Back before they began living together she would drop by his loft in the afternoon when she got off work. He had been working on the same painting for weeks. It never seemed to change though. He had hundreds of paintings stacked around his studio so he must finish them sometime. Occasionally she would arrive to find that he had painted over parts he had already finished--sanding some or most of the panel smooth and putting on a fresh coat of primer until that portion looked like it had never been painted on. Then he would repaint it exactly the way it was before.
It wasn't until they were living together that she realized he had painted the same picture more than thirty times.
He found a gallery that agreed to show 16 of the identical paintings. None of them sold. The gallery went out of business a few weeks later.