I was wondering if there are such examples of feats of programming. There is obviously TempleOS, which is even mentioned in the wikipedia page of outsider artists.
Dozens of UI elements. Nothing on the screen aligned. Nothing was in a logical place. Related items were not grouped together. Buttons had labels like 'Button1', 'Button1_'. The tab-order was completely random, so you had to use a mouse exclusively. It was a horror show.
The code underneath was just as crazy. The system was used day-to-day by several people who just understood its quirks. I made the fix I needed to make and got the hell out of there.