I tracked down and interviewed the co-founder of "Christian and Scott's Interactive Top Ten List," which was the place where some of the first jokes on the web were published. Started by two Stanford students in their dorm room in 1995, it ran topical lists like, "Top Ten Theories Explaining The Plausibility Of Toe Rings," and "Top Ten Benefits Of the Y2K Bug." They published 20,000 jokes over the course of 20 years. And luckily for all of us the page is still archived in its original from. http://www.csittl.com/
Christian even helped me search for the jokes I wrote as a 14 year old....