Here's who made the running:
#25: The River by Bruce Springsteen:
Okay, I get that Bruce is a tormented soul and all that, but this is not a claw-your-eyes-out-with-grief song. This isn't even a turn-on-the-tears song. This is a "woops" song that might get one or two droplets out of you if you're completely wasted in a towny bar.
#24: Nothing Compares 2 U by Sinead O'
Oh, whatever! Break-ups suck, and the whole 15-days and 7 hours smells of fresh wounds (not to mention extreme codependency: see "went to the doctor"), but seriously? In a week, she'll have a new crush and she'll feel better. This is not dripping with lasting sorrow and torment. Even the wimpy violin solo is unconvinced. Don't even get me started on the "2 U."
#23: No Surprises by Radiohead:
What?! How did you manage to pick one of the most cheerful sounding Radiohead songs when they've given you dozens of other anthems to weep to? What about How to Disappear Completely? Exit Music? Or anything other than this song? Okay, so the lyrics could be construed as vaguely suicidal, but read up and then shut up. Not a sad sounding song anyway! There's a freakin' glockenspiel! Why are all these songs in major keys?
#22: A Change Is Gonna Come by Sam Cooke:
Is this, or is this not a Pursuit-of-Happyness-esque stick-to-your-guns-tiger song? See, to me this song is hopeful. Again, not so much with the sad. It's a shit-happens-but-it's-gonna-get-better song. I could not cry to this song.
#21: Space Oddity by David Bowie:
You have got to be kidding me. I... I can't even. No. Shut up. Everyone knows this song was an excuse to use kooky sound effects. Everyone. Don't pretend it has deep emotional impact.
#20: That's the Way I've Always Heard It Should Be by Carly Simon:
Okay, maybe. It's pretty tragic, and it's honest. I'll give you that, but it kind of demands a prerequisite of a crappy childhood due to marital problems between parents to get real heartfelt tears pouring. It is fairly hopeless, though.
#19: Lost Cause by Beck:
See Radiohead argument. This is Beck. We know he can groove the Sad Bastard tunes. Why don't you, oh, I don't know... pick one that applies to this list! As an artist, he should be on this list. This song should not. What is it with the Spinner Staff and bells?
#18: I've Gotta Get a Message to You by the Bee Gees:
Are you seriously trying to tell me this is a sad song while they're singing in falsetto? There are maracas involved. Honestly, leave the prison songs to Johnny Cash and the rest of the country genre. They know how to do it right.
#17: Back to Black by Amy Winehouse:
If this is a sad song, so is "I Will Survive" by Gloria Gaynor. Riiight.
#16: Shilo by Neil Diamond:
Um... This is an ode to an imaginary friend. And very upbeat. Again with the not sad!
#15: My Mom by Chocolate Genius:
Your mom!! Okay, okay. I'll give you this one. This is pretty sad. I think it's the specificity of it, and having seen the effects of Alzheimer's... it's pretty heavy.
#14: Anyone Who Had a Heart by Dionne Warwick:
... might cry at this song if the circumstances were juuuuust right. But it doesn't belong on this list.
#13: Naked as We Came by Iron & Wine
Acknowledging your own mortality is a difficult thing, but again it's too graceful and resigned to really be all that sad. Sorry.
#12: In the Wee Small Hours of the Morning by Frank Sinatra:
Ol' Blue Eyes was a charmer and all, but this isn't really a tear-jerker. He's got others.
#11: Brick by Ben Folds Five:
Granted. I agree. This would've been on my list. I've definitely cried to this song. I have a personal affinity for "Evaporated" as a weeper, but this one is loaded. Driving a high-school girlfriend to get an abortion the day after Christmas morning? Yeah.
#10: In the Real World by Roy Orbison:
Whatever. This is an anthem for a quitter. No pity parties here! In the immortal words of Tim Gunn, "Make it work!"
#9: Concrete Angel by Martina McBride:
Not many songs about there about child abuse, but as long as it's sung by Martina, I'm down. It's pretty tragic, even though the chorus is a little to cheerful for the subject matter, but that's just a gripe with the song. I'll let this one slide.
#8: Dance With My Father by Luther Vandross:
Yeah. This song is killer. Sappy, but again... hitting that parent mortality button. P.S. I love that this song occasionally refuses to rhyme.
#7: Hallelujah by well, Leonard Cohen, but Jeff Buckley for our purposes:
Dude, the Rufus Wainwright version would be on my list... but I this version just isn't my favorite, and I love me some Buckley. This one gets half approval.
#6: He Stopped Loving Her Today by George Jones:
Finally! A tragic country love song! It's great 'cause these guys actually cry on stage. My Pa would be proud. I don't know if it's #6 on the Saddest Songs of Ever OMG though.
#5: I Know It's Over by The Smiths:
This song is too drunk to be... oh wait, that's just Morrissey. Sorry. This song has always frustrated me. It's annoyingly futile. It begs the question, "so what?" So on those grounds, Shelby says, "NO!"
#4: Hurt by Johnny Cash:
I was wondering when he was going to show up. This is definitely one of the saddest songs ever, and one of my personal favorites. It's such a pure, somber confession.
#3: Eleanor Rigby by The Beatles:
I don't know that this is an exquisitely sad song. It's sad, sure... it's definitely not #3 of all time. I do love me some Beatles, though.
#2: Gloomy Sunday by Billie Holiday:
Okay, Billie rocked the blues. You could pick pretty much any song, and I'd sign on. But I think the song that belongs right here is Strange Fruit. That song has the capacity to make me physically ill with sadness.
#1: Chicken Wire by Pernice Brothers:
Okay, this is sad. It's The Virgin Suicides in a song, but AIR would've captured the mood better. In fact, they did. And they did it without elevator-music trumpet interludes! At any rate, this is not the saddest song ever, you fools. Boo!
What happened here? We have a whole genre of whiny emo kids singing about death and despair! We have the 70's anti-war anthems like "Seasons in the Sun"! We have a good wicker basket full of indie musicians who cryptically whine about woe! We have the other half of country music that isn't about trucks and horses! At least 7 of these songs had bells. What gives?
I'm gonna do this right. I'm gonna put together the saddest list there ever was. And you're gonna help me.
If you are able, please upload one - if not two or more - songs that make you cry like a baby. I'm talking snot-dribbling sobs, people. Heck, if we have to make an anthology, I'm game. It'll be Part One of my glorious return to el jay. It's on.