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Problematic pornography viewing is receiving increased attention as a men’s issue. However, few studies have examined how culturally constructed masculine role norms relate to pornography problems and how individual differences may moderate these associations. Men (N = 520) were recruited online to participate in a survey examining how conformity to masculine role norms was associated with problematic pornography viewing dimensions and how self-esteem moderates these associations. Controlling for pornography viewing frequency, religious identity, and sexual orientation, structural equation modeling revealed power over women and playboy norms as associated with increased problematic pornography viewing, whereas emotional control and winning norms were negatively related to problematic pornography viewing. Of these associations, power over women norms produced consistent positive direct effects across all dimensions, whereas emotional control norms produced consistent negative direct effects. Latent variable interactions reversed the negative direct effects, suggesting men low in self-esteem but high in emotional control and self-reliance norms demonstrate increases in problematic pornography viewing. Interactions similarly evidenced positive relationships between conformity to playboy norms and problematic pornography viewing, with an exacerbation effect for those low in self-esteem. Findings suggest that men’s pornography viewing may be tied to their expressions of traditional masculinity. In addition, men with low self-esteem may be especially drawn to pornography, potentially as a way of overconforming to and performing certain male role norms. Implications for practice include exploring masculinity ideology with male clients struggling with pornography viewing problems and integrating masculinity as an important cultural consideration within established treatment modalities for pornography addiction.