Although existing studies have found that problematic parental behaviors affect children's later life course outcomes, few have focused on the gender and urban-rural differences in the effects of these behaviors on school-to-work transition. This study traces the school-to-work trajectories of Chinese people born between 1930 and 1979 to investigate the effects of their parents' problematic behaviors on school-to-work transition and the gender and urban-rural differences in these effects. We found that individuals whose parents drank heavily and committed crimes completed the school-to-work transition earlier and were more likely to engage in agricultural labor, enter the labor market with low education levels, and experience unemployment after leaving school. The effects of parental alcoholism and gambling on school-to-work transition varied according to urban-rural residential status. Youths with urban hukou (household registration) whose parents drank heavily were less likely to have stable jobs. Further, women and youths with agricultural hukou whose parents gambled and committed crimes had a higher likelihood of being disadvantaged in the transition from school to work and of facing multiple risks, including hazards of agricultural work, precarious work, and unemployment.