There are a bunch of sad moments in musicals, although I suppose it’s the show, not the song, that really makes me cry. Among them:
-The tributes to Angel, and the finale, in Rent
-The death of Fantine, and the finale, in Les Miz
-The monologue (I think the character’s name is Paul) about the drag show in A Chorus Line
and perhaps most of all
-The brave and glorious but doomed finale, in Porgy and Bess
Mostly mentioned already, two of Sarah McLachlan’s songs: I Will Remember You and Angel, Eric Clapton’s Tears in Heaven, and Judy Garland’s *Have Yourself a Merry Little Christmas *. These make me cry because of the deaths of loved ones.
For as long as I can remember, many WWI and WWII era songs such as Vera Lynn’s We’ll Meet Again have made me cry.
And then there’s the previously mentioned culprit Puff the Magic Dragon…gah…I always try to stop listening by the time it gets to “A dragon lives forever, but not so little boys…”
Don’t you forget about me- Simple Minds
Whenever I hear it, I think of that Futurama episode where Fry thinks his brother stole his 7 leaf clover. They play this song as the camera pans out at the end of the episode. That ep always makes me cry, and by extension the song too.
Futurama also ruined Connie Francis’ I Will Wait for You for me. 
:…(
::Sniff::…SEYMOUR LIVES!
“Case of You” has to be one of the richest, greatest songs ever written. The mixing of the art, the liquor, and the sexual images has never been deeper or more playful.
“Catch the Wind” by Donovan is a great “late night driving around and feeling sorry for self” song
Personal association, I get chocked up every time I hear or sing “Be Thou My Vision,” both funeral connection and I remember singing it right after 9/11…the line “thou my high tower” I think the entire choir went to pieces.
:::points and laughs:::
oh wait.
I cried at this too… :o
Her Song for Sharon gets to me, especially this:
<snip>
A woman I knew just drowned herself
The well was deep and muddy…
…my friends were calling up all day yesterday
All emotions and abstractions
It seems we all live so close to that line
And so far from satisfaction"
<snip>
and
“you still have your music
And I’ve still got my eyes on the land and the sky
You sing for your friends and your family
I’ll walk green pastures by and by”
Ramshackle, by Beck. Late at night, with the lights dim.
“Whisperin’ Pines” by Johnny Horton, mostly because it reminds me of my friend and former boyfriend who passed away at 34.
“When I Call Out Your Name” which was played at my baptism. Gets me every time.
Just for the record, I can’t stand “Tears In Heaven”. I’ve lost a child too, but I sure wouldn’t try to make money off it! Sure, write the song, play it at midnight by yourself, but don’t sell it! Tacky, tacky, tacky.
What didn’t I put in enough smilies to make it clear I was just funnin?
Back to the topic:
Jose Luis Perales sang a song called Y Como Es El, a beautiful song about a man letting his cheating lover go, with love and compassion and sadness without any bitterness. Never fails to bring a tear.
Something. I just watched THe Concert for George this weekend, and near the end, Paul starts playing Something on the Ukelele, and he sings about a verse of it, and then the other musicans start playing quietly, and then the music swells and then Clapton started singing with Paul and then I started bawling and now I can’t listen to the song without getting all emotional.
I’m Not in Love by 10cc
I was a heartbroken teenager when that song got airplay.
My short list:
**Tears of Rage ** - The Band
**Holy Mother ** - *Eric Clapton * - written in memory of Richard Manuel, member of The Band (and incidentally, the guy who sings “Tears of Rage”) after he killed himself - heartwrenching song, really!
Songbird - Fleetwood Mac, although Eva Cassidy’s version is almost sadder
**Let It Be Me ** - Everly Brothers
**Starry Night ** - Don McLean
Operator (That’s Not the Way It Feels) - Jim Croce
**Tennessee Waltz ** - various artists, most recently Norah Jones
**Oh, Girl ** - The Chi-Lites
**Let Me Know ** - Robert Cray
**Helplessly Hoping ** - CSN&Y
**Someday Never Comes ** - CCR (since we’re on the initials 
)
**A Song For You ** - *Leon Russell * (then covered by Ray Charles, but Leon’s version is actually more “emotional” - his voice is so darn cool!)
MLS, The Jim Croce song you were looking for is called Time in a Bottle, and it definitely gets my vote as well.
Logan.
Some that have always gotten me. Even more so lately, given recent heartache…
New #1, Bob Mould:
Sometimes I try too hard to separate the
Good times from sadness that we’ve had together
Balancing, I need to keep it all in some perspective
Calm me down, I need you more than you will ever comprehend
I don’t want this to end / I can’t lose one more friend
I go through my regrets and I return the compliments and
Hope I find that innocence, I’ve got to be here no matter what happens
Willing To Wait, Sebadoh:
but oh, when i saw you again
a beautiful friend, she opened up her heart and let me in
no, i cannot lie to you
i’m still in love with you
and i only wanna be with you
Pictures Of You, The Cure:
If only I’d thought of the right words
I could have held on to your heart
If only I’d thought of the right words
I wouldn’t be breaking apart
All my pictures of you
Looking so long at these pictures of you
But I never hold on to your heart
Looking so long for the words to be true
But always just breaking apart
My pictures of you
Another Song About The Rain, Cracker:
Gotta knife straight from my heart
Another time went to you
Another place where we were smart
Before the flood and time was through
I sing myself to sleep at night
I sing myself to sleep
Another song about the rain
Coming down it burns through me
Another song about the rain
Trouble, Coldplay:
Oh no, I see
The spider web is tangled up with me
And I lost my head
And thought of all the stupid things I’d said
Oh no, what’s this?
A spider web and I’m caught in the middle
So I turn to run
And thought of all the stupid things I’d done
Come Talk To Me, Peter Gabriel:
Won’t you please talk to me
If you’d just talk to me
Unblock this misery
If you’d only talk to me
Don’t you ever change your mind
Now your future’s so defined
And you act so deaf so blind
Come on, come talk to me
Come talk to me, come talk to me
I can imagine the moment
Breaking out through the silence
All the things that we both might say
And the heart it will not be denied
'Til we’re both on the same damn side
All the barriers blown away
Mercy, Mojave3:
your life is like a song, you’re living like a fool
you’re living like a fool, but i can’t tell you right
you’re taking all the time, you’re taking all my time
you’re living like a fool, and i can’t tell you right
mercy i can’t see your heart
i can’t feel your love
mercy i can’t see your heart
i can’t feel your love
For those who don’t know these songs, I wish there was some was some way better than listing lyrics to convey the emotion in them. I can only recommend that you try finding them someplace and giving them a listen if you haven’t heard them before.
Sorry if this post is a bit long.
For me it’s “Signore, Ascolta!” from Turandot, “Un Bel Di Vedremo” from Madama Butterfly, and “O Mio Babbino Caro” from Gianni Schicchi. Is it obvious that I’m a Puccini fan?
I can rarely make it through Roger Waters’ “Watching TV” without tearing up. I might be able to handle the song in and of itself, but as soon as it gets to the sound clip of the sobbing Tiananmen Square Massacre survivor saying “Long live the Republic!”, I lose it. And I don’t even speak Chinese.
“Anthem” from Chess, lyrics by Tim Rice, music by Bjorn Ulvaeus and Benny Andersson:
No man, no madness, though their sad powers may prevail
Can possess, conquer my country’s heart, they rise to fail.
http://www.abba-world.net/songs/lyrics/anthem.htm
Tommy Korberg’s version from the Original Cast Album is amazing.
Streets of Heaven by Sherrie Austin
That’s the newest one that brings tears to my eyes, but a whole lot of the other ones mentioned have in the past.
Ive got 2.
Tell Me There’s a Heaven by Chris Rea off of the Road to Hell album always gets me a bit misty, and I’m Not Feeling It Anymore by Van Morrison off of Hymns To The Silence. That one kind of wells it up in me for no discernable reason. Both great songs tho.