Alongside New York City, Los Angeles, and Atlanta, Minneapolis, Minnesota has become a cradle of hip-hop, breeding a distinct style that has grown swiftly from the 1980s to the present day. While Minneapolis is more commonly associated with the upbeat funk rhythms and prominent synthesizers of its favorite son, Prince (1958 – 2016), Minnesota hip-hop provides a strikingly contrasting listening experience characterized by dark, self-deprecating, and introspective traits. Minnesota and other regional hip-hop scenes have been overshadowed by academic studies that focus principally on New York City or Los Angeles. In this thesis, I advocate for a shift away from the Billboard charts and the East and West Coast, into the world of underground hip-hop of the Upper Midwest. This thesis explores and documents the development of hip-hop in Minnesota, specifically the Twin Cities and independent label Rhymesayers Entertainment, who have established Minneapolis as one of the largest hip-hop hubs in the country. A location that thrives on the “Minneapolis sound” of artists such as Prince and Morris Day (b. 1956), Minnesota hip-hop offered an alternative and more calloused genre for artistic expression. Following the arrival of hip-hop in Minnesota in the early 1980s, a group of like-minded youths gathered together to practice the art of hip-hop, which led to the creation of the Headshots Crew. Despite not having much of a local scene, the Headshots Crew created opportunities and performance spaces to showcase their talents, which eventually led to the creation of their own label, Rhymesayers Entertainment. Unlike many other independent labels Rhymesayers has found a way to sustain their success for over 25 years while maintaining their independence. Their most famous artist act is rap duo Atmosphere. By incorporating primarily biographical and historical methodologies this study means to create a cohesive understanding and foundation of Minnesota hip-hop.