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Beauty messaging is changing, with corporations and widely followed social media influencers expanding their reach into the world of men’s appearance practices. Together, these corporations and viral stars enjoin men to modify and perfect their faces and bodies through rigorous workout regimes, style advice, and intensive cosmetic interventions. Sometimes called, body work, these practices require consistent maintenance and costly effort. While the literature on body work has paid significant (and important) attention to practices of beautification as they exist among women, less is known about how men engage with body work and beautification. We know similarly little about whether men’s engagement with beauty and body work—traditionally feminine domains—signal any real shift in existing distributions of masculine power and hegemonic privilege. In what follows, we draw from the literature on beauty, and from what is known about masculinity and its contemporary presentation on social media platforms to comment on the ways in which men beautify and, the boundaries they draw around their body work. We use the viral moniker “looksmaxxing” as a productive case study to investigate body and boundary work among men online. Specifically, we draw from a collection of 60 social media videos and from a sub-sample of their attendant comments to trace men’s engagement with body work and their response to beautification. We find that men’s engagement with beauty and body work is often accompanied by allusions toward traditional notions of gender and sexuality, or else, couched within broader appeals toward hegemonic masculinity. Publicly available comments, meanwhile, point to the various pressures, privileges, and penalties men’s engagement with beauty and body work entail.