Something about Piano Man by Billy Joel always gets to me - and someone else mentioned it, but Johnny Cash's rendition of Hurt is another contender.

On a more obscure note, Karissa by Sun Kil Moon always gets me. It's an ode to a distant relative of his who passed away. It captures a really unique melancholic feeling, for me at least. It addresses how you feel when you lose someone close enough to you that it jars you, but doesn't destroy you. It's a unique mood I think most of us can relate to, but the way it's presented on this song is melancholic, haunting, and beautiful.

https://www.youtube.com/watch?v=GBNdOTu2Wn0


Cheers,
Deryk