I, like Abby_Emma_Sasha, can let the hymns get to me…but in pop songs, subtle can’t get me weepy, I need to be hit over the head. The one with the biggest hammer would be One Sweet Day by Mariah and Boyz II Men. Total gospelly melismafest (especially the [url=http://www.youtube.com/watch?v=xNzijLaKqhc] live version at the Grammies in '96). Played at so many funerals…
Have you heard the Sarah McLachlan version? It’s awesome. here it is–someone made their own music video to it, but you can still hear the song just fine if you minimize the video 
Another hand up for Kermit’s Rainbow Connection. I remember hearing the news of Jim Henson’s death on the radio as I drove home and they played that song and I bawled all the way home.
Come Come Ye Saints (perhaps done a million times by the Mormon Tabernacle Choir). The backstory of the people crossing the plains amid much suffering, hardship and death is weepy enough, but the song is also so hopeful and uplifting. That one brings out sad tears and happy tears. I love it.
Another one.
Paul Brady - The Island (Youtube)
Especially the lines
"And I guess these young boys dying in the ditches,
Is just what being free is all about,
And how this twisted wreckage down on main street,
Will bring us all together in the end "
Oh hell, I just remembered another: “Forever Young” as sung by Rod Stewart.
If I ever have kids, I’ll never be able to listen to that song without falling apart for days.
That was my graduation song. For many years I couldn’t listen to it without tearing up. Damn, my 20-year reunion is next year. Now I feel old…
I just remembered another song that made me cry. “Where’d You Go” by Fort Minor. It came out around the time my ex and I first split up. Eventually he moved back in for a few more months, but that song still made me cry.
There are a number of country songs, but the current one that makes me tear up like a little girl is Jamey Johnson’s “In Color”, where the narrator talks to his grandfather about a cache of photos and their subjects:
"I said, Grandpa what’s this picture here
It’s all black and white and ain’t real clear
Is that you there, he said, yeah I was eleven
Times were tough back in thirty-five
That’s me and Uncle Joe just tryin’ to survive
A cotton farm in the Great Depression
And if it looks like we were scared to death
Like a couple of kids just trying to save each other
You should have seen it in color."
Also, “I Will Buy You a New Life” by Everclear:
“I hate those people who love to tell you
Money is the root of all that kills
They have never been poor, they have never
Known the joys of welfare christmas.”
“Will The Circle Be Unbroken” also makes me cry, because of the following lyrics about a mother:
“Undertaker, undertaker, undertaker please drive slow
For that woman, that you’re carrying, Lord I hate to see her go.”
And finally, “If We Make it Through December” by Merle Haggard. You can look up the lyrics on your own, even reading them will make me weepy. I read somewhere it is one of John McCain’s favorite songs, and I would rather put a rusty nail through my eye than tear up again at hearing it.
Operator by Jim Croce gets me every time in the middle of the 2nd verse.
Also the video for Johnny Cash’s Hurt really chokes me up.
That one Christmas song about the little boy buying shoes for his ailing mother gets me every. freaking. time.
Aside from that…
Life by the Drop, by Stevie Ray Vaughan
Castles Made of Sand, by Jimi Hendrix
Green Fields of France (cover), by Dropkick Murphys
Faraway Boys, by Flogging Molly
and
I Can’t Make You Love Me, by Bonnie Raitt.
I’m getting a little misty just thinking about 'em, really.
Just a Housewife from the musical Working Ugh. It got to me when I was younger and heard it. Even worse after I had kids and started staying at home to take care of them. Oy.
On the fathers and sons subject, there is a great song called “Don’t Lose Me Boy” by The Bacon Brothers. Also another by them called “Brown Eyes” that is about Kevin’s kids and wife. And come to think of it, another called “Chop Wood” about legacies of love and respect (or lack thereof).
I could go on, but I think I’ll just go pull up some mp3s and weep instead.
I first heard this one on the tail end of an episode of “House.” I cried so hard, I had to go look it up and find it. Naturally, I didn’t download it illegally or anything. Then to read Jeff Buckley’s rather tragic, cut-short life. What a waste of beauty.
“I Am Trying To Break Your Heart” by WILCO gets me every goddamned time. It captures the feeling of the wheels falling off your life so perfectly. I can’t stand how it makes me feel, but I will listen to it and sing along every time it goes by…
Sandy Denny - Take away the load (lyrics)
Gets me every time, as do a few other songs by her. It is a combination of the sentiment and the thought that she died too soon.
Maybe the studio release is better? Because I’d never heard of it and so I went to find it and all I found were live performances on YouTube, and they were horrible*–bored to tears after 30 seconds and didn’t make it to the end of any of them–I tried three different ones. The lyrics don’t have much impact on their own so I can only assume it’s something about the delivery in the album version?
Here is another one for me… maybe 50% of the time when I try to sing “Christmas Dinner” by Peter, Paul, and Mary I can get all the way through without crying. Ok maybe more like 40%.
*edited to add: this is often the case, I find. I virtually never like recordings of live performances.
Edited again to add: I found a non-live recording of the song I myself listed: here
I love Elton John’s “Sacrifice.” He doesn’t perform it much, but I had the honor of hearing him play it at a benefit concert for Matthew Shepard. Sinead O’Connor also does a painfully beautiful cover.
The second movement of Dvorak’s New World Symphony also gives me a lump in my throat every time I hear it.
I was just listening to a mix tape that someone made me back in college. Man… Eye of the Hurricane still packs a punch!
Have you ever heard it on the pipes? The tune from the 2nd Movement was used as the basis for the spiritual “Going Home”, which then jumped to the pipes.
It’s often played at funerals, the most notably being the funeral of the golfer Payne Stewart. There was a heavy mist, and the piper walked away from the service into the mist, playing Going Home, and leaving only his footprints in the dew.
That was definitely lump-worthy.
If we’re talking embarrassing, then I have to add Our Town by James Taylor (the one from the movie Cars).
Me too. It makes me think of my brother and my grandmother. She used to sing that to him when we were little. They played it at her funeral and I cried for the both of them. Takes me back to that day everytime I hear it.
I hope you dance by Lee Ann Womack makes me tear up everytime. It makes me think of my children and the lives they have yet to lead and I hope they dance through life with the least amount of cares.
Daniel by Elton John is another one.
“Daniel my brother you are older than me
Do you still feel the pain of the scars that won’t heal
Your eyes have died but you see more than I
Daniel you’re a star in the face of the sky”
My brother took his own life at 18 and that part of the song turns me into a blubbering idiot everytime.
sob
It’s if you get there, before I do (don’t give up on me… i’ll see you when my time is through…" Ick. While it’s a beautiful ballad, and a crafty piece of work - it came out right about the same time my mum died… and I nearly killed myself everytime I heard it while driving on the expressway… Sheesh !