Cunningham has been on 50,000-watt radio station 700 WLW for over 30 years, beginning in 1983. His first regular show on the station was at night, generally from 9:00 p.m. until midnight. His show was not heard during the summer months, when WLW broadcasts Cincinnati Reds baseball games. In the late 1990s, Cunningham’s show was moved to early afternoons, which put his show directly opposite that of one of his favorite radio presenters, Rush Limbaugh, whose show is heard on sister station WKRC.
Cunningham’s WLW show went on a brief hiatus in June 2010 due to a contract dispute. Soon after, WLW’s owner, Clear Channel, announced that he signed a long-term agreement to stay with the station. In released remarks commenting on his decision, Cunningham said, “Cincinnati is my home. The first air I breathed. The first milk I drank was from Cincinnati.