American Media had no interest in Cracked, there were after some other titles. The plan was to shut down the humor magazine. But an editor at WWN asked them to keep it going and be the editor. They agreed to this, so the late Dick Kulpa, oversaw the death spiral of Cracked. The parent company slashed the budget so payments were reduced (if not eliminated, in some cases). Then they had distribution problems getting the issues out. The publication schedule grew erratic. Dick did what he could do to keep it afloat.
During one of the longer gaps between issues, Kulpa approached several of the Cracked regular contributors and offered us the opportunity to write for the Weekly World News, as a way to keep us...paid. I was reluctant, I really didn't know if it was something I could do. There were rules to creating stories for WWN and the idea of trying to drag out a joke that was basically a headline into a 300-500 word article was daunting.
Then he tossed me another idea; would I want to be their advice columnist, Dear Dottie? Weirdly, this seemed more like something I could pull off. I would write a few letters, then write the answers and submit it. I gave it a shot and they printed the column. This was insane, but the money was okay and the checks cleared (which was becoming an issue with Cracked).