There is a thought that ‘Every Breath You Take’ by The Police is the creepiest pop song of all time.
(Of pop songs that can be played on the radio, that is.)
It is not.
The creepiest pop song is, without a doubt, Cliff Richards’ ‘Living Doll’.
Kids, if your folks (or even Grandparents, in this case) tell you they don’t write songs like they used to, just ask them to explain these lyrics:
I’m gonna lock her up in a trunk
So no big hunk can steal her away from me
A cover of this was playing at Woolworths today.
Here’s Cliff Richards and The Young Ones on Youtube.
mgpcpastor's blog 
Well, you have lead a protected life 🙂 Consider e.g. some of Eminems works. (Possibly, depending on definitions used, not pop, but still…)
A favourite creepy song of mine is the Everly Brothers’ All I Have to Do Is Dream, which could be interpreted as anything from very sweet to deeply creepy, depending on the exact circumstances. (Incidentally, I believe, with a Cliff Richard cover.)
Good call on the protected life.
Also a good call on ‘All I Have To Do Is Dream’.
But I’m not expecting Eminem covers to start getting played as background music in our local supermarket anytime soon.