This chapter explores transcultural perspectives on popular music aesthetics and gender in Norway through case studies of male celebrities born around 1980: the duo Madcon, Jarle Bernthoft, Lars Vaular, and Sondre Lerche. The analysis focuses on the practices of self-fashioning a persona in the realm of the popular, involving the aesthetics of masquerade, the ordinary, and escapism. Conceptually, the chapter draws from Bakhtin, Eyerman, Frith, and other influential voices in the literature on cultural performance and identity. The discussion also sheds light on fundamental issues in popular music aesthetics, demonstrating how the musicology of popular music can offer a unique cultural critique of identities that may appear to be “only entertainment” but in fact mediate powerful ideologies.