Born in Towson, Maryland, Phelps grew up in nearby Baltimore City. He has at least one sibling, an older sister. He attended Calvert Hall College High School in Towson. As a youngster he listened to Casey Kasem and his American Top 40 countdown show and became very knowledgable about what the current hits were. After winning a station contest he received a tour of the studios of Baltimore’s WBSB (B-104); at age 15 he then knew that being a radio personality is what he wanted for a career. The deejays that influenced Phelps included Baltimore’s Johnny Walker on WFBR (AM), with his sound effects and personality-driven style, as well as some of the jocks on B-104. In addition, he listened to Rick Dees and the nationally syndicated Rick Dees Weekly Top 40 countdown show, which included plenty of sound effects and humor. A final influence was the fast-talking Terry “Motormouth” Young, whom he heard on WCAU (98.1) in nearby Philadelphia during its early-mid-1980s Hot Hits phase.