exhibited higher levels of depressive symptoms only if they resided in less dangerous neighborhoods; spending a lot of time watching television and idling was associated with more depressive symptoms only for adolescents who lived in more cohesive and safe neighborhoods. Given the cross-sectional nature of these findings, however, it is not possible to determine if urban African-American youth who live in less dangerous neighborhoods exhibit more depressive symptoms and then choose to get involved in more passive unstructured activities, or if being more involved in such activities leads to more depressive symptoms; involvement in passive activities may be either a precursor to or an indicator of elevated depressive symptoms. Data were collected for 246 young African-American adolescents recruited from 8 public K-8 schools in different urban areas of Chicago. Tables, figures, and references