An art school dropout, Derf worked on a garbage truck before deciding to give cartooning a try. He attended Ohio State University, where he drew political cartoons for the school paper for three years and caused such controversy school officials put a 1-year limit on all future cartoonists. After graduation, he landed a similar position on a paper in Florida but was fired after two years for, as the editor put it, "general tastelessness." He moved to Cleveland and The City debuted in the now-defunct Cleveland Edition in 1990. A year later, he began selling it to other alternative papers.