In the 1980s, Def Jam and Run DMC brought together the world of rap to the mainstream. For those not old enough to remember rap group Run DMC, the reality show Run's House introduced us to the Simmons family. Vanessa, Angela, Jo-Jo, Diggy, Russell, and Miley
Born the son of Rev Run and the nephew of rap mogul and Def Jam co-founder Russell Simmons, Diggy Simmons grew up on this show and emerged as the best rapper among his siblings. He would later get into acting as well, becoming a cast member on the Kenya Barris hit show Mixed-ISH. His role as Doug turned into a real-life, although short-lived romance with co-star Chloe Baily.