Not the most depressing, but the saddest. Not the same thing at all.
For me, it has to be Crying sung by Roy Orbison. Because, I think, it’s sooo real.
The first line “I was all right for a while” gets me.
Then we learn that she loves him, but not “that way”. And he still loves her, but for him it is “that way”.
Been there, eh.
And then, there’s those beautiful pipes.
Peace,
mangeorge
Billy Vera’s **At This Moment ** comes to mind.
Teen Angel by some unknown late 50’s artist.
It’s doubly annoying because it’s a fairly good tune but the lyrics suck.
I vote for Janis Ian’s Jesse, sung by Roberta Flack.
For me, it’s a little known song by a now defunct group called “Weddings, Parties Anything”.
"Free Falling": Because it reminds me of the love of my life(or so I thought at the time) .
"Boys of Summer",Too Much Time on My Hands",“More Than a Feeling”: Same reason, different loves of my life.
Dire Straits’(s?) “Romeo and Juliet” always seems so heartbreaking to me, for some reason. Especially the last verse:
I can’t do the talk
Like the talk on the TV
And I can’t do a lovesong
Like the way it’s meant to be
Can’t do anything
But I’d do anything for you
Can’t do anything
'Cept be in love with you.
“If I could change your mind” by Alan Parsons Project
I vote for Marie by Randy Newman.
Never Let Me Go by Katie Webster is the sort of song Sony invented the ‘repeat track’ button for. Drinking recommended.
“Black” by Pearl Jam is pretty damn sad: “I know someday you’ll have a beautiful life, I know you’ll be the star in somebody else’s sky, but why can’t it be mine?”
For me it’s Eternal Flame by the Bangles, mostly because it reminds me of my unrequited high school crush.
Another really sad love song: Love, Me. It makes me cry because of some older relatives that passed away recently, the husband one year after the wife.
Unbreak My Heart by Toni Braxton. The sadness in her voice during that song is palpable. I well up every time.
No love for Morris Albert?
Nah. Me neither.
Everybody Loves a Clown by Garry Lewis and the Playboys always does something to me, though.
Someday You Will be Loved by Deathcab for Cutie. Can’t listen to it without tearing up.
Marie by Townes van Zandt is pretty heartwrenching too.
At Seventeen, by Janis Ian. A girl who wants to be loved, but no one will look at her because she’s plain.
Tennessee Waltz, by Patsy Cline.
Last Kiss