When I Fall by Barenaked Ladies can make me cry. Why Does My Heart Feel So Bad? by Moby as well, though they are two of my favourite songs.
Last Kiss, the original, used to because it was my lullabye sung by my dad when I was little. Always made me sad.
Another one, though I don’t hear it too often, is the song the Spud sings after Tommy dies in Trainspotting. You know, “Do you think I would leave you crying, when there’s room on my horse for two?” I don’t know where it comes from or who it’s originally by, but I find myself singing it, and I get a little misty eyed.
My number one misty-eyed song is Friends by the Hawaiian group Na Leo Pilimehana. It’s about unconditional friendship and separation and it’s a guaranteed tear-jerker around graduation time in Hawaii, let me tell ya.
And, based on my own long-distance relationship problems, both Say You’ll Stay by Kai(?) and I Don’t Want to Miss a Thing make me blink tears back real fast, lest I resemble a blubbering fool (any more so than usual)…
“With Pen in Hand”–Vikki Carr. I think she almost cries near the end.
“Tucumcari”–Jimmie Rodgers
“Last Farewell”–Roger Whittaker
“500 Miles Away from Home”–artist unknown. Our family used to joke about this song in the 60s; we pictured a traveler going in a circle and always being “500 miles away from home.” In recent years I saw the sheet music; the lyrics told about someone who really missed his family–and I didn’t laugh about it anymore.
How about Pink Floyd, “When the Tiger Broke Free”. Wow!
I also discovered (today at work when I heard it on our Musak system). “You’ve Got a Friend In Me” from the Toy Story movies. My closest friend (more like a mom) moved away in Feb, and we saw both movies together. I heard it today and went instantly into tears. Talk about unexpected!
Living in Shame-the Supremes. If this one don’t tear ya up, I could crack an egg on yer heart if ya had one, man. Center of Your Will-Twyla Paris. Where You Are-Gypsy Soul. Talk to Me-Gypsy Soul. I Will Always Love You-Dolly Parton, fer crissakes, not Whitney!
…I had to actually pull off the road when I heard this one.
Gram Parsons and Emmylou Harris - In My Hour of Darkness - there’s three verses about different people fading away/dying, with an amazing chorus about trying to find the strength to put up with knowing about all the things that go wrong in people’s lives.
*My Hero - Foo Fighters. Not super sad.
*Wonderful - Everclear. My parents aren’t divorced, but if they were, this would make me more sad.
*Layla - Derek and the Dominoes.
*Hey Jude - Beatles.
When Toy Story 2 was first released, someone here said she “almost” cried during “When She Loved Me” by Sarah MacLaughlan. Almost? When she sang it on the Oscar broadcast, I had to hold my Cartman doll very tight and think about all the horrible things he’s done and said so I wouldn’t lose it. (I let Cartman stay up to see if South Park would win best song.)
Do you know that song is about stalking?