No way would this work for me at all! I'm a very light and sensitive sleeper; it has to be quiet, the temperature just right and totally dark for me to sleep soundly. I'm also given to bouts of the dreaded insomnia, so listening to music while I sleep is a no-no. I mean do people even do that, and for what reason? It's not like they'd continue hearing the music as they sleep, is it? I don't personally see the point of it.
It depends on the type of music you're listening to. If you listen to classical, soft and mellow music, then it won't take long for you to fall asleep after a few minutes of listening to the tune. You don't listen to rock and alternative music when you intend to crash for the night. I used to do this when I was in my teens but stopped a few years ago after realizing how much I wasted electricity.
I used to listen to music right when i settle to bed but i mostly turn it off when I'm really close to dozing off. I think there's only a couple of instances where i woke up to my earphones blasting with music. But normally, i prefer sleeping peacefully.