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Although a role for family and parent factors in the development of behavioral problems in childhood is often acknowledged, the roles of specific parental characteristics in relation to specific child actions need further elucidation. We studied parental "Big Five" personality traits and psychiatric diagnoses in relation to their children's antisocial diagnoses and naturalistically observed antisocial behaviors, in boys with and without the diagnosis of Attention-Deficit Hyperactivity Disorder (ADHD). First, regardless of comorbid antisocial diagnosis, boys with ADHD, more often than comparison boys, had mothers with a major depressive episode and/or marked anxiety symptoms in the past year, and fathers with a childhood history of ADHD. Second, compared to the nondiagnosed group, boys with comorbid ADHD + Oppositional Defiant or Conduct Disorder (ODD/CD) had fathers with lower Agreeableness, higher Neuroticism, and more likelihood of having Generalized Anxiety Disorder. Third, regarding linkages between parental characteristics and child externalizing behaviors, higher rates of child overt antisocial behaviors observed in a naturalistic summer program were associated primarily with maternal characteristics, including higher Neuroticism, lower Conscientiousness, presence of Major Depression, and absence of Generalized Anxiety Disorder. The association of maternal Neuroticism with child aggression was larger in the ADHD than in the comparison group. In contrast, higher rates of observed child covert antisocial behaviors were associated solely with paternal characteristics, including history of substance abuse and higher Openness. Results provide external validation in parent data for a distinction between overt and covert antisocial behaviors and support inclusion of parent personality traits in family studies. The interaction of maternal Neuroticism and child ADHD in predicting child aggression is interpreted in regard to a conceptualization of child by parent "fit."