[6] Members of Kent's radio audience usually felt as if they knew him personally, even though they might never have met him — a familiarity facilitated by "his lively exchange with guests and co-workers during his broadcasts".
[7] Kent began working in radio in 1944 when he was 16 years old and still in high school,[6] hosting a classical music program on WBEZ in Chicago.
[9] By the late 1940s, he was working at two stations—acting in old-time radio dramas on WMAQ in Chicago and hosting a record program on WGRY in Gary, Indiana.
[12] In March 1963, Kent headed the disc jockey lineup at WVON, a newly launched Chicago station that resulted from the purchase of WHFC and a change in format to "uncompromising soul-style rhythm and blues.
Robert Pruter, in his book, Chicago Soul, noted that Kent had a distinct on-air style: "Unlike many other deejays of the day, black or white, he never shouted or screamed or used an artificial patter.
[14] Gary Deeb, radio-TV critic for the Chicago Tribune, noted that Kent's popularity as a night-time disc jockey attracted an audience of young people who also listened to the station at other times.
[18] In the mid-1960s, Kent owned the Times Square Club, a rhythm-and-blues venue that leased space in the Packinghouse Workers' Hall on South Wabash in Chicago.