Adam’s Song-Blink 182
This song always reminds me of my dear friend Nick who decided, at the age of 17, that his girlfriend cheating meant his life was over and the only way to rectify the situation would be to suck on the busy end of a shotgun.
Dammit Nick 
Goodbye to You by, erm, whoever the heck sings it, tends to make me a little sad, with some resentment sprinkled in. When I was in high school, some of my ‘friends’ decided they wanted to use that as our graduation song, with some of the words changed. It didn’t get used, but now I tend to associate it with high school. I don’t get sad because I miss it–I’m glad to be out of that place–but because I wish high school hadn’t sucked so much for me. (The resentment comes in in that since then I’ve realised that those ‘friends’ were never really my friends at all.) I wish I could have had real friends during those years.
Geek alert: “The Hornburg”, “The Gray Havens”, and “The Breaking of the Fellowship”–from the Lord of the Rings soundtracks–all make me burst into tears. Every single freaking time. Never fails…
“Miserere”, by Allegri, gets me in a good blue funk, and the Last Reveille (the tune they play at the memorial service for the war dead on Remembrance Day) makes me sad in a solemn, dignified sort of way.
When My son died, the song In the Arms of theAngels was popular. I still burst into tears when I hear it. 5 years
Where Were You When the World Stopped Turning by Alan Jackson. That sone came on the radio a few days ago, and after it was over we had to pop in Toby Keith’s Courtesy of the Red White and Blue to pep us up.
Jackson’s song has been read into the Congressional Record.
Pretty much every Aimee Mann song, but especially Just Like Anyone.
“And I will wonder, just like anyone, if there was something else I could have done.”
Drawn to the Deep End by Gene
“Everyone has a place, I know mine. In bed where I was born, where I live, where I’ll die.”
And of course I can always count on Morrisey/The Smiths for depressing dittys like Suffer Little Children. “A woman said I know my son is dead… I’ll never read my hands on his sacred head…”
Ok, time to flip the iPod back to the Cardigans to cheer me up. 
Gordon Lightfoot’s “The Wreck of the Edmund Fitzgerald” - it’s sad because it’s true.
Jewel’s “You Were Meant For Me” - She does a good job of relating crushing emotions. However, it sounds like whoever she broke up with was a jerk.
ELO’s “Big Wheels” - mainly because of the strings.
The Carpenters’ “Superstar” - This applies to nearly anything sung by Karen. Even a song as peppy and uplifting as “Top of the World” sounds a bit darker when she sings. Hard to believe she’s been gone for over 20 years.
‘With a little help from my friends’ - mainly because it was played, slow and sad on a beautifully toned piano, at an ex SO’s funeral,
and 'how ‘bout another first kiss?’ by they might be giants, because this ex-SO sang it to me in an attempt to make amends one of the last nights I saw him. Incidentally the same night he insisted that we should iron everything out because we’d never see each other again.
Tough breaks.
Thanks, nate, big-guy-in-the-sky, for making me cry again…
Oh, and Rainbow Connection, for the same reason as ‘with a little help’. Absolutely can’t hear that song without losing it.
The River by Garth Brooks always makes me think of my Uncle Bob. He loved anything associated with boating. He was also my father figure since my jerk of a dad walked out (probably why Dance With My Father also gets me weepy- I never got to talk or dance with him before he died).
Anyway, he had visited my home on his way to a fishing trip and was going to come back and visit again and play cards with me (a tradition between us) afterwards. He died on the trip. I have always felt like I didn’t get to say goodbye.
I just wanted to second this song.
Listening to a lone bagpipe player in the distance (Amazing Grace) watching the sun go down into the sea.
The ones that do it for me are a couple off Hüsker Dü’s Candy Apple Grey album. I think it’s intensified by the fact that they come one after another. “Too Far Down”, which is about depression, and “Hardly Getting Over It”, which contains these lyrics in the final verse:
“Grandma, she got sick, she is going to die
And grandpa had a seizure, moved into a hotel cell, and died away
Now my parents they just wonder when they both are going to die
And what do I do when they die?”
I also agree with the Elliott Smith selection and “The Rainbow Connection”.
Elliott Smith again, but in particular Pitseleh and Needle In The Hay. Needle In The hay was of course playing as Baumer attempted suicide in The Royal Tenenbaums.
Last Goodbye, Lover You Should’ve Come Over, and Hallelujah, all by Jeff Buckley.
Tell Her by Del Amitri.
Missy Higgins has also been mentioned, but I’ll go further to say anyone here that hasn’t heard her before will do well to check out her album “The Sound Of White”.
And so many more, but these ones immediately spring to mind.
It’s nice to feel sad sometimes.
Well, it was designed to be sad from the outset, but Gortoz a Ran from the Black Hawk Down soundtrack tugs at the ol’ heartstrings.
Damn straight, it does.
Criminy, I think I hate whoever started this thread…
She’s starting to get a fair bit of airtime over here - I caught a concert of hers on one of the music channels and liked the sound of it - how many albums does she have?
I have a CD, the last few tracks of which are David Gray’s This Year’s Loving, Jeff Buckley’sHaleluja, Mad World by Gary Jules, Lux Aeterna and Arms of the Angels. A beautiful run of songs, but one that finished with me in a flood of tears
Songs that make me sad: “Watching Over Me” by Iced Earth; “Theater of Pain (Orchestral Version)” by Blind Guardian; “To France” written by Mike Oldfield as performed by Blind Guardian; “Watcher in the Sky” by Iron Savior; “Dead Meadow” by Black Label Society.