Personal branding within the music industry has long fallen under the supervision of profit-centric major record labels, whose control extended throughout artist’s music, copyrights, merchandising, and fair-use compensation. This paper explores how artists’ branding has evolved within the recording industry alongside the development of emerging technologies and the discovery of certain patterns in consumer behavior. Starting with an overarching exploration of the origins of commercialized music, this paper iterates how certain record labels ascended the corporate hierarchy to influence consumers’ accessible listening options. This understanding leads to an analysis of the inception of illegal file-sharing websites as an outlet for music distribution, as well as its long-lasting effects on industry distribution tactics and music streaming platforms. This paper then narrows to the origins of the rap industry, delving into the traditionally-rooted experiential celebrations that birthed such an impactful genre. Following an understanding of the history of the recording and rap industries, this paper identifies the modern music listener’s behaviors and choices, supplemented by an examination of how consumer social technologies have motivated these changes. To best understand the role of these evolving perceptions, this paper evaluates four successful rap artists - Chance the Rapper, Tekashi 6ix9ine, Lil Nas X, and Travis Scott - and determines the strategies employed by these individuals and their branding teams. Finally, in determining these strategies, this paper outlines the essential takeaways from this research that would aid in the advancement of an artist’s personal branding today.