It was the final song in the final episode of my favorite show.
Ελευθερια Αρβανιτακη "ΤΖΙΒΑΕΡΙ.
Crash Test Dummies - Supermans Song.
To me it’s about loneliness.
This song isn’t just sad, it’s downright depressing: Roberta Flack’s *Ballad of the Sad Young Men.
*
My current one is by James Bay and it reminds me of all the fights my husband and I used to have. Now, I don’t have any choice but to Let it Go. 
And this one just reminds me of him in general, because it was his favorite song. Now it makes me cry. Thanks, Bob Seger.
It’s probably cliche, but I gotta go with Gary Jules’s version of “Mad World.”
The verse about children waiting for the day they feel good breaks my heart every time.
The saddest song I know is “And the Band Played Waltzing Mathilda,” written by Eric Bogle. My favorite version was sung by Ronny Drew of the Dubliners.
I can’t provide a link now- perhaps someone else can.
Good one, I would say " Traces" by Classics IV
Is it OK if I jump in without having been part of the challenge from the beginning? I don’t care about the money. I just want to contribute to the thread.
Where’d You Go by Fort Minor - song begins at 1:03. It reminds me of the time shortly after my ex and I first split up. I’m friends with him and his folks now, and he comes to see our daughter regularly, but this song still takes me back to when the pain was still raw and my daughter would ask when Daddy was coming back to live with us.
Time In a Bottle - Jim Croce. One of my mom’s favorite songs. She died four years ago this past Sunday, and I still miss her. Now that she’s gone, the lines
But there never seems to be enough time
To do the things you want to do
Once you find them
hit so close to home.
This came out two months after my father died in 1989 and it* still *absolutely wrecks me.
This is five songs: Mahler’s Kindertotenlieder (Songs on the Deaths of Children).
The poetry comes from a group of 428 poems Friedrich Rückert wrote after his children died of Scarlet Fever, which somehow makes the whole thing that much more depressing.
I thought that video was sad, but I liked it. Now that you’ve pointed-out the lyrics… it’s almost unwatchable! I should not have viewed that at the office this morning. 
Here it is, at last.
Blind Willie Johnson - Dark Was the Night, Cold Was the Ground.
I’m late to the party and missed the first 3 days. I don’t care about the $1, but to catch up, here are my first 3 entries:
1 - Favorite song:
Edward Elgar - Nimrod from Enigma Variations
2 - Least favorite song:
Tough one. I don’t listen to stuff I don’t like on purpose. Though, I’ve always despised Spin Doctors - Two Princes.
3 - A song that makes me happy:
Leo Kottke - Snorkel. My main motivation for recently buying a 12-string guitar was to play this song on it.
4 - A song that makes me sad:
Grandaddy - Jed the Humanoid. It’s about a robot that drinks himself to death after his creators move on to other inventions. Jed’s Other Poem is another track on the album written from the robot’s perspective with an awesome music video created on a 1979 Apple II+.
Ok, as another 12 string owner, and a bit of a Kottke fan, I have to ask: How close have you gotten?
Actually pretty close! It’s in open G with alternating thumb bass on the right and a lot of pull offs/hammer ons in the left. The left hand is actually pretty simple. The hardest part has been getting used to fingerpicking a 12 string vs. the classical I usually noodle around on. It also takes some practice to get the muting of the bass notes right to give it the Kottke “oom pah” sound.
This guy shows how it’s done pretty nicely.
Here is the link.
“Unforgettable” by Nat King Cole and Natalie Cole:
Queen- “These Are The Days of Our Lives”
Gotta post both of these - after our parent’s divorce, my mom took up the piano again, and worked on this as a sort of therapy and became (along with Lennon’s “Mother”) the theme for those times. Her late at night playings of it (and Scott Joplin lol) made for an unsettling lullabye, and part of my DNA:
In her last two months of level ten pain, she could at least still hear, and we made sure that the Chopin and other couple other oldies were on the cd player. This period is summed up by this number, which is very difficult for me to listen to now:(song starts at 9:45)
that’s a fine number