DescriptionThis thesis chronicles Masekela's transition from African refugee to Grammy nominated artist while also encompassing a musical analysis of his work before and including The Promise of the Future. This thesis will provide brief biographical information of Masekela’s life as well as a sociological analysis to give context to his place in US pop culture. This study discusses Masekela’s upbringing in South Africa and explores his transition into 1960s America. This thesis argues that Masekela faced an authenticity complex when breaking into the US market because he defied the expectations of what US audiences thought Africans to be. Masekela overcame this obstacle with the release of The Americanization of Ooga Booga (1966). A musical analysis and critique of the first three albums with an emphasis on Masekela’s breakthrough compositions will be part of this thesis. This thesis concludes with a brief analysis of the cultural and racial impact of Masekela’s work both in the United States and South Africa.