I had been submitting stuff on and off to Mad magazine for years. They actually ran an ad in the NY Times (a newspaper of some note in analogue times) looking for new writers to submit material. So I did and they bought the first thing I submitted! But then, nothing. I knew Cracked existed, the Pepsi to Mad's Coke, but didn't know much about it. Until finally I got a copy and decided to set some of the things I had submitted to Mad to them. And they were WAY more receptive. I remember getting a call from the editor, Andy Simmons, telling me how much he liked my stuff. Let me know that a piece was going in shortly and asked me to send more. I was both over the moon and Mad.
I got a check and 2 free copies of the magazine. I was a grown man, but I was so excited and thrilled to have someone take note of my writing. I sent them everything, old Mad material, adapted skits, epic gags. I attempted to do something the magazine hadn't done in ages, creating running gags. When they ran Upside/Downside, I quickly began work on others. It was a slick format to sell jokes in, be they topical, seasonal or perennial. There would be other attempts as well, but I never quite got the bits "mainstreamed" into the canon of the magazine.
#322, Dec. '97
Here's the first piece I sold to Cracked magazine: