Research links negative parenting and parental psychopathology to poorer outcomes among youth. Less research examines these effects simultaneously during late adolescence. The current study examines parenting, parental psychopathology, and late adolescent psychopathology as reported by late adolescents (N = 328) with the use of structural equation modeling. Results of measurement models indicate that parental psychopathology and parenting are related to late adolescent psychopathology. However, results of structural models indicate that the effect of parenting on late adolescent psychopathology becomes non-significant in the paternal model and reverses in the maternal model. Interestingly, maternal parenting is associated with higher levels of late adolescent psychopathology, suggesting that mothers provide their late adolescents with more supportive parenting when it is needed most. Overall, results suggest the importance of examining parenting characteristics simultaneously in the context of gender and other variables.