Chuck Chillout (along with DJ Red Alert) was brought to KISS FM in New York as an answer to WBLS' Mr. Magic and Marley Marl. Chuck debuted in October 1983 from nine to midnight on Fridays as part of KISS' Mastermix series. It wasn't long before his show was essential listening for hip-hop fans.
The show continued on KISS until the late 80s when Chuck was invited to WBLS for an interview by his idol Frankie Crocker. Chuck was put on suspension for appearing on a competing station and he used the opportunity to jump ship. He remained at WBLS for a couple of years before becoming a VJ for Video Music Box