Anything by Antony and the Johnsons. Antony Hagerty tackles some very hard, very deep and choking feelings and events. This year, the big one for me was his song "The Spirit Was Gone", which is about seeing someone's body after they die and having to acknowledge that they aren't there anymore.

A few songs have always brought me to tears:

Natalie Merchant - My Skin
I recommend everyone hear this song at least once. Everyone's been at a point where they wonder if they're just ugly or worthless, and if they're only ever meant to be a discard; as if they will only ever sit on park benches and watch the world fall in and out of love at its whim, attempting to care for the happy couples in the vague daydream that they can be like them too. This song is for the bruised and broken from love, and it's my favorite get-it-out-of-my-system-and-just-break-down song.

Sarah McLachlan - I Love You
A good song about wanting to love someone you feel is always just outside your reach.

Capercaillie - Ailein Duinn (Dark-Haired Alan)
A classic lament from Ireland about a young girl whose lover is killed at sea, so she lies on the shore from which he sailed and vows to return to him in death. This is one of the most beautiful works of music I've ever heard.

Bulgarian Folk Song "Malka Moma" ("Little Girl")
When I first started learning bulgarski this year, I was introduced to this song by my friend who was serving in the Bulgarian military and helped me learn more about Bulgarian culture. This song is about a little girl praying for God to give her wings so she may soar above the land and sea to find the one she will love someday. Very sweet song.

"Zaydi, Zaydi Yasno Slance" (Go Down, Go Down Bright Sun)
I still have no clue whether this song is originally from Macedonia or Bulgaria, but it is one of, if not the most famous and widely performed folk songs in Bulgaria. The song is sung to nature from the perspective of a person who is dying, and the singer is telling the sun that when it sets it will always rise the next morning whereas when he/she lies down to sleep he/she will not rise the next morning. Very heartbreaking song; it makes you consider your own mortality.