Back in 1998, the world was a very different place. The WWW as we know it was very much still in its infancy, and many people dialled into the internet on an occasional basis rather than being always connected like they are today. There were no Smartphones, no apps, and back then we wrote applications that ran under Windows and didn't need an internet connection.
I was working as a Software Engineer, and someone sent me the Shakespearean Insult kit - which really was just a piece of paper with three columns, and you selected one from each column and preceded it with 'Thou' and that was your Shakespearean insult. Some sites credit Jerry Maguire of Center Grove High School, Greenwood Indiana, as being the originator of the list of words.
I thought it might be fun to code that into a simple Dialog-based application, and did so one afternoon, and that was autoinsult v1, which was released in May of 1998.
A few days later, I added the Modern style, which I based upon the style of insults generated by an old MS-DOS program called "Insults" from the Modern Advisory Institute, Utah, circa 1983. I massively extended the list of words, just adding them as they occurred to me - I have quite a large vocabulary and enjoy learning new words too.
Several weeks later I added the Arabian style, inspired by the phrase "May the fleas of a thousand dogs infest your armpits".
Finally, in September of 1998, a guy called Marcin Oseka contacted me and suggested the Mediterranean style, and suggested a set of phrases. I incorporated these into AutoInsult, and again extended them further.
At some point I discovered a website by a guy called Paul Levin which also generated the Arabian style. Paul was kind enough to send me his data for it, which I incorporated into AutoInsult.
Initially the application was released as Freeware, then in July of 1998 became Shareware (I didn't make a lot of money from it. Especially once it was cracked - it had the dubious honour of being the example program in a hacking tutorial!). In 2005 I made it Freeware again, not only because Shareware had fallen out of favour but also because I was fed up of trying to stay one step ahead of the hackers cracking it.
During the lifetime of the application, the features grew, with pop-up insults, timed insults, a tray icon, the ability to lock certain columns and regenerate the rest in order to zoom in on the ideal insult (something that Cyanide and Happiness now do on their random comic generator), and also Smart Indexing which made sure the same word or phrase was not used twice. It also let you do a dictionary lookup on words that you weren't familiar with (as it amused me to add some fairly obscure words to the dataset). I even worked on a version that used the Microsoft Agent to speak your insult to you, although this was never released.
However, with the rise of Smartphones, and the always-on internet, Windows applications very much fell out of favour. As a programming exercise, I wrote an Ajax-based web page with a MySQL database back end, to give a very basic implementation of AutoInsult, which I called WebInsult. It didn't have Smart Indexing, nor the ability to lock down columns.
Eventually, it was not worth maintaining the Windows Application, and I discontinued it. All that remains now is this website version, and AutoInsult has become a bit of a footnote in Internet history.