His first show was on WKNA in Charleston, WV in 1947 interviewing auto salesmen. Despite behaving like Art Hellyer, he was not fired from that job. (In his book he actually devotes a whole chapter to what he was not fired for.) It was a theme in his career. His zany behavior got him ratings. WBBM famously fired him over a dress-code violation and then re-hired him. As he told the Chicago Tribune in 1996 more simply that he got fired "a lot."
"...I counted 14 times. It may have been more than that... I always said every one of my battles was over creative control. I wanted to be creative, and they wanted control."
It's hard to say which of his programs was the most important to his career as several of them held the number one slot in one decade or another. In the 1950s his program The Art Hellyer Show aka the Morning Madcap on 1000 WCFL-AM, again on 780 WBBM with his Supper Club shows in the '60s while also doing mornings at WAIT, Then again on WLS-FM in the '70s until they went progressive rock in 1969. He was number one again on 1160 WJJD-AM in the '80s. His time at WOPA straddles some of that doing WOPA Art Hellyer's Memory Lane in the mid sixties.
What probably got his career going the most was his time on on WCFL. There he was given carte blanche for the first time in his career and he more or less ran amok. He offended big sponsors, like Coca-Cola and General Motors but the listeners loved it. In he did spend a few serious on air. He advocated for the seat belts in cars in the 1950s and in 1960 spent time explaining to listeners the importance of the then brand new Polio vaccine to quiet the anti-vaccination nuttters. In 2011 he made another come back of sorts and began Internet radio station Party 934. Not bad for a guy that one quipped that "...the average life of a disc jockey in Chicago is three years."