Adrift (1994)  Done on an IBM PS1 Windows 3.1 using Microsoft Paint that was included on this computer (my first computer).

After I completed this image — very meticulously, pixel by pixel in many places, over a period of many days — my computer crashed and completely destroyed the file. I was devastated. But, I decided to start all over again, and this one is the result. Who knows whether or not it is better or worse than the first? But one of the biggest problems with those early computers — and there were many problems — was that they would unexpectedly crash, destroying whatever you were working on.