Jack-O-Lanterns are so flexible. You can make them scary, merely spooky or kind of cute and almost cuddly.
Carving them is much messier than creating jack-o-lanterns in ASCII art.
An ASCII art jack-o-lantern is a good way to start your first try at ASCII art. Once you figure out the size and shape of your pumpkin adding the face is mainly placing lines and dashes. Of course, you can get fancier, more elaborate. Larger sized creations take more time (of course) but it’s more like filling in the spaces. Smaller ASCII art creations which require more thought about each individual character used and how it works with those around it.