This study aims to investigate the effects of a history of unemployment, conviction and incarceration on the likelihood of being employed in a sample of disadvantaged youths. All youths (N = 540) were institutionalized in adolescence. From age 18 to 32 official data were available on employment, convictions and incarceration. To control for unobserved heterogeneity, fixed effects models are used to estimate effects of unemployment, conviction and incarceration on the likelihood of employment. Results show that for men, a criminal background does not damage employment prospects when a history of unemployment is taken into account. However, for women, a criminal record does lower employment chances in addition to the detrimental effects of unemployment.