In 2010, James Franco debuted his exhibition “The Dangerous Book Four Boys” at the Clocktower Gallery. He appropriated his title from the Igguldens’ guidebook The Dangerous Book for Boys (2006). This paper explores Franco’s representation of boyhood, focusing on his anxiety over traditional gender roles. Dangerous depicts boyhood as a homosocial and homoerotic realm in which women are both envied and elided. Franco’s vision of boyhood is premised upon a longing for both domestic structures and practices. The exhibit is organized around several small rough-hewn wooden structures resembling small houses. Inside the constructions, the films Destroy House and Castle depict young men destroying identical domiciles with axes, shotguns and blowtorches. Ironically, these violent depictions are safely contained within intact replicas of the very structures being destroyed in the films. These constructions are emblematic of Franco’s fraught relationship to masculinity, stereotypical gender roles and domesticity.