Billy Joel - "The Downeaster Alexa"
The story it tells is quite a ballad, and I'm sure many a New Englander can relate. The video does a good job of portraying the setting and the stereotypical crusty characters, too.
Johnny Cash - "Hurt"
You knew this one was going to be in this list. Johnny Cash tears a song from Trent Reznor's grip and remakes it in his own image, turning Reznor's nihilistic lyrics about ending the present upside-down and instead making the song one of how badly Cash wants the past to return.
(this version has waaaay too many annotations, but fortunately they can be turned off)
And speaking of hurting...
Tom Smith - "A Boy and His Frog"
This song frequently wins...nay,
shuts down just about every "saddest song evar" competition when it shows up. If you're 25-50 years old, enjoyed movies like
The Dark Crystal or
Labyrinth, know who Emmet Otter is, if you can't count to 12 without
humming the tune, or without lightning crashing to your maniacal laugh once you get there...this song
aches. It aches so bad that YouTube viewers have actually flagged it enough to get it age-restricted.
I'll post a few more when I can remember what they are. I know there have to be a couple more nagging at me.
--Patrick