David Gray/Tear Jerker

The song "The Other Side" is so devastatingly depressing and beautiful that people during his live concerts have been known to start crying when he plays it -- in which he takes the sadness of the original, adds a healthy dose of catharsis, and comes out as Awesome Music. The fact that Gray himself seems close to breaking down at points while singing it just increases the effect. In fact, most of Gray's songs are known to do this.
- Then you learn that the song is about David mourning for the death of his father, whom he was very close to -- and each and every song off of A New Day at Midnight takes on a new level of poignancy and potency.
"Kathleen" is particularly heartrending, but some lines are particularly so.

Cars that sound like waves that are breaking
On some desolate shore
Stared so long into the great achin' sky
Seems like I wasn't there no more

"Ain't No Love" is about a guy who has been so numbed by his life that he can't feel anything, even for his child.

Some days I'm bursting at the seams
With all my half remembered dreams
And then it shoots me down again
I feel the dampness as it creeps
I hear you coughing in your sleep
Beneath a broken window pane

"Nos da Cariad" is about running away from the inevitable even while knowing it's coming.

The sun above the cotton grass
Is sinking down like lead
The seagulls know the truth of it
And scream it overhead

Then there's "As I'm Leaving".
"Babylon" ends on an upbeat note, but everything prior to that is just so downtrodden. It doesn't help that the music sounds almost exactly like a rainy day.
"The Old Chair" which David admits ties into thoughts he's had about his older relatives and what's going to happen to them, and he actually seems to get choked up when he talks about it in the video.