Data were obtained from 162 high school dropouts through interviews and questionnaires containing demographic, labor market, social-psychological, and deviance measures. Labor market experience variables included employment status, total months unemployed since leaving school. In total, 31 percent of the high school dropouts reported having been questioned by the police and 23 percent said they had been convicted in court of a nontraffic crime in the past year. Multiple regression analysis demonstrated a relation between labor market experiences and crime, but such analysis also highlighted the importance of distinguishing among labor market variables. Unemployment, particularly for males, was related to most measures of crime and drug use. Similarly, an unstable work history was related to several dependent variables, and this relation persisted after controlling for other labor market and economic variables as well as for family status and length of time since dropping out of school. No labor market variable, however, was related to violent crime. Further, financial status appeared unrelated to crime measures, and total amount of time unemployed was related only to alcohol use. The absence of a link between financial status and property crime casts doubt on both 'economic hardship' and 'strain' explanations of property crime, at least for high school dropouts. The combination of being male and unemployment is particularly related to being stopped and questioned by the police, to more frequent drug use, and to more involvement in crime. 2 tables, 26 references.