Authenticity within the hip-hop community has been a topic of conversation amongst researchers for a number of years. The hip-hop movement started in the 1970’s and has steadily grown over the years into a worldwide phenomenon. Although the success of hip-hop is regarded by the majority of the hip-hop community as positive, it has also caused significant issues in terms of (mis)representation and (in)authenticity. One aspect of authenticity that has been foregrounded is race. Can a white hip-hop artist be considered authentic in the hip-hop discourse community? To examine this question, this paper will explore the authenticity of white hip-hop artists Macklemore and Iggy Azalea. In order to explore how their authenticity has been both constructed and challenged by the hip-hop discourse community, authenticity will be considered in two, overlapping forms: authenticity in terms of the linguistic community and authenticity in terms of the hip-hop community. Through an examination of the artists’ lyrics, commentary in response to their music videos, and interviews with the artists, I will analyze how Macklemore and Azalea have attempted to construct themselves as authentic hip-hop artists and how others have contested their identity. Through this analysis, I will investigate how authenticity has evolved to include or exclude community members, specifically how authenticity is ascribed or contested when a community member’s most visible identity feature (in this case race) does not align with the norms.