A Mental Floss post mentioned the book Owl at Home, by Arnold Lobel who:
sets out to brew a pot of “tear-water tea”–and, naturally, in order to do so he must imagine and then dwell upon the saddest objects possible
This reminded me of a game Justin & I sometimes play with his brother Cory, called the "Sad Game". It started out one night before Thanksgiving when we were all driving up to a cabin in the mountains for a long weekend with family and, as we were zooming down the highway, we all caught a glimpse of a man sitting alone in a fast food restaurant. Justin said he bet the man was divorced, and I followed he probably wasn't allowed to spend time with his kids unsupervised. Cory quietly added that he was also an only child whose adoptive parents had passed away in a car accident. When he was a teenager, Justin finished. And so the "Sad Game" was born. Sad theories grow and grow until the listeners can't bear it anymore and beg for the game to end. I don't think any of have even read Owl at Home.