Motherfuck. I've seen my Dad sing that at a few funerals when I was younger. That context keeps it from being romantic. Unless you're more twisted than I thought.
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“This is going to become a bad meme,” Todd observed.
There are several songs of a religious nature that do it for me.
Estrella -- Brave Saint Saturn
The author sings about struggling with faith while simultaneously watching his friend, who is dying from a degenerative disease, never lose faith. It was written as a tribute to him after he passed. It is beautiful and haunting.
I could list a bunch of Brave Saint Saturn songs. The band was a side-project of the band Five Iron Frenzy, which is known for its upbeat tone. BSS was meant to channel the darker themes that wouldn't really fit.
I'll give one more:
Invictus -- Brave Saint Saturn
A big theme throughout the band's works is of bitterness, cynicism, and depression being represented by darkness and God represented as light breaking up the darkness. I love this song because he just really bares himself, and it really speaks to me when I'm in low places.
I know there are other songs that are not religious that make me cry, but they're just not coming to mind right now.
I'm sorry, maybe I missed it, but is not one motherfucker going to list the saddest (And frankly, best [either this or B.o.B., anyways]) song of the aughts--if not ever?