He listened to a lot of radio while confined to bed for rheumatic fever for a year, and started broadcasting at the age of 14 in his hometown of Chicago at an educational station, WBEZ. He moved to Chicago's WCFL as a summer replacement and remained there eight months.
Harry next became program director at WPEO in Peoria, Illinois, and hosted their morning show. WPEO became the top-rated station in six months, and Harry, well known in the Midwest, was recruited by New York City's WMCA.
In 1959 Harry joined WMCA as a morning personality with great success for about eight years. WABC hired him in 1968 to replace Herb Oscar Anderson as their morning drive air personallity. He stayed at WABC until it hit troubled times in 1979. In 1980 he became the morning personality at Oldies station WCBS-FM. He retired in 2003.