I love so many of the songs already suggested, like Adele's Someone Like You, ALL of those Ani DiFranco songs (who knew this board would have so many Ani fans?), Fleetwood Mac, etc.
Here is a great David Gray song called Shine:
https://www.youtube.com/watch?v=FAIcMg8zz6k
I can see it in your eyes what I know in my heart is true
That our love it has faded like the summer run through
So we'll walk down the shoreline one last time together
Feel the wind blow our wanderin' hearts like a feather
But who knows what's waiting in the wings of time
Dry your eyes, we gotta go where we can shine
Don't be hiding in sorrow or clinging to the past
With your beauty so precious and the season so fast
No matter how cold the horizon appear
Or how far the first night when I held you near
You gotta rise from these ashes like a bird of flame
Step out of the shadow, we've gotta go where we can shine
For all that we struggle, for all we pretend
It don't come down to nothing except love in the end
And ours is a road that is strewn with goodbyes
But as it unfolds, as it all unwinds
Remember your soul is the one thing you can't compromise
Take my hand, we're gonna go where we can shine
(And look, and look)
Through the windows of midnight
Moonfoam and silver
I also love Dan Bern's Baby Bye Bye:
https://www.youtube.com/watch?v=waUmHGxBAj8
Listening to the big guy's new CD laying in bed
The one his producer thinks he never shoulda made
But it gets me going, gets me into the shower
What a shock to be awake at this early hour
And you're gone, it was time to fly
And all that's left is the fact we tried
So thanks for the tunes, and thanks for the time
You're gone now, baby bye bye
Them guys from Orange County, man, do they wail?
Shakes my brain and it shakes my tail
New girl on top of me, will this work out?
I retreat to the kitchen and sort it all out
Chorus
You left your keys on the table
And on the bed you left a rose
And a note that said, "My CD's won't fit in the car
You can keep 'em I suppose"
This disc was left out in the sun, it's warped and it's hissing
I can't place the voice and the insert's missing
I turn off the phone so if you don't call it's all right
And maybe I won't listen to nothing tonight
Chorus
Also I am currently sort of obsessed with Kanye West's Runaway:
https://www.youtube.com/watch?v=L7_jYl8A73g