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Without spoiling too much, in Radio Milwaukee’s new podcast Backspin, the search for Milwaukee’s first rap song yields an incredible story but a disappointing answer. The city’s first rap song, it turns out, was anything but a labor of love, and it would be years before the city produced a second one. Much of the history of Milwaukee rap reads like this. For most of its run, the city’s rap scene has been defined by false starts, dead ends and dry spells.
The search for the city’s first rap song made us start thinking about other milestone tracks in Milwaukee rap. And so, ahead of this month’s Hip-Hop Week MKE, we’ve compiled this list of the most important tracks in the history of the local rap scene. Instead of ranking them, we’re presenting them chronologically, and as a result they tell a story. These 10 songs chart Milwaukee rap’s slow rise from a niche scene struggling to get off the ground to the booming source of local pride it finally became.
A few caveats before…