What Makes A Compulsive Song Compulsive?

Right now I am listening to Okkervil River's Calling And Not Calling My Ex from their latest album, the Stage Names. (The embedded YouTube vid above is, in fact, a live recording of the song.) I have been listening to this song a lot. And by a lot I mean maybe three, four, five times a day, whenever I find a spare moment.

Now it doesn't take a Master's in psychology to figure out the etiology of this compulsion. I have been thinking a lot about an ex of my own. But we might find some interest in the details. What first drew me to the song was the line "I'm feeling pretty stupid now for ever having said goodbye." Which is exactly how I feel when I'm feeling, well, however it is that I feel. The sympathy I felt at that line made me stop, rewind the song, and start to listen again. Now, one way of explaining great art says that great art expresses what we otherwise find inexpressible. That great art alone can express these feelings because those feelings are too refined to be explained by our own poor powers of expression. But the emotions I find reflected in the song remain unexpressed by me, not because they are too ineffable or complicated, but because they are too cliched, too mawkish. I miss you. I never wish I said goodbye to you. The beauty comes from a simple sentiment, expressed simply, but a sentiment that if I actually said it would encourage my friends wonder whether I had turned emo on them. (Maybe, perhaps, I have.)

This has led me to think about obsessional songs. My housemate is currently listening over and over again to a verse by the British hip-hop legend Jehst (his verse starts at 1.10). In my sophomore year of college I listened to Mirah's song Mt St Helens every single morning when I woke up, much to the chagrin of my roomate, who at first hated the song, then grew to despise it, silently, while still in bed, trying to sleep, every day. (The song's first lines, "From the morning when I rise from my bed / to the evening when I lay my head in slumber" outright encouraged obsession--indeed, the song was compulsive because it was about compulsion. I blame you, Mirah, for mornings of moody music-listening, and for the discomfort you caused my roomate.)

These songs, I think, are just proxy obsessions: in my case, I am trying to find some way to channel my care for girls who, for whatever reason, are far away from me. In my housemate's case, he listens to Jehst ten times in a row because he is obsessed with the sheer skillful exuberance of the English language, with hip-hop, with speech.

Which is a little healthier, perhaps.

I don't know if what I'm talking about here is the already much talked-about earworm, but I suspect there is some difference. The earworm comes into your head unbidden. These songs, you invite them in.

I had first planned these paragraphs as an introduction to an open thread, and so will conclude:

TL;DR: What songs are you obsessed with, and why?