I'm one of those people who needs complete and total silence to fall asleep so there really isn't a song that makes me fall asleep to. However, there are some songs that are better to fall asleep to than others. One of the better songs happens to be "Winning" by Emily Haines and the Soft Skeleton. I've said it before and I'll say it again: Emily has an AMAZING voice. Normally, with Metric, she sticks to harder, more rock style music. In her solo music, on the other hand, she had the chance to show off just how beautiful her voice is with a bunch of slower piano music. This song is incredible and features of of Emily's amazing lyrics.
On the topic of sleep, sleep is one of my favorite things ever. I wouldn't mind being in a coma... as long as I wasn't secretly conscious and just couldn't express myself. Cause that'd suck. And not being able to shower would suck to cause I'd staaaaank. Anyway, off the topic of comas and into regular sleep... It seems no matter how much I sleep, I'm always tired and I always want more. Perhaps I'm lazy. Or I just have really weird sleep needs. Or I'm dying... Hopefully not that last one o.O
Also: This song isn't on the site I make my playlists on so I put another song by Em on there. Here's a video of it live, though.