Telephone Wire, from Fun Home - the way she's in that position of memory, begging her past self to say anything to her dad that might open him up, even though she, and we, know that that's impossible, because otherwise the show, and the pain, wouldn't exist. I was a mess when I saw this on tour.
Children and Art, from Sunday in the Park - "Isn't she beautiful, there she is, there she is, there she is, there she is...mama is everywhere, he must have loved her so much" is one of the saddest and most beautiful lyric lines ever put into any musical. It says so much about love and time in such a strange way, the emotional and conceptual epiphany always catches me off guard.
The I Love You Song, from 25th Annual - The absolutely devastating desperation knocks me over even when I'm just listening to the album while doing chores. When she spells the word and we hear "that is correct" in a distant echo, and then she and her parents sing the last notes in perfect, imagined, and impossible harmony, my heart aches.
Mostly more contemporary choices that have struck me recently. Some are just incredibly moving not so much “sad.” “Unlikely Lovers” - Falsettos “It’s Quiet Uptown” - Hamilton “She Used to Be Mine” - Waitress “Prayer” - Come From Away “Heartbreaker” - Bright Star
Harriet Craig said: "Supper Time (As Thousands Cheer)
This Nearly Was Mine (South Pacific)
Her Face (Carnival)
There's Always One You Can't Forget (Dance A Little Closer)"
I love This Nearly Was Mine and ironically, the best recording of it I’ve ever heard is Kelli O’Hara’s from her album Always. If you’ve never heard it, download it now! ??
CZJ at opening night party for A Little Night Music, Dec 13, 2009.
"I Miss the Music" from Curtains always catches me, though I'm not sure if it counts, since the reason I cry is more due to the backstory of the song (Kander writing the song follow Ebb's passing), but regardless, it gets to me every time I hear it.
"Left Behind" from Spring Awakening.
"Days and Days" from Fun Home was actually more upsetting to me than "Telephone Wire," though I agree both were heart-wrenching to watch.
"Road to Hell II" from Hadestown
"What Would I Do?" from Falsettos
Though, when I think about it, with the exception of "Left Behind" none of these songs made me cry in theatre. I think these are the saddest, though other songs have moved me much more ("Im Here" from the Color Purple and "Answer Me" from The Band's Visit are recent examples).
qolbinau said: "In Buddy’s Eyes - I can’t think of much sadder than a woman lying through her teeth that she has had a happy marriage for 30 years to the man she actually loves. Almost no one can act this song like Bernadette can, especially the last verse. "
I agree with this completely. Also, Not a Day Goes By, the I Love You song - Spelling Bee, Losing my Mind - Follies, Children and Art and We Do Not Belong Together - Sunday in the Park, Without You - RENT, Another Winter in a Summer Town - Grey Gardens, If I Didn’t Believe in You - L5Y.
Besides the ones already mentioned "Good Thing Going" from MWRA always gets to me:
And while it's going along You take for granted some love Will wear away We took for granted a lot And still I say: It could have kept on growing Instead it just kept on We had a good thing going Going Gone
Another moment that always chills me with its sadness is when Evan Hansen sings in "For Forever":
And I suddenly feel the branch give way I'm on the ground My arm goes numb I look around
Because the sudden change in melody makes you realize what the "fall out of the tree" was.
I agree that "She Used to Be Mine" has already turned into a modern classic torch song. It's in karoake bars. It's become like Adele's "Someone Like You."
And then I have to say the most collectively sad moment I ever experienced in a theater was the final performance of The Great Comet. When Lucas Steele started singing "Goodbye my gypsy lovers" and his voice broke in the middle of the song and I looked around and saw the Imperial Theatre staff wiping away huge sobs and some of the ensemble cast quietly crying.
The title is a clue: "All the Sad Young Men" from "The Nervous Set"...the song is awfully beautiful and heartbreaking. Mabel Mercer sang it and many others subsequently.
“What Would You Do?” from Cabaret “Down” from Grind “Marieke” from Jacques Brel... “There is No Other Way” from Pacific Overtures “Dear Friend” from She Loves Me
The line "Once I was told good men get better with age. We're just gonna skip that stage" destroys me every time. That second act in general is ruthlessly heartbreaking.
poisonivy2 said: "And then I have to say the most collectively sad moment I ever experienced in a theater was the final performance of The Great Comet. When Lucas Steele started singing "Goodbye my gypsy lovers" and his voice broke in the middle of the song and I looked around and saw the Imperial Theatre staff wiping away huge sobs and some of the ensemble cast quietly crying."
THIS. Although I wouldn't qualify any of the songs in that show as the saddest songs, every number that afternoon was tinged with remarkable sadness. That show was the most emotional, beautiful experience I've ever had inside of a theater, alongside over a thousand equally emotional strangers both onstage and off.
You can really see the diversity in age groups in response to this thread. The 'kids' are all about the current shows while us old queens bring up the classics. I will say that the quintessential sad song for me is 'How Could I Ever Know' from The Secret Garden.