I hereby nominate Delta Dawn.
Forgot one…La Cienega Just Smiled by Ryan Adams. About having to choose between two lovers.
“And I hold you close in the back of my mind
And raise my glass 'cause either way I’m dead.
Neither of you really help me to sleep anymore
One breaks my body and the other breaks my soul
La Cienega just smiles as it waves goodbye.”
I was going to post this one, too. I swear, Ben hauls in the 6/8 signature and it’s like he’s never been anything BUT heartbroken.
another one: Stabbing Westward’s What Do I Have To Do?
“Neither One of Us Wants to Be the First to Say Goodbye” - I have the version by Gladys Knight and the Pips.
There can be no way
There can be no way
This can have a happy ending
So we just go on
Hurting and pretending
Convincing ourselves to give it just one more try
“Hope Alone” - Indigo Girls
You’re a land of secrets, its only citizen
And though I paid my dues I was never allowed in
And so I am a stranger especially today
I get sad and lonely and you get your way
You were looking for your distance and sensing my resistance
you had to do your will
I had to learn the hard way
We were just an empty dream too big for hope alone to fill
St Swithin’s Day by Billy Bragg. Billy can sound sad singing happy songs though.
Do You Realize? by the Flaming Lips. Though it’s not really sad when you think about it. I had a loverly chat with Wayne about this song in person (brag brag brag) and I wish I could post a transcript here because it was really cool.
Aimee Mann’s Wise Up , from the Magnolia sountrack. Maybe not strictly a love song. But damn, can Aimee write.
I love sad songs.
My weepiest is “Maggie” by Colin Hay (former lead singer of Men At Work). He’s loved her all his life, but only found out she loved him back from the suicide note she left:
I hadn’t heard from you in years
And then your mama called
She couldn’t speak for tears
She said you left me a note
Inside my pocket burns
With these words you wrote
Another one where the straight lyrics don’t do the sadness justice, you have to hear it.
FlyingDragonFan, I love Colin Hay! And I agree on Maggie.
These are some songs that aren’t necessarily, nor strictly, sad love songs. They are kind of reflexive or conditional love songs depending on how you look at them. I think they are pretty sad, lyrically and musically and they all have a certain ambience and style that you can tell comes from the artist’s heart, lots of Emotion.
Uncle Tupelo- Fatal Wound
Fuel-Shimmer
Beck-Lost Cause
Audioslave-Shadow On The Sun
These are some love songs that I think are sad, but are more conventional and less apocryphal.
Ramones-I Remember You
Everything But The Girl-Missing
Vertical Horizon-Best I Ever Had
Jim Croce’s “Time in a Bottle” always makes me think of the one that got away.
I Can’t Make You Love Me by Bonnie Raitt is just devastating:
I’ll close my eyes then I won’t see
The love you don’t feel when you’re holding me
Morning will come and I’ll do what’s right
Just give me till then to give up this fight
And I will give up this fight
Blues As Blues Can Get by Delbert McClinton:
Gonna sit right down in my easy chair
Pull out a deck of cards, play some solitaire
Break out a bottle, wash me a glass
To keep me company 'til the feelings pass
Everybody needs something to do
Me, I’ll just sit here and think about you
It might seem hopeless, but it ain’t that bad yet
It’s just the blues as blues can get…
Cole Porter’s Night and Day - super sad version by Bing Crosby…
In the roaring traffic’s boom
In the silence of my lonely room
I think of you…
Night and Day
Good for just blubbering to…
A lot of her songs on “The Forgotten Arm” are incredibly bittersweet and sad when you listen to them carefully. I especially like “Goodbye Caroline,” which you can listen to here:
http://www.aimeemann.com/theforgottenarm.html
It’s hard to pick just one.
You Were Mine by The Dixie Chicks:
Lyin’ Eyes by The Eagles:
My Immortal - Evanescence:
Something I Can Never Have - Nine Inch Nails:
Hurt - Johnny Cash, also Nine Inch Nails did the original:
Every Rose Has Its Thorn - Poison:
I Know You’re Married (But I Love You Still) - Patty Loveless & Travis Tritt, plus many other artists:
*Up Where We Belong * (music Jack Nitzsche and Buffy Sainte-Marie, lyrics Will Jennings) is from An Officer and a Gentleman (1982). Joe Cocker and Jennifer Warnes performed the hit version, but there is another version that convinced me the song is religious in its essence. It’s also a song that bridges the religious/secular chasm to the complete satisfaction of whichever type of listener.
The religious version I am familiar with is by BeBe and CeCe Winans. The first line is changed slightly from Cocker’s “Love lift us up where we belong,” to Winans’ “Lord lift us up where we belong.” I once (probably in the 1980’s) saw a performance of it on Jim Bakker’s PTL (Praise the Lord) Club, sung with such feeling and fervor that it choked me up, at a time I had no religious leanings.
Joe Cocker tries to sound African-American, but when you witness a black man sing this song with feeling it is truly impressive.
Aha! you’ve inspired me to make a “sad songs” playlist.
I live my iTunes. 
Peace,
mangeorge
I gotta submit Jerry Lee Lewis’ “She even woke me up to say Goodbye”
It’s not that they don’t want to be together, they can’t. What makes it even better is we don’t know why. Just that she couldn’t handle the stress of the relationship.
SSG Schwartz
Largely because of a personal experience;
“Lips of an Angel”, by Hinder. the yrics
What sometimes happens when you do choose to “Love the One You’re With”. And don’t we all.
Warren Zevon’s Hasten Down the Wind
She’s so many women
he can’t find the one who was his friend… 
Hm, I have three that always make me feel sad.
“Carelessly”, when sung by Billie Holiday. About throwing aside someone who loves you truly, maybe because it was too “easy,” and realizing later what a mistake it was.
Another is “Artichoke” by Cibo Matto. This is one you really have to listen to, but it’s very haunting, and conveys such a sense of longing. It really captures that feeling of being in a relationship with someone that isn’t going anywhere, and you just can’t understand how to end it, of even if you should, and it’s eating you up.
But my favorite (drumroll!) is “Pissing in a River” by Patti Smith. It’s not “sad” in the most conventional sense (Patti rocks too hard for that) but it’s one of the most true songs I’ve ever heard about the anguish of being left by someone you love.
When her voice fades out at the end, oh! You just feel it! She’s so enraged, but it’s all so hopeless.