This thesis seeks to utilize a distant reading of seventeen essays written by James Baldwin alongside sustained close readings of three topics within those essays in order to understand why Baldwin has maintained increased popularity when the original historical context of the essays resulted in fame and critical acclaim, but not major literary awards. The author ran these seventeen essays through topic modeling software, and then engaged with critical and scholarly close readings to establish qualitative and quantitative explanations of patterns that exist in Baldwin’s work. By connecting the findings of work under both the digital humanities as well as African American literary studies, the nature of Baldwin’s essays that ascribes their popularity can clearly be understood.