Milwaukee hip-hop is in a great place. After Arrested Development, Coo Coo Cal, and Baby Drew helped put local rap on the map between the early ’90s and the turn of the century, the genre began to struggle for an identity and recognition outside city limits. About five years ago, something special started to take shape. Months after IshDARR’s Broken Hearts & Bankrolls continued the young emcee’s ascent, days before WebsterX’s Daymares release show, and with countless other local rappers putting out remarkable releases along the way, we figured it was prime time to reexamine the state of Milwaukee hip-hop.

Host Tyler Maas recently met with up-and-coming musician Vincent VanGreat at the Cactus Club. They were also joined by Promise, a V100.7 radio personality who highlights the best in Milwaukee-made hip-hop every weekend on his “Heat From The Street” segment. Together, the trio talked up the history of Milwaukee hip-hop, its ups and downs, struggles rappers face in this market, and who is helping to bolster the city’s rap rep.

This episode is brought to you by Surly Brewing and Pridefest. Music in this episode comes courtesy of Piles (“Blue Glue”) and Vincent VanGreat (“To The Stars”). Subscribe to On The Record via iTunes or Stitcher (for free!).