For decades authenticity has been of great interest in media and communication research. With this study, we aim to contribute to the research with a new perspective where authenticity is examined in artists who use influencer marketing on social media. With two qualitative focus group interviews, we examine how two previously separate professional roles, influencer and artist, now merge in their interests and strategies to influence their audience via social media platforms. By analyzing and interpreting young Swedish women’s experiences of artists’ advertising collaborations, we seek to understand the concept of authenticity's influence, power and meaning in the digital era. This is done using the three theories: influencer marketing, social capital and branding. The results confirm the dynamic role of the concept of authenticity in society and that whether something or someone is authentic is situational. The concept of authenticity is perceived as important in some contexts and less important in others. There is a clear tolerance for inauthentic behavior within the artist community. However, there is also a perceived limit to how much advertising through influencer marketing an artist can do before it has a negative impact on the artist’s perceived authenticity. The most significant factor is the artist's choice of brand to collaborate with. Our conclusions also show that there is an awareness of the intertwining of the two professional roles and a feeling that most artists and influencers are in a “gray area” where the boundaries between the roles are blurred. This means that new relationships and patterns of cooperation between artists and companies are created, and the dynamics of both the entertainment and advertising industry is changing.