Inner-city male adolescents in jail in New York City (N = 427) were interviewed to examine correlates of cocaine or crack use. Twenty-three percent had used cocaine or crack in the month before arrest and 32% reported lifetime use. Substantial rates of robbery, murder, other violent crime, weapons possession, and drug dealing were found. However, type of crime, including violent crime, was not related either to cocaine/crack use or to drug dealing. Current cocaine/crack users were more likely to use alcohol, marijuana, and intranasal heroin; to have multiple previous arrests; to be out of school; to be psychologically distressed; to have been sexually molested as a child; to have substance abusing parents; and to have cocaine/crack-using friends. They were also more likely to have frequent sex with girls, to be gay or bisexual, and to engage in anal intercourse. The findings should be considered in developing more effective drug abuse prevention and treatment interventions, and HIV prevention education, for incarcerated at-risk adolescents.