He is known as the original host on 106 & Park, which originally aired on BET.
After co-hosting the show for five years with Free (Marie Wright), Calloway left the show on July 28, 2005.Calloway then moved to being a correspondent and occasional anchor on the entertainment news program Extra from 2005 until July 2019, when the show's producer Telepictures terminated him, due to a number of sexual assault allegations.He is an alumnus of Saint Benedict's Prep in Newark, New Jersey and Howard University in Washington, D.C..