Look guys I don’t cry. But the song that always “gets me right there” is
The Beatles In My Life (good call geogeek) It’s not actually a sad song, more wistful, but it definitely pushs my buttons.
For me, that one is “Be Alone Tonight” by The Rays, from “School Daze.” A few friends in college did a skit singing this and one of them was killed in an accident the following year.
Generally speaking:
“Catch the Wind” by Donovan, so wistful and resigned
Almost any ballad by Stan Rogers, as they’re all beautiful and there won’t be any more.
My “happy tears” one is Collin Raye’s “One Boy, One Girl”. Aaaawww. 
How could I have forgotten “Goodnight Saigon”, for itself and the madness of war in general.
Now I need to leave work early to go home and listen to “Rent”!!
I love By Way Of Sorrow as well. As long as we’re talking Cry Cry Cry, how about Northern Cross?
Old memories have faded
Nearly all of them are lost
Except for your face, shining
'Neath that northern cross
I am also completely shattered by James Taylor’s New Hymn:
*Absolute in flame beyond us
Seed and source of Dark and Day
Maker whom we beg to be
Our mother father comrade mate
Til our few atoms blow to dust
Or form again in wiser lives
Or find your face and hear our name
In your calm voice the end of night
If dark may end
Wellspring gold of Dark and Day
Be here, be now*
Interestingly enough, if you ever hear the original demo versions of this song, it was originally based on the band having used so many recreational drugs that they were no longer having any effect on them (which apparently contributed to their first split). It was only later that the song was reworded to make it about someone dieing and the medicines no longer being able to save them (possibly Ashcroft’s dad).
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The part that kills me is the reprise of “I Don’t Know How to Love Him,” sung by Judas before he hangs himself.
“No One Is Alone” from Into the Woods gets to me, too, as do a few songs that have been mentioned already – “Golden Slumbers,” and some of the Les Mis and Rent stuff. And there was a song we did in choir when I was an undergrad called “Mary Speaks” – it had a lovely text by Madeleine L’Engle – which was just heartbreaking.
If we want to be highfalutin classical: the bit from the end of Britten’s War Requiem, where the tenor and baritone sing “Let us sleep now…” and the choir answers with “In paradisum dedicant te angeli…” kills me dead. Every time.
Actually, a lot of War Requiem does that. That’s why I don’t listen to it very often.
Nothing is sadder than Red Foley’s Old Shep. You can find it right here: http://www.vaxxine.com/steveb/misty/oldshep.eht This is the reason we need a Constitutional Amendment to protect the relationship between a boy and his dog.
I’m not a crier, generally, but songs that give that feeling:
Cat’s in the cradle
Runaway Train by Soul Asylum.
Walkaway Joe by Trisha Yearwood.
Hallelujah by Rufus Wainwright
Damaged, TLC
Very recently, I MIss You by Blink 182.
Probably more so than any of those: Perfect by A Simple Plan.
http://www.metrolyrics.com/lyrics/133373/Simple_Plan/Perfect/
Oh me too. Just thinking about the opening orchestral bit makes me catch my breath.
I agree with “Tears in Heaven”, “Puff the Magic Dragon”, and “This Woman’s Work.” I’ll add…
REM - “Everybody Hurts”
Tim McGraw - “Don’t Take the Girl” - corny, but it gets to me
“I’ll Be Home For Christmas”
“The House At Pooh Corner”
Kate Rusby - “The Unquiet Grave” - the combo of her mournful voice & the lyrics
Nino Rota - “What is a Youth” - From Zeffirelli’s Romeo and Juliet, 1968 - the music is so of surrendering and mournful
blush Moving Pictures - “What About Me”
deeper blush from when I was a kid, Dolly Parton’s “Me and Little Andy.” A little girl shows up on the singer’s doorstep with her dog, Little Andy, asking for a bed for the night. The part that got to me was that the dog dies too.
God knew little Andy
Would be lonesome with her gone
Now Sandy and her puppy dog
Won’t ever be alone.
corny as hell… but I’m tearing up right now.
Try to Remember that kind of September is very hard to listen to post 9/11.
Deep in December it’s nice to remember
Without a hurt, the heart is hollow.
I have two:
“Hurt” as performed by Johnny Cash, especially after seeing the video and how old age had caught up with someone who will always be one of the coolest/baddest men to ever live. (I know it was a cover, but his version is much more powerful to me)
“At Last”, by Etta James. It reminds me of a time when I was involved in a budding relationship with a lady friend that we just couldn’t take any further.
Warren Zevon’s Keep Me In Your Heart
When you get up in the morning and you see that crazy sun
Keep me in your heart for awhile
There’s a train leaving nightly called when all is said and done
Keep me in your heart for awhile
Lots of Warren Zevon songs do it for me, including “The french inhaler” and “Hasten down the wind”
Also “Lorelei” By the Pouges
And almost all the slow songs offDave Alvin’s[ album King of California, especially the title song, “4th of July” and “Every night about this time”
I don’t generally cry at songs, unless I’m listening to them in a depressed mood and for cumulative effect. However, there are some songs that always get to me.
“Hide and Seek” by Howard Jones.
“The Barbara Song” from the Three Penny Opera, especially the lyric-free Gil Evans version.
“Night of the Swallow” by Kate Bush.
“Land” by Patti Smith.
The song cycle from “Society Pages” to “Any Downers” by Frank Zappa.
“Piano Man” by Billy Joel
not because of the song, but because of the memories it’s linked to. I’m a sophomore in high school, and I’ve been involved in 3 school plays. Just before curtain at every show, we gather into the dressing room and sing this song. I’ll never forget the last time I sang it with “the seniors,” whether it’s those who graduated last year, those that will this year, the current juniors, or… when all my friends and I graduate.
Savage Garden’s Truly Madly Deeply, for sentimental reasons.
Billy Joel: Leningrad and Goodnight Saigon… Both just hit me in that spot.
Harry Chapin: Cat in the Cradle. Like a baby, man, like a baby.
I’m no country fan but;
Tim McGraw’s Don’t Take the Girl has me in tears every single time dammit.
And I’ll never forget the day I was driving down the road, listening to the radio, and a song that I had heard many, many times before (with no significant emotional impact) came on. It was Collin Raye’s “I Think About You” ( I believe that’s the title?).
Zooming down the highway, and I suddenly burst into tears. I was nearly inconsolable. To this day I have no idea why it hit me that way, but the song hasn’t had that effect on me again.
Oh and his “One Boy, One Girl” also gets me teary, but in a nice way.
I left off the most notorious one on my list.
Teddy Bear, by Red Sovine.
By the time it gets to:
I’m just wasted. What’s great though is it brings my big, grizzly, gruff dad to pieces too 
Wow, glad to see I’m not alone on Puff the Magic Dragon. That’s probably the one song I can never get through without crying.
- Wind Beneath my Wings* and I Think it’s Gonna Rain Today both by Bette Midler.
Over the Rainbow mostly because of sentimental value.
Oh yes, Into the West by Annie Lennox has been getting the waterworks going lately, mostly because of recently having to put down the family cat(had him for 14 years). 
I’ll have to second Seven Spanish Angels, Wish You Were Here, and Lover, You Should Have Come Over.
I’ll add;
Winter, by Tori Amos
from Little Earthquakes
About a girl’s love for her father. The part right after the crecendo kills me, I get teary during the crecendo…
"Hair is grey and the fires are burning
so many dreams on the shelf
you say ‘I wanted you to be proud of me’
I always wanted that myself
He says ‘When you gonna make up your mind?
When you gonna love you as much as I do?
When you gonna make up your mind?
Cause things are gonna change so fast
all the white horses have gone ahead’
I tell you that I’ll always want you near
you say that ‘Things change, my dear.’"
Europa, by Santana
That man’s guitar is heartwrenchingly beautiful.
Crawlin Back To You by Tom Petty
from Wildflowers
“I’m so tired of bein’ tired
sure as night will follow day
most things I worry 'bout
never happen anyway”
The Dreaming Tree by Dave Matthews Band
from Before These Crowded Streets
“Standing here, the old man said to me
‘long before these crowded streets, there stood my dreaming tree’
…
Mommy come quick, the dreaming tree has died
I can’t find my way home
there is no place to hide
…
Oh, if I had the strength to
I would leave you up
to your own devices
will you not talk?
can you take pity?
I don’t ask much
but won’t you speak, please?”
And when Van Morrison did Comfortably Numb with Pink Floyd…amazing.
Sorry this is very long. I also took the lyrics right out of my head, so I may have a few words wrong.