Every generation has icons attractive to adolescents and equally repugnant to adults. This article examines antihero characteristics, their appeal to adolescents, and how adults can respond to adolescents enamored of antiheroes. The stage personas of antiheroes champion rejection of the mainstream, assail adult constraints and expectations, explore frightening topics, and ultimately fulfill the adolescent fantasy of surviving alienation and emerging victorious over parents and peers. But antihero idolization also tests the adult's defenses. Adults, fearing loss of control and rejection by the adolescent, sometimes resort to primitive defenses mismatched to the developmental needs of the adolescent. Adults, as much as the adolescents, benefit from examining their individual reactions to the antihero and how their current relationship can accommodate this intrusion. The antihero phenomenon presents adults with an opportunity to model ways to think through that which is uncomfortable and to navigate together the adolescent's developmentally normative separation efforts.