On the Volokh Conspiracy they are discussing songs about obsession, but they seem to have missed the obvious "Every Break You Take" by The Police.

BTW, I think that Tyler Cowen is confusing Buddy Holly's "Every Day" with his "That'll Be the Day".

For my money, the best song about obsession is Tom Waits' "Alice":

It's dreamy weather we're on
You waved your crooked wand
Along an icy pond with a frozen moon
A murder of silhouette crows I saw
And the tears on my face
And the skates on the pond
They spell Alice

I disappear in your name
But you must wait for me
Somewhere across the sea
There's a wreck of a ship
Your hair is like meadow grass on the tide
And the raindrops on my window
And the ice in my drink
Baby all I can think of is Alice

Arithmetic arithmetock
Turn the hands back on the clock
How does the ocean rock the boat?
How did the razor find my throat?
The only strings that hold me here
Are tangled up around the pier

And so a secret kiss
Brings madness with the bliss
And I will think of this
When I'm dead in my grave
Set me adrift and I'm lost over there
And I must be insane
To go skating on your name
And by tracing it twice
I fell through the ice
Of Alice

And so a secret kiss
Brings madness with the bliss
And I will think of this
When I'm dead in my grave
Set me adrift and I'm lost over there
And I must be insane
To go skating on your name
And by tracing it twice
I fell through the ice
Of Alice
There's only Alice

It's his best album as well, and I don't say that lightly.