I got one of those flowery iMacs (1999?) when they came out. And that introduced me to the idea of making painterly style art on a computer. Which seemed pretty stupid and hey still does, but then that's never stopped me doing anything.
This is the first piece of digital art I made, aside from all the stuff I did in Melbourne Draw on my Speccy, then IconGraphix, then Dpaint 4 on me Amiga etc etc. This was made in Apple Works.