The key identity seems to be that both songs concern the death of a lover (or can be interpreted that way easily). Also, they have stylistic similarities which I will not try to describe.
Both song you mention are favorites of mine. If I were to make a mix with those two, I'd probably include the following, both for style and subject matter:
Bright Eyes' "Oh You Are The Roots That Sleep Beneath My Feet and Hold The Earth in Place" is probably the best fit, musically and thematically. posted by jeffmshaw at 8:14 PM on January 18 [1 favorite has favorites]
Sufjan Stevens - Casimir Pulaski Day
The Shins - Those to Come
Belle and Sebastian - It Could Have Been A Brilliant Career
Bonnie 'Prince' Billy - Missing One, or a few dozen other of his songs
Nickel Creek - Tomorrow Is A Long Time (covering Bob Dylan)
Emmylou Harris - Boulder to Birmingham
Beth Nielsen Chapman - Sand And Water
Alison Krauss & Gillian Welch - I'll Fly Away
The Innocence Mission - Snow
José González - Heartbeats (covering The Knife)
Red House Painters - Follow You, Follow Me (covering Genesis)
Emmylou Harris - Gulf Coast Highway posted by notsnot at 5:06 AM on January 19
"Almost Lover" by A Fine Frenzy
Nthing Bright Eyes. When you're ready to come out of your funk, look for "First Day of My Life." Sounds similar, but more optimistic. If the songs you mentioned are the death, then "First Day" is the rebirth. posted by Gotham at 10:07 AM on January 19
Some really amazing songs suggested - I might steal some ideas from this thread for myself...
Also - are you on Last.FM? Check out your neighbourhood - or the hive mind on there. Not to jump on someone elses post here, but do we have a group on Last.FM?
That might be useful. posted by mjlondon at 5:21 PM on January 19
Possibly the saddest song - tonally - I've ever heard is Jump Little Children's CATHEDRALS
http://www.youtube.com/watch?v=zsbQ2ZvFLn0
But I'm also a big fan Innocence Mission's cover of Moon River for sheer bumitude posted by rileyray3000 at 5:16 PM on August 11
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The National - "Fake Empire"
Tyler Ramsey - "A Long Dream"
Also see Bright Eyes and M. Ward
posted by Frank Grimes at 7:20 PM on January 18