This came about during a semi-private painting class I was teaching. One of the kids had two bits of news - one, that she got braces, and two, that she and her family were going on a cruise to the Caribbean. I commented that she was going to go sailing like a pirate, when her friend said "Pirates don't wear braces." I called Nonsense! and said that all you'd have to do is add braces to the skull on the Jolly Roger.
So while they painted their assignment, I painted this.
In part, it was just because I loved the idea. But also, I finished this in a half an hour, while walking around and critiquing their work. I made it part of the lesson - all the kids in the class were getting too particular, and trying to make just one spot perfect. I wanted to show them that they needed to loosen up and paint more freely. Always time to clean things up later, just get paint on canvas. Besides, it was an acrylic paint class, the more you mess up early, the more layers you have, and the final result looks richer in the end.
And here is the pre-teen pirate herself, posing with the painting: