Masks are essential as narrative and symbolic manifestations in some comedies, perhaps most notably Chuck Russel’s The Mask (1994), starring Jim Carrey as Stanley Ipkiss. The chapter focuses on this specific film and the meaning of masks in this context. Moreover, it briefly highlights other comedies or hybrid genres of relevance. Theoretically, it hinges on both persona and personality types in popular culture such as the dark anti-hero and stereotypes such as the agreeable “Nice guy” (Boman, The applicability of big five facets and dark tetrad traits on Yukio Mishima’s novel protagonists. East Asian Journal of Popular Culture, 7(1), 95–113, 2021; Boman, The gray nine and parallel personality patterns: Big five, dark tetrad, and a “well-rounded” personality profile. Integrative and Psychological Science, 58(4):1300–1316, 2024; Jonason et al., The antihero in popular culture: Life history theory and the dark triad personality traits. Review of General Psychology, 16(2), 192–199, 2012).