To understand the original masthead you have to know how “Unripe” was born. Back during the height of the internet bubble, I read about how people were rushing to buy internet domain names that were dictionary words. By the time I finally got around to doing this myself, all the words were gone, except for “unripe”. It was the last word picked. No one wanted it because “unripe” is a totally useless word, as far as Internet domains go. I bought it and it took 4 years for a use to come.
Finally the idea to publish obscure cartoons that had to ripen in the mind of the reader was suggested to me, I think as a joke. Such an approach would have to violate every known rule of humor. The challenge was to still try to be funny while breaking the rules. I wish now the joke had to do with unripe wine vintages, or something like that.
When it came time for the masthead I thought of the Droste Effect. This is an image that contains itself. This recursive process is a lot like the concept of thinking (ripening) and all that Hofstadter strange loop stuff.

good work!