“Four Strong Winds” (the Neil Young and Johnny Cash versions). I only started paying attention to this song recently, but once I did, boyohboy. I always get a little choked up. I don’t know why. I’ve never been to Alberta. I haven’t suffered too greatly in the life the way the narrator has. Why it hits me so hard (other than it just being a great song) I don’t know.
What songs do this to you?
Hollow - Godsmack
I Love You - Sarah McLachlan
The Bonny Light Horseman - Cherish the Ladies
Those are the only 2 off the top of my head
The Rare Auld Times – version by Flogging Molly.
– Never been to Dublin
– I’m not too much nostalgic for any city.
– Neither too nostalgic for old tradesmen.
But I guess any poignant Irish music makes me a bit weepy. I think the singing style of weepy Irish ballads influenced power pop/new wave whiny songs and through that emo.
Damn you, uncle squeegee. I just got choked up thinking about “Four Strong Winds.”
I have a King’s Singers CD of British folk songs, and their arrangement of “Down by the Sally Gardens” also does it for me.
Damn. “Four Strong Winds” is one difficult song to sing along to and not get choked up, and you’re right: for what reason?
I know a lot of songs that do choke me up, but the reason is apparent.
The only other one that I can think of that fits the OP is “Hallelujah” by Leonard Cohen.
Both songs written by Canadians. Maybe there’s a trend…
John Stewart’s “Mother Country,” and I’ve been listening to it for 35 years or so.
Moving thread from IMHO to Cafe Society.
Another vote for “Hallelujah.” Also “Eli the Barrow Boy” by the Decemberists, even though I don’t know anyone who dresses in corduroy and pushes a wheelbarrow for a living.
Fields of Gold - Eva Cassidy or Sting (I prefer the Sting cover, myself. Perfect song when you just need a good cry.)
“Russians” by Sting. Maybe it’s a downbeat song, but I don’t know why it makes me just as sad as it does. I think I was influenced by the video
A Change Gone’ Come by Sam Cooke is very moving.
And yet, I was not born by the river in a little tent, nor have I faced racism.
“Solitude” by VNV Nation. It’s not really a slow song, it’s got a bit of a dance beat. It’s a remix of a song called “Solitary”, which doesn’t sound sad to me, and shares most of the lyrics. But that version just has a string line and vocal delivery that sounds sad to me. Clips of both tracks are available here (see the “Signals Edit” version of Solitary as a decent representation of that song).
erg… I just realized I had a lapse in my ability to count. That would be 3 songs…
There are several Irish ballads that will make me choke up… Where are You Tonight (I Wonder) is one in particular.
Sting’s version is the original, not a cover.
I usually know why a song makes me cry (Sting’s Fragile, Pogues’ Band Played Waltzing Matilda cover, many others), but I have no clue why Fleetwood Mac’s* Go Your Own Way* makes me a little sad - lyrically, there’s no reason.
Almost every kinda slow blues-y tune with a bit of a twang makes me somewhat sad, regardless of lyrical content. There’s just something about such music that always makes me think of wasted lives and unfulfilled dreams.
“Always on my Mind” No Matter who sings it
What Mr Dibble said about “Waltzing Matilda”
Even the Pet Shop Boys? 
Chevy Van - Sammy Johns
No clue as to why.
Mother Nature’s Son by the Beatles
Yellow by Coldplay
Desolation Row by Robert Allen Zimmerman.
The first two were the first songs I heard after particularly sad times - leaving a group of friends and knowing I’d never see them again in one case, and learning about the suicide of a friend in the other.
Desolation Row? Who knows.
‘Hello in there’ John Prine
‘Angel’ Sarah McLachlan
We in the UK didn’t get exposed to this with the SPCA advert, in fact not many folk here know it, so we aren’t overexposed.
‘A rainy night in Georgia’ Brook Benton
‘Who Knows where the time goes’ Sandy Denny
‘Hurt’ - Johnny Cash
You can argue about the Nine Inch Nails original version, but its clear both vocalists had their own life experiences to draw on.