Leonard Cohen/Tear Jerker

"Hallelujah". It's been covered by virtually every artist in existence.

"And love is not a victory march
It's a cold and it's a broken hallelujah".
"Maybe there's a god above,
and all I ever learned from love
was how to shoot somebody who outdrew you."
"And even though it all went wrong
I'll stand before the Lord of Song
With nothing on my tongue but hallelujah".

- The version by John Cale, used in Shrek, is particularly gut-wrenching - and probably more affecting than the Rufus Wainwright version on the soundtrack album. Of course, when you're talking about this song, it's all relative...
- Alison Crowe sings a heartbreakingly beautiful version of "Hallelujah" as well.
- Imogen Heap's heartbreaking a capella version must be mentioned.

"The wars they will be fought again
The holy dove, she will be caught again
Bought and sold and bought again
The dove is never free"

- See Regina Spektor/Tear Jerker for her version.
- And Jeff Buckley/Tear Jerker for his version.
Another Cohen song would be "Stranger Song".

"And then leaning on your window sill
he'll say one day you caused his will
to weaken with your love and warmth and shelter
And then taking from his wallet
an old schedule of trains, he'll say\\I told you when I came I was a stranger
I told you when I came I was a stranger."

- Heck, he tears up while performing it live! That's how tragic his songwriting can get.
"Anthem" is also heartbreaking:

"The wars they will be fought again
The holy dove, she will be caught again
Bought and sold and bought again
The dove is never free"

- But the chorus of "Anthem" has been known to bring tears of an entirely different type:

"Ring the bells that still can ring
Forget your perfect offering
There is a crack, a crack in everything
that's how the light gets in..."

Bird On The Wire, sad all the way through, but contains what is going to be L. Cohens epitaph:

Like a bird on the wire
Like a drunk in a midnight choir
I have tried, in my way
To be free

Everybody knows the dice are loaded. Everybody rolls with their fingers crossed. Everybody knows the war is over. Everybody knows the good guys lost. Everybody knows the fight was fixed. The poor stay poor; the rich get rich. That's how it goes; everybody knows.
- Everybody knows the boat is leaking. Everybody knows the captain lied. Everybody knows this broken feeling like their father or their dog just died.
"I'll try to say, a little more - love went on and on; until it reached an open door - then love itself, love itself was gone."
"And what can I tell you, my brother, my killer, what could I possibly say? I guess that I miss you, I guess I forgive you, I'm glad you stood in my way..."
- Although, these lines from "Famous Blue Raincoat" may be even worse: "Thanks for the trouble you took from her eyes; I thought it was there for good, so I never tried." Then it's bam! Tears welling up every time.
"If It Be Your Will" in its entirety, but especially: "Let your mercy spill on all these burning hearts in hell, if it be your will, to make us well."
"Tower of Song": "I said to Hank Williams 'how lonely does it get?'/Hank Williams hasn't answered yet/But I hear him coughing all night long/A hundred floors above me in the tower of song..."
The beautiful and epic "Death of a Ladies Man."
- "The man she'd wanted all her life was hanging by a thread/I never even knew how much I wanted you, she said..."
"The Story of Isaac", full stop. I was running, he was walking, and his axe was made of burning gold.
Suzanne... It's not even necessary to quote anything. The nostalgic lyrics with the melancholic guitar, the Jesus parable, and Cohens background for the song. Just sad.