I'll also throw a strange one in the mix. It's not necessarily "sad" but Where Did the Rock Go from School of Rock always makes me think about several passions of mine that I am unable to live out due to the demands of adult life.
I’ll echo a lot of what’s been mentioned. It’s Quiet Uptown, Days and Days, Telephone Wire, Your Daddy’s Son, Bill, Send in the Clowns, Go Back Home, and I Dreamed a Dream.
A few others:
Back to Before from Ragtime
You’ll Never Walk Alone from Carousel.
And the ultimate gut-punch of a song — I’ll Be Here from Ordinary Days.
-Something's Missing (Come From Away) - I think that's at the top of the list for me... If you want to cry continually for 5 and a half minutes, that's the way.
-Ti Moune (Once On This Island)
-A Part Of Us - Once On This Island
-Children and Art (Sunday In the Park With George)
-Your Daddy's Son (Ragtime)
-I Dreamed A Dream (Les Mis)
-Higher (Allegiance)
-I'd Give My Life For You - Miss Saigon
and so many more...
you found your heart but left a part of you behind <3
I am going to add "Just Like That" from "A Christmas Story". I love how it starts off as the mother trying to get Ralphie to stop crying by reminding him that these bad times are over "Just Like That", but the song's meaning changes into the mother's lament that her children are growing up so quickly and she wishes they could stay just the way they are; that their childhood will be over "Just Like That". A sentiment most parents can identify with.
IMO Les Mis corners the market here, between Eponine's On My Own and Fantine's I Dreamed a Dream.and Empty Chairs at Empty Tables, as well as Valjean's Bring Him Home. In addition...
-- What Would You Do? from Cabaret is heartbreaking, particularly when sung by Lotte Lenya
-- All I ask of You from Phantom, specifically as sung by the Phantom at the end of the show;
-- To me, Move On is very sad in the context of the show; young George is at the end of his rope; all I could think of was how alone he was at that point, and the song is so haunting.
-- Rose'sTurn. It may be bravura, but it is very sad. At that point, she is questioning her whole life.
-- Not While I'm Around, in the context of the show.
-- When Your Feet Don't Touch the Ground from Finding Neverland.
-- Make Them Hear You from Ragtime
-- This Nearly Was Mine from South Pacific
-- I've Grown Accustomed to Her Face from MFL
-- The Party's Over from Bells Are Ringing
-- I Never Loved You from Cyrano
-- Once Upon a Time from All American
-- Send in the Clowns from ALNM
-- If He Walked Into My Life Today
-- Some Other Day from On The Town
-- The Impossible Dream, specifically in the finale
-- Far From the Home I Love and Anatevka from Fiddler
-- Something Wonderful from TKAI (it is a beautiful song, and always makes me sad when it is well done)
-- For Good From Wicked
-- Stay Alive and Who Lives, Who Dies, Who TellsYour Story from Hamilton
Agree with posters re You'll Never Walk Alone, Tell Me It's Not True, Words Fail, I'd Give My Life For You, Welcome Home, I Won't Send Roses.
The Chavaleh Ballet from Fiddler on the Roof moves me to tears every time without fail. The last 20-30 minutes of that show absolutely wreck me in the best way.
I think some people are confusing sad songs with songs that make them cry. For instance, I don't see Back to Before from Ragtime to be sad, but I cry when I hear it. I actually think it to be somewhat joyous song that closes the arc for Mother - she has finally become a full person standing on her own as a result of her experiences and is not the china doll that she was before.