ABSTRACT Three primary purposes guided the present study: to examine the role of adolescents’ favorite television character characteristics on adolescents’ wishful identification toward the characters’ job, to examine the role of television and family on adolescents’ vocational anticipatory socialization, and to explore whether the associations varied by gender. Data were collected from 330 adolescents. Intrinsic work values, easy-going work perceptions (as reported by the adolescents), and gender of adolescent girls’ favorite television characters were positively associated with wishful identification. The television characters’ easy-going work perceptions were positively associated with adolescent boys’ and girls’ own easy-going work aspirations. Finally, communication with parents about work moderated the association between parents’ and adolescent boys’ and girls’ easy-going work aspirations.