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This essay uses Big K.R.I.T.’s (Justin Scott) career to examine the contributions and unique challenges of contemporary Mississippi and Alabama Hip-Hop artists. Mississippi and Alabama have direct connections to the origins of Black American music like Blues, Jazz, Rock & Roll, and Gospel, which lay the foundation for Hip-Hop. Despite this enduring legacy, Hip-Hop artists from the Deep South experience additional obstacles in the entertainment industry- specifically contemporary Hip-Hop. In Big K.R.I.T.’s theory “Geography Lottery,” he suggests that performing artists in media centers like Los Angeles or New York City enjoy the success and ease of mainstream entry. In contrast, artists from Southern or rural places find it more difficult to obtain similar access. This essay utilizes lyrical and textual analysis of interview statements, song lyrics, and production choices to assess these artists’ barriers. The research demonstrates their persistence in uplifting and defending their home states and the South from close-minded statements and negative assumptions in media appearances and music performances. This essay bolsters Scott’s demand for recognition of Mississippi and Alabama in the legacy of Hip-Hop.