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1* "Hallelujah" from ''Music/VariousPositions''. It's been CoveredUp a lot.
2-->"And love is not a victory march\
3It's a cold and it's a broken hallelujah".
4
5-->"I did my best, it wasn't much,\
6I couldn't feel so I tried to touch,\
7I told the truth, I didn't come to fool ya.\
8And even though it all went wrong\
9I'll stand before the Lord of Song\
10With nothing on my tongue but hallelujah."
11** The version by Music/JohnCale, used in ''WesternAnimation/{{Shrek}}'', is particularly gut-wrenching.
12** [[https://www.youtube.com/watch?v=tfpVq4rPfQg Alison Crowe]] sings a heartbreakingly beautiful version of "Hallelujah" as well.
13** See TearJerker/ReginaSpektor for her version.
14** And TearJerker/JeffBuckley for his version.
15** And TearJerker/{{Voltaire}} for his.
16** Add Music/AxelRudiPell's [[https://www.youtube.com/watch?v=wKMP81DVLLk version]], in its own way.
17** The apogee would have to the be the version turned out by the contestants and judges on ''Series/TheVoice'' in tribute to the Sandy Hook victims.
18** Add Creator/KateMcKinnon's gut-wrenching [[http://www.usatoday.com/story/life/entertainthis/2016/11/13/saturday-ngiht-live-kate-mckinnons-hillary-clinton-delivers-tearjerker-hallelulah-performance/93755628/ version]] on the November 12, 2016 episode of ''Series/SaturdayNightLive'', following the election of Donald Trump.
19** The most devastating of all may very well be the [[https://www.youtube.com/watch?v=D0Lm8-C6xnU version]] that [[Music/LinkinPark Chester Bennington]] sang for the funeral of Music/ChrisCornell. It isn't just the fact that the song was done in tribute to a rock legend gone far too soon, but also that Chester himself committed suicide less than two months later.
20* Another Cohen song would be "Stranger Song" from ''Music/SongsOfLeonardCohen''.
21--> ''And then leaning on your window sill\
22he'll say one day you caused his will\
23to weaken with your love and warmth and shelter\
24And then taking from his wallet\
25an old schedule of trains, he'll say\
26I told you when I came I was a stranger\
27I told you when I came I was a stranger.''
28** [[https://www.youtube.com/watch?v=RLq7Aqd_H7g Heck, he tears up while performing it live!]] That's how tragic his songwriting can get.
29* "Anthem" is also heartbreaking:
30-->"The wars they will be fought again\
31The holy dove, she will be caught again\
32Bought and sold and bought again\
33The dove is never free"
34** But the chorus of "Anthem" has been known to bring [[SugarWiki/HeartwarmingMoments tears of an entirely different type]]:
35-->"Ring the bells that still can ring\
36Forget your perfect offering\
37There is a crack, a crack in everything\
38that's how the light gets in..."
39* "Bird on the Wire" from ''Music/SongsFromARoom'', sad all the way through, but contains what is going to be L. Cohen's epitaph:
40--> ''Like a bird on the wire\
41Like a drunk in a midnight choir\
42I have tried, in my way\
43To be free''
44*
45--> ''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.''
46--> ''Everybody knows the boat is leaking. Everybody knows the captain lied. Everybody got this broken feeling like their father or their dog just died.''
47* "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."
48* "Famous Blue Raincoat" from ''Music/SongsOfLoveAndHate'' is widely considered to be one of the most depressing songs ever written. "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..."
49** Pretty much the entirety of Music/JonathanCoulton's version, surprisingly.
50* "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."
51** And ''especially'' when it plays in Film/PumpUpTheVolume, where it is played as a heartwrenching reaction to a suicide.
52* "Tower of Song": With plentiful GallowsHumor.
53--> ''I said to Music/HankWilliams, "How lonely does it get?"''
54--> ''Hank Williams hasn't answered yet,''
55--> ''But I hear him coughing all night long,''
56--> ''A hundred floors above me, in the tower of song.''
57* The beautiful and epic "Death of a Ladies Man."
58** "The man she'd wanted all her life was hanging by a thread/I never even knew how much I wanted you, she said..."
59* "The Story of Isaac" from ''Music/SongsFromARoom'', full stop. ''I was running, he was walking, and his axe was made of burning gold.''
60* "Suzanne" from ''Music/SongsOfLeonardCohen''... It's not even necessary to quote anything. The nostalgic lyrics with the melancholic guitar, the Jesus parable, and Cohen's background for the song. Just sad.
61* "Are you the teachers of my heart?" ''"We teach old hearts to break."''
62--> ''I was handsome, I was strong''
63--> ''I knew the words to every song''
64--> ''Did my singing please you?''
65--> ''No, the words you sang were wrong.''
66* "Winter Lady" is a perfect marriage of bleak lyrics and bleak music. It's easy to see why Creator/RobertAltman chose it for the ending of ''Film/MccabeAndMrsMiller''.
67* The entirety of his final album ''You Want It Darker''. Leonard knew his time was up by this point, and it's reflected here. ''Especially'' in the reprise of "Treaty" at the end of the album. If you weren't crying for the rest of the album, this will do it.
68--> ''I wish there was a treaty we could sign\
69It's over now, the water and the wine\
70We were broken then but...now we're borderline\
71And I wish there was a treaty...\
72I wish there was a treaty...\
73Between your love...and mine''
74** The title song, "You Want It Darker", bleakly accuses God of "want[ing] it darker" while recalling the Holocaust ("A million candles burning for the help that never came... They're lining up the prisoners/And the guards are taking aim/I struggled with some demons/They were middle-class and tame") and quotes the Mourner's Kaddish ("Magnified, sanctified/Be Thy holy name"). If that won't get you tearing up, there's also Leonard singing "Hineni, hineni/I'm ready, my Lord" ''two weeks before his death.''
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