A song that's made me cry is Demi Lovato's 'Sober.' Personally, I have been fortunate enough to never have dealt with drug addiction, but this song still tugs at my heartstrings. Not only does the amount of emotion and sorrow in her voice overwhelm you with a wave of despair, but the lyrics really tell her story of her struggle with drug abuse. It made me cry my eyes out the first time I heard it. It's a really good song, and if you want to listen to some sad songs on a rainy day, I definitely recommend this.