Even though it doesn't have a winning / losing condition, I had coded an automated bot[0] to draw for me in Doodle or Die[1]. Stopped using it when people started complaining though. It was supposed to be quick and dirty, that's why it's a windows forms application. But of course I kept improving it for a while. After implementing a very basic plug-in system, I realized I was spending too much time on it =) Here's an example drawing from a friend of mine, using my tool: http://doodleordie.com/c/EGXBBJeMU45#2
[0]: https://github.com/egeozcan/DrawThatThing
[1]: http://doodleordie.com