“True Companion” by Marc Cohn would have been the first song at our wedding, but Mrs. Viking can’t listen to it without bawling. At least it’s happy tears.
“No One Knows” by Green Day.
The song itself isn’t very sad, it’s just tied forever to a very sad moment in my life.
Elliott Smith - Between the Bars (listen)
…Suddenly I wake up…from the dream I make up…
Of the girl I’ll never know
In a place I’ll some day go
Angels never fly this low
She’s the girl I’ll never know
Frankie Valli and the Four Seasons.
For my first daughter, who died at the age of 3 weeks.
Not to go all highbrow or anything, but the one piece of music that reliably makes me cry is ‘E lucevan le stelle,’ in Tosca.
“Memory Motel” by The Rolling Stones.
Oh, I could write a book. Perhaps someday I will.
Des’ree’s “Kissing You” can bring a tear lately, but for the life of me I can’t explain exactly why. The lyric is sad, but there’s something beyond the face value of it that chokes me up.
I can’t listen to “Wanderin’” by James Taylor without becoming a big puddle. And “Someone To Watch Over Me” by Frank Sinatra. My brother and I made a video montage of family photos for Christmas one year. That was the music we used for the segment on our mom. She’s not here anymore, and I can’t listen to that song anymore. [sniff]
Would it be an imposition if I post the lyrics of a song that means very much to me? Not that I think you folks have not heard it, but because I would like to share it with you. 
Have Yourself A Merry Little Christmas by Judy Garland (from the movie musical Meet Me In St. Louis). I can’t hear that song without picturing poor little Margaret O’Brien bawling her eyes out.
Many of the songs others have mentioned bring a lump to my throat, but the one that makes me lose it completely, as in I have to leave the room, is In the Arms of theAngels It was popular around the time my son committed suicide. I have to think that he’s happier there.
Ok, I’m blubbering now.
No, it wouldn’t be an imposition, it would be a violation of copyright laws and the rules of the board:
That is, of course, unless you wrote it yourself.
I would have certainly provided appropriate attribution. I guess I’ll just take my song and go home. Considering my song was by the Greatful Dead, who to my knowledge have never filed an action for copyright infringement, and in fact incouraged bootleg recordings, and performed free as often as not, I think you were a little harsh.
You can post a link if the lyrics are online.
Considering she saved you from a potential banning, I’d say she wasn’t the least bit harsh.
And to answer the OP, I’m ashamed to admit it, but that song that what’s-her-face sang for Titanic always tears me up. I deserve to be banned for that, I know.
John Lennon’s “Imagine” is always good for a sniffle or two.
Jeff Buckley’s “Lover You Should Have Come Over” is a good one too.
The one that always gets me is In My Life by the Beatles.
Also the End Of Innocence by Enigma from when I was a Sr in highschool and a good friend of mine was killed in a car accident. But that is because that is what I was listenig to when I found out he died.
Several Vysotsky songs, including About the Clairvoyant Cassandra and The End of the Wolf Hunt.
At This MomentBilly Vera And The Beaters
I’m very bad with remembering who sang what, but I think it was Bobby Goldsboro who did “Honey” – the one about the guy whose wife died and now the tree they planted together has grown so tall and how much he misses her.
Also Cats in the Cradle.
Most of all the last song Jim Croce wrote, which contains the line “Never seems to be enough time to do the things you want to do once you find them…”