I have to say that I really enjoy those songs out there that are positive and yet at the same time melancholic. Examples include "What a Wonderful World" by Louie Armstrong and "Have Yourself a Merry Little Christmas". It's those kinds of songs where you could see someone putting it on to try to make themselves feel better, but instead just start weeping by the end.
Really, I think the whole reason I say this is because I think this might quite possibly be the funniest thing in life. Just that attempt by someone whose life has not turned out ideal and then some song just makes them lose it. And as you watch them and their visage crumble, there is this light melody that is supposed to comfort them. It can be touching. But depending on the person, it is hilarious. Like some guy has spent the last four years trying to get on some lame lacross team and he goes to the list and sees that he's cut and as he's driving home in his pimped out SUV that his parents paid for and his summer mix CD comes something like "Somewhere over the rainbow" comes on and as he sings along he catches a line and just loses it and says outloud to his CD player something like "that's right, somewhere over that rainbow, my dreams will come true" and will just be a wreck of a human despite being the douche who was proclaiming that he was going to "show y'all" and then for the rest of his life overcompensating by becoming a bigger douche than before, but whenever he hears the song again, he begins to tear up a little again. Of course, he'll realize it and then when there's a girl he wants to bang, he'll get her in his truck and then preface playing this song by saying it's his favourite and it means a bunch to him and then while they listen to it, he kind of fakes the tears or at the very least gets that face where it looks like he was supposed to cry, but really he just looks like his is all gnarled up. Oh, and looks like he is forcing himself to cry. Key component to this guy as he tries to trick this girl into thinking that he has a sentimental side, and then depending on how dumb she is, she may fall for it. But if she doesn't, he just tries again with the next one.
When like some would-be actor who had like one or two good performances in college and then thinks he's the next Jim Belushi and the king of the mountain, but is confused when he is still just some slack-jaw working the graveyard shift on Christmas Day and is nowhere near family and then "Have Yourself a Merry Little Christmas" and finds himself singing the song to himself and then just crying softly next to the packs of cigarettes, realizing that his life is directionless and pathetic because it is ludicrous that he believes that he is unique and talented and will be the one who makes it compared the other million people who are currently in Hollywood who also believe that they are unique and talented and that they will make it.
Hilarious...man, what am I doing...I think I'm going to listen to Joe Purdy's "Wash Away" and let my tears gently put me to sleep.