In the book Pollyanna, the Glad Game is a game the young, penniless orphan plays to make herself feel better about her shitty situation. Whenever something bad happens, she always considers how it could be even worse. Example:
-Oh no, I wanted a doll, but I've been given a pair of crutches!
-Oh well, I should be glad that I'm not a cripple who would need these crutches!
Ingenious right? Personally I prefer to find positive aspects in my own life when trying to feel a little gladder, but you know how it is, sometimes you just can't see the light. Even then, it can be irritating to have other people tell you that you're basically just whining and your problem doesn't mean anything. Nevertheless, it is admittedly easier to think of more negative things, than anything positive... and sometimes it may even provoke a little glad glee.
Since I prefer not to be gladly gleeful that I'm not starving in the third-world or suffering from a debilitating illness, I like to look to fiction for my own dose of misery. Here's my list. I'll slot any super-duper suggestions you make along with them for an even more comprehensive list:
Lord of the Flies by William Golding. Starting off as a happy little adventure story about some boys who are all excited because they are stranded on a sunny, pretty island with no grown-ups. By the end they're killing each other and weeping for the 'darkness of man's heart'. In addition, I get all depressed when I read it because I know it involves writing about it in an exam.
Revolutionary Road: the trailer. Depressing book of course, but I think the trailer really takes the biscuit. They pretty much decided to remove any hint of joy in the novel/film in order to try to make people watch it. Maybe they're counting on misery-lovers like me? Good luck to them!
Hallelujah. I'm not going to pick an example, because we all know that everyone has their own personal favourite with this song. But let me simply quote from this guy with the impressive vocabulary: The titular refrain is one of the most halfhearted exclamations you'll ever hear, a commemoration of all pyrrhic victories. The X-Factor cover itself is additionally depressing because it is so awful.
Romeo + Juliet. There never was a tale of more woe, than that of Juliet and her dear Romeo. PLUS you get to feel all depressed because somehow you haven't yet managed to bag yourself a Romeo. Oh wait, no... I'm not playing the game right.
As you can see, sometimes My Glad Game can descend into a bit of a miseryfest. But an additional plus, which I haven't even mentioned yet, is that fantastic artists don't tend to enjoy creating happy masterpieces. So in indulging in some gloom, you're also handily adding to your intellectually impressive list...