Why do pop stars employ gender stereotypes to come across as credible? And how can we evaluate the paradoxes of these stereotypes in the artist’s persona? To begin with, I want to consider that the notion of honesty and truthfulness is not the responsibility of the artist alone, but part of a broader ideological context of popular music. As Nicola Dibben observes: “Belief in a singer’s authenticity reflects one of the prevalent ideologies of music creation and reception and of the person in contemporary society – the idea that people have an inner, private core” (Dibben 2009, 317). During the course of this chapter, I turn to the connections between this “private core”, stereotypes of gender, and the use of the figure of the child in the audiovisual construction of the pop persona. My aim is to contribute to the ongoing debates on authenticity in popular music studies by examining specific gender norms and their empowerment of the pop artist.