Hellyer's career spanned the years 1947–2012 and included local and national network radio programs as a disc jockey, radio and television news reporter and anchor, sports reporter, game show television host, and live and recorded television and radio commercials.
Chuck Schaden, Chicago radio history buff and host of 'Golden Age of Radio' programs on WBBM-AM and WNIB 97.1 FM wrote that "Art Hellyer was the king of Chicago radio", and Hellyer "became the originator and perhaps the foremost exponent of zany, off-the-wall comedy on the air." During his career Hellyer's shows achieved #1 in ratings (numbers of listeners) on three different Chicago radio stations during his program time slots.
Hellyer succeeded with innovative on-air antics and creativity that were not typical yet on radio in the 1950s including wisecracks, offbeat and topical humor, ad-libbed interplay with recorded sound bites including comedy album soundtracks thrown at him by his studio engineer, playing up to four recorded commercials simultaneously to reduce commercial time, playing Christmas music in July, humorously faking live interviews and commercial products, reporting time one hour off or the wrong music performers on April Fools' Days, betting a competitor deejay on another radio station he could play the same songs simultaneously which he won by actually streaming on air the competitor's broadcast live on his station, and taking creative liberties with commercial announcements that sometimes led to friction with management.
Hellyer's professional broadcasting career began early in 1947 at WKNA-AM, Charleston, West Virginia and included hosting radio programs at WOWO-AM Fort Wayne, Indiana; WMRO-AM Aurora, Illinois; and WISN-AM, WMAW-AM and WMIL-AM, Milwaukee, Wisconsin.
Hellyer's break into a major market was in May 1950, when his daily postcards mailed to WCFL-AM Chicago's program director asking to "rescue" him from Milwaukee resulted in an unorthodox on-air live audition for 50,000 watt WCFL while broadcasting his show on air on WMIL-AM in Milwaukee. WCFL hired Hellyer, and by 1952 Hellyer was given the drive-time 6am – 10am radio slot where he was promoted as the "Morning Madcap."
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