The son of rap music legend Joseph “Run” Simmons, Diggy (born Daniel Simmons III) found fame via his family’s reality TV show, Run’s House. Although he grappled on the show with issues like his family’s affluence and influence, Diggy has chosen to follow in his father’s footsteps as a rap artist and entrepreneur. Along with releasing two mixtapes, “The First Flight” and “Airborne,” he’s appeared on “Like ’Em All,” the debut single of young R&B sensation Jacob Latimore. The 16-year-old Diggy also launched his own sneaker brand, Chivalrous Culture. In 2012, Diggy released his major label debut, Unexpected Arrival.