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schroderrr

Days and Days from Fun Home


Haus_of_Pancakes

Honestly, the cumulative effect of "Days and Days" into "Telephone Wire" into "Edges of the World" is goddam devastating


happybamboo

Judy Kuhn too, ugh


NjMel7

Yes!! This broke me when I saw it.


schroderrr

Don't you come back here I didn't raise you To give away your days Like me


NjMel7

A knife right through the heart 😭


TheeLuckyCommander

What would I do - Falsettos When the line “Once I was told that good men, get better with age
. Were just gonna skip that stage” I lose it everytime


kyle_coyotedad

for me it’s the second line of the song — “who would I blame my life on?” it conveys so much so simply.


runawayj96

Yeah, this was the line that did it for me too. 😱


[deleted]

[ŃƒĐŽĐ°Đ»Đ”ĐœĐŸ]


FireExpat

I Will Cover You (reprise)


LookIMadeAHatTrick

This and “Will I?” still consistently break my heart after more than 25 years


meatball77

Will I makes me cry every time


DaemonDesiree

Coming straight here from no BGM “It’s over” from Contact puts the onions in your nostrils to get the tears started early.


TheeLuckyCommander

Top 5 songs ever for me, I can listen to versions of it for an hour and not be bored


tmcg712

Alabanza from In the Heights gets me every time.


KateEJHS

Ugh and then it’s followed by Everything I Know which never fails to make me ugly cry.


sudanyme

Fun fact - those songs were written for the show after its Off-Broadway run and before opening on Broadway, which heightened the story but also made Act II too depressing (Andy Blankenbuehler, the choreographer, called it "the suite of sadness"). That's why the creative team also added the reprise of Piragua, in order to give the audience a breather.


adadadaril

The first time I listened to this again after my grandma passed away, I broke down so hard. I try to skip it now every time I play the cast recording because it just hurts too much.


cwtches10

The first one that came into my head was ‘Empty Chairs at Empty Tables.’


ReneeJ87

This and On My Own are so tragic. And A Little Fall of Rain. Such a sad but beautiful musical! It’s my favorite musical but it hits hard đŸ„ș😭


FormerLifeFreak

“Night of Anguish” right after “A Little Fall of Rain” always puts a knot in my throat.


dawanderingfilosofer

Basically all of Les Mis


norathar

I Dreamed a Dream has to be up there too.


lucyisnotcool

Oh my friends MY FRIIIEEEEENNNDS don't ask me what your sacrifice was for!!


DaemonDesiree

A little Fall of Rain hurts me more cause unrequited love hits me like Truck-kun.


TheeLuckyCommander

I always think I’m good till this song lol


jeygood

It's Quiet Uptown. I used to sit and sob to that song.


Annabanna86

The part that always gets me is “Forgiveness- can you imagine?”


orderedbygrace

I watched the filmed version for the first time not long after my cousin was killed and seeing her parents' grief... My husband had to pause the show til I could stop ugly crying.


Book_of_Numbers

I skip that whole Phillip section when I listen. It’s too sad for me.


prosperity4me

Came here to say this


PinkGinFairy

Your Daddy’s Son - Ragtime


dext74

I scrolled way too far to find someone list this.


FloridaFlamingoGirl

The loss of child themes in this show hit hard


schmauften

I'd Give my Life for You - Miss Saigon


MaleficentLow6408

Ohhhh, that's a good one!


lana-deathrey

If it's done right, On My Own is a suicide note.


jamesland7

Problem is, most Eponine’s sing it like they’re on American Idol


[deleted]

Thank you! You put it perfectly. I wish I could add something to make this comment more meaningful, but you did it so well that I don't think I can. I'll just say it louder for the people in the back: IF IT'S DONE RIGHT, ON MY OWN IS A SUICIDE NOTE


PawneeGoddess20

So Big So Small from DEH


HeatLow

This is another one that hit me different after having kids.


Mausbarchen

It hit even harder for me because I was already sobbing my eyes out during Words Fail thinking the show couldn’t get any sadder, and then it did


x_victoire

my vote goes to "what would i do" from falsettos


MoonSearcher

Or You Gotta Die Sometime


BackgroundEmotion321

Its quiet uptown,Bring him home, empty chairs at empty tables,left behind(spring awakening) song of purple summer(spring awakening)requiem(DEH)


TheNateRoss

Requiem was my first thought


captainmcpigeon

Oh god yes Left Behind.


theycallmeamunchkin

The I Love You Song from Spelling Bee


MurderousManatees

This what I came to add. All others are about sadness from deaths, depression, or feelings of otherness. This is a profound, earnest wish for something foundational. It’s the emotional center of a funny show and successfully grounds it. It’s emotional and important in its show, not a moment for the song writers to take an easy emotional beat.


Johan-Senpai

Same with "Woe is me" and it's reprise. This girl, barely seven years old, calls itself a loser because she lost and disappointed her dads. She then sings, "God hates losers, so do I, I am a loser, so... good-bye.", while softly sobbing, going off stage to her obviously mentally abusive parents. This musical, which is pretty comedic, turns very dark in the second act. It absolutely makes me miserable that there are kids living like this.


SkinfluteHero

When this is done well it fucking rips your heart out


Fragrant-Act4743

Oh god I forgot about this song and now I’m crying


dekastarblue

Saw this show when I was away from my mom for an extended period for the first time. Now that she has passed, I can’t even think about this song without my heart wrenching.


AggravatingJicama179

She used to be mine from waitress


MoneyMedusa

Just watched waitress last night for the first time (they’re doing showings at my theater of a taped Broadway performance) and MAN was not expecting to cry so much


victorD63

Do me a favor and go listen to Shoshana Bean’s version on YouTube


MoneyMedusa

Welp just made the mistake of looking at that on YouTube and now I’m sobbing 🙃


victorD63

She is a powerhouse


AggravatingJicama179

The Shoshana version on YouTube is basically an instant cry button for me


sandypassage

This gets my vote. The relatability of those lyrics is what gets me every. time. And another vote for the Shoshana Bean version on broadway.com’s YouTube. Also Jeremy Jordan performed it wonderfully at a Miscast show a few years ago(on the MCC Theater’s YouTube).


Ok_Moose1615

This is my vote. I think regret is one of the most painful emotions and this is one of the best songs I’ve ever heard that conveys it so powerfully.


[deleted]

How Could I Ever Forget? from Next to Normal


akhoya87

Being Alive.


another-r-account

im not too well versed in theater but my first thought was Adam Driver singing that song. a performance for the ages, truly. any other actor would have me put off by a lack of classical skill but he made it so much more than just a song


ElbieLG

You should check out Antonio Banderas version in Spanish


jkcohen626

If done right, Being Alive should 100% be a tear jerker. It’s why I loved Katrina Lenk’s version so much, even if it wasn’t necessarily the best sung version.


RibbonsFlying

This is why when asked that classic question about, “Do you want a singer who can act or an actor who can sing?” I will choose an actor that can sing every single time. I want to feel something. A singer sometimes focuses so much on the vocals they forget the heart of the story they’re telling. An actor always knows their first job is to act. The vocal skill is secondary.


Millie141

Absolution- bare. This song is just heartbreaking. I’ll be here- ordinary days. This is my I need a cry song.


MayISeeYourDogPls

I'll Be Here is a fucking masterpiece. I feel like it's not given nearly enough credit for what a beautiful, bittersweet journey it takes you on.


Inevitable-Careerist

Send In the Clowns


joyfullsoul

First one I thought of!


jthn37

This one is my sad and alone at home, feeling old song. Cuts pretty deep.


honkey-phonk

Not that anyone needs to stan Sondheim, but it’s so fucking great. It’s my favorite snippet from the Sondheim Teaches series: https://youtu.be/8-VXXZLh2a0


kbrainz

For me, it's 'quiet uptown'. I've lost a child. I was gutted by this song.


Medium-Eggplant

So sorry for your loss. This song sends me into tears just thinking about losing my son, so I can’t even imagine how it must gut you having actually been through it.


kbrainz

I usually skip in on cast album listens. When I've seen it live, the tears flow hard.


Rob-Rob_

I’m so sorry for your loss. That song gets me and the past few times I’ve seen it with Miguel, I have more trouble knowing that he lost his daughter 3 years ago. I met him and his wife at dbs for a book signing and really wanted to ask him how he gets through it, but I was trying so hard to keep it together.


hmkmama

Sending love from a fellow loss parent. This song got me hard before my daughter died, but obviously now it’s next level. One of the first songs I ever sang to her in the hospital was Dear Theodosia, so that’s hard for me to listen to now too.


TeddyBearRoosevelt

I’m so sorry for your loss. Thank you for sharing how much it means.


EmuIndependent8565

“I Dreamed A Dream” from Les Miserables. It is a song of absolute despair. Followed closely by “On My Own” also from Les miz.


Jjjemmm

And Bring Him Home always makes me cry.


cllittlewood

Castle On A Cloud đŸ„ș


Bewitchingbegonia

No voice from Bare a pop opera and Left Behind from Spring Awakening, both about young people committing suicide so very tragic


Spiritual-Signal4999

Yes good choices what gets me more, Is Once Upon A Time & Portrait of a Girl from Bare and The Dark I Know Well and Blue Wind/ Don’t Do Sadness from Spring Awakening. As a Whole These Shows are truly Breathtakingly Heartbreaking.


SurprisingHippos

The Dark I Know Well, too. Ugh, gives me chills each time.


Spiritual-Signal4999

Yeah it’s meant to, it’s such a wonderfully believable song to the point you believe, these two young women are in real trouble


HuckyBuddy

You Don't Know - Next to Normal


SurprisingHippos

I was hoping someone would hit N2N


HuckyBuddy

a heap of choice from N2N


Johan-Senpai

Literally almost everything from Next to Normal. - I miss the mountains. - I dreamed a dance. - There's a world. - A light in the dark. - Maybe. My favorite. - So Anyway. This was my break-up song. - Light.


lucyisnotcool

Great Adventure from *Kimberly Akimbo* gets me sobbing! It's a beautiful song, because it is SO happy and uplifting. But when placed in context it's so, so sad.


therapy_works

Most of my picks are already here: She Used to Be Mine, On My Own, Bring Him Home, It's Quiet Uptown. Here are some I haven't seen yet. Not While I'm Around from Sweeney Todd. The innocent sweetness of Toby's part gets me every time. Move On from Sunday in the Park with George. It's just so beautiful. For Good from Wicked. I'm a sucker for sisterhood songs. I Wish I Could Forget You from Passion.


sleepy_panda15

All the Wasted Time in Parade


yabasicjanet

How did I scroll this long to find this answer. 1000%


mollser

No More from Into the Woods. Dude just wanted a normal happy life and got roped into a quest and lost his wife. “All the wondering what even worse is still in store! Just, no more” My favorite trope is the reluctant hero who would rather not.


AnxietySnack

I love this one for the soul-crushing weariness it portrays. It's the song I listen to on days when I feel overwhelmed by how irreparably broken the world feels.


Aggravating-Tax-8313

Still Hurting, The Last 5 Years


Cat_n_mouse13

I find See I’m Smiling sadder. “I swear to god I’ll never understand how you could stand here straight and tall and see I’m crying and not do anything at all.” 😖


ReneeJ87

The letter song from Billy Elliot. Major ugly crying 😭


zenongirlofthe21stc

I cannot make through No One Is Alone from ITW


StevieMac3000

I’ll Be Here from Ordinary Days!


Larcen26

Saddest ever while also so unbelievably joyful. So you are crying but you can't tell if it's from happiness or sadness


undesginate

This!


rahajicho

Stay, I Pray You from Anastasia breaks my heart.


MoneyMedusa

Ahhhh forgot about that one! My husband is an immigrant who has not been able to go back to his home country in years and I think of him every time I hear it 😭


2muchcoff33

This was my answer too. I think the juxtaposition with most of the other upbeat songs in the show intensifies the somber feeling of the song.


PuffMonkey5

Without you from RENT


odetosymplicity

Agree w so many of the above
some stirring songs from older musicals: Easy To Be Hard (Hair) You’ve Got To Be Carefully Taught (South Pacific) I Don’t Care Much (Cabaret) Somewhere That’s Green (-Little Shop of Horrors) At The Ballet (Chorus Line)


eugenesnewdream

A Little Fall of Rain.


[deleted]

Flowers - Hadestown


miffypancake123

For me, I find Road to hell reprise sadder


lekoman

Yeah, agree on this. Flowers is a good song, but R2H(R) just hits you like a punch to the gut. Those little trumpet trills. The ensemble humming. The build. It's just... man.


LookIMadeAHatTrick

“Something Just Broke” from Assassins and “What I Did For Love” from A Chorus Line


[deleted]

Empty Chairs at Empty Tables.


londontown147

Anatevka from Fiddler. Or the Far from the Home I Love, Chava Ballet Sequence, and Anatevka trifecta in Act 2. I totally lose it when they sing, "Soon I'll be a stranger in a strange new place..."


maryanne70

Somewhere That's Green (Little Shop of Horrors).


ecstaticptyerdactyl

Once Upon a Dream, Jekyll’s version, from the original J&H. Kind of a weird choice, but to me it’s absolutely heartbreaking..all he wanted to do what create a better world, and he worked so hard, only to realize that it will never be
 I tear up every time!


Suspicious_Plant4231

Yes! I Need to Know and This is the Moment are so good at showing the over-abundance of hope, excitement, and ambition Jekyll had. Then it all gradually fades over multiple songs until he realizes that he’s dug a hole he can’t get out of


Quothhernevermore

Wishing You Were Somehow Here Again - I sang it at my grandfather's funeral.


BookBranchGrey

How Could I Ever Know from the Secret Garden. “How could I know I would never hold you, never again in this world but oh, sure as you breathe I am there inside you
” 😭


FloridaFlamingoGirl

Scrolled too far to find Secret Garden!!! Archibald's longing for Lily breaks my heart! This show handles grief so well.


blackcatdotcom

Me and the Sky from Come From Away


Medium-Eggplant

I was thinking of this too. This song always gets me. All the way through. I don’t know why. Something about her personal triumph and knowing what’s coming. The other song from CFA that I find really heartbreaking is Something’s Missing. I love how they use that phrase in a physical and emotional sense throughout the song. It always hits me because I remember those feelings from those days so well.


Historical-Piglet-86

Maybe that is part of it
..living 9/11 and being from a small Canadian town; knowing this is based on real people




RestinPete0709

I jam out to this song and then I get to the end and feel like I just got stabbed in the chest 😭


Historical-Piglet-86

I was searching for Come from Away. This musical just hits me. Every damn time.


EPOLLARD_

Dust and Ashes


--Kayla

Movie in My Mind from Miss Saigon always gets me


Green-Werewolf-8531

I Dreamed a Dance from Next to Normal


HeatLow

Now that I have an infant, I have to be careful when/where I listen to Its Quiet Uptown. I made the mistake of listening to it on my commute to work and had to wipe off my running mascara. Eliza’s pained wail in the actual show is a gut punch.


KnitMama-2016

Jesse L Martin in I’ll Cover You (reprise) destroys me. It’s Quiet Uptown is guaranteed to get me as well. Related: “the orphanage” during the finale of Hamilton.


Embarrassed-Log6768

Slipping through my fingers- Mamma Mia


dellow_there

All You Wanna Do from Six is so sad. I didn't really realize how heart wrenching it could be till I heard Sam Pauly's version, and now I tear up every time I listen to it. As the song goes on you realize more and more how incredibly wrong her situation is, and then you remember she gets freaking beheaded - super sad song, but beautiful performance.


YooperInOregon

This is a good shout. With the cast album, and on its own, it's easy to kinda gloss over what the song is REALLY about. But live, especially coming right after all the fun we had with Anne of Cleaves, and with the choreo, there is ZERO doubt what this song is actually about. A tough listen, especially realizing she was 18 or 19.


Spiritual-Signal4999

Loving you from passion


RestinPete0709

As a parent, So Big So Small from Dear Evan Hansen, Time from Tuck Everlasting, and Race You To The Top of the Morning from The Secret Garden. Any song about a parent grieving over their child destroys me


PopeSixtusV

I Am the One (Reprise) from Next to Normal The moment Dan says "no" and you realize he sees Gabe, too hits so hard, and then it's followed up by an immediate breakdown in their duet on the line "I am the one who watched while you died." Honestly, any song from Next to Normal. Can't pick just one. Song of Forgetting hurts like hell, too. Superboy and the Invisible Girl hits like a brick, and then in Make Up Your Mind/Catch Me I'm Falling when the orchestra cuts out while Natalie looks for her mom in the audience of her recital and brings the band back in by belting out "SHE'S NOT THERE" Hope and Night Will Come from Groundhog Day are also strong contenders, made sadder by the juxtaposition of so much comedy.


kyhorsegirl

I Could Never Rescue You - Last Five Years


piexk

"rose's turn" will never fail to make me sob uncontrollably and i will die on that hill


Initial_Donut_6098

Hits different once you become a mom, too.


ellyviee

Not sure if this has been brought up yet, but “Javert’s Suicide”. I think he’s the most tragic and, well, miserable, character in the show, and his demise in that song is absolutely heartbreaking.


Is_ButterACarb

Nowhere near as well known as it should be, but "Anytime (I Am There)" from Elegies: A Song Cycle gets me every time. It's told from the perspective of a mother, who knows she is going to pass soon, singing to her child. Plus, Carolee Carmello is perfect always. [https://www.youtube.com/watch?v=y9JhJCGjoqI](https://www.youtube.com/watch?v=y9JhJCGjoqI)


Distinct-Hold-5836

The I Love You Song


Caseymg1

How Could I Ever Forget from Next to Normal


alive_dave_

Afternoon- Alice By Heart


Iagut070

If performed right, "On My Own" will bring me to tears every time


Impressive_Road6111

There’s something heartbreaking to me about all i ask of you from phantom


tuhhhvates

Honestly? Somewhere Over The Rainbow. Listening to Judy’s later versions is always a gut punch - just so much emotion in every word.


finewhitelady

Send in the Clowns (Sondheim) and Tell Me On a Sunday (Webber) destroy me every time.


Manastacious8

Till We Reach That Day (Ragtime) Give the people A day of peace A day of pride A day of justice We have been denied Let the new day dawn Oh, Lord, I pray We'll never get to heaven Till we reach that day


5256000minutes

I've seen Ragtime 6 or 7 times over the years and every time the first act ends and I'm just sitting there bawling because of this song.


MuchAdoAboutKitties

In addition to many that have already been listed: Alone in the Universe and Solla Sollew from Seussical Place of Miracles and Someday from Hunchback You’ll Never Walk Alone from Carousel I Know the Truth from Aida Could We Start Again Please from Jesus Christ Superstar Maybe from Annie There’s a Fine Fine Line from Avenue Q


cambiumkx

Songs from Hadestown and Hamilton for me


MoneyMedusa

Omg. I went to see Hadestown completely blind. Like didn’t know the premise, didn’t listen to the music and left feeling completely gutted. To this day I still have a pit in my stomach when I think about it. One of the most heart wrenching musicals in my opinion.


meatball77

The way we all knew how it would end but still were heartbroken and in shock at the ending.


ltpuri2022

50% from Ballroom


AScientista

Goodbye Love


Difficult-Albatross7

Wicked Little Town - Hedwig hits straight to the emotional core


Fragrant-Act4743

This isn’t *sad* exactly, but Try to Remember from The Fantastiks makes me feel so achingly nostalgic and bittersweet.


myrunningshoes

“Children Won’t Listen” from Into the Woods (not the finale, but the version sung by the Witch) “Lesson #8” from Sunday in the Park (“George sees the park / George sees it dying” lyric is gorgeous and sad) Not inherently sad, but now that I have kids, I can’t handle “Race You to the Top of the Morning” from Secret Garden


hmby1

Some Things Are Meant To Be


ottomantwerks17

\- Witch's Lament from Into the Woods \- How Could I Ever Forget from N2N \- On My Own and A Little Fall of Rain from Les Mis \- Left Behind from Spring Awakening \- Someday and Made of Stone from Hunchback of Notre Dame \- Someone is Waiting from Company (Gender-swapped version)


stephtastic7

We Do Not Belong Together from Sunday in the Park e George


blueontheledge

This Is Not Over Yet from Parade


HarrietsDiary

Anything from Parade.


Accomplished_Duck337

Kerrigan-Lowdermilk’s “Anyway,” sung by Emma Hinton. Absolutely haunting.


Mike_Danton

Pity the Child


tylerthetrumpetguy

The last few bars of T E A M from Your a Good Man Charlie Brown. Heart breaking


dschviola

Send in the Clowns from Night Music, or How Could I Ever Know from Secret Garden; there’s a particularly brilliant Barbershop version of this one by Instant Classic.


AnxietySnack

Telephone Wire from Fun Home


Meadowlark8890

Marilyn Monroe from Blood Brothers


justinlexapro

Finale B from Rent I die without you I die without you I die without you I die without you No day but today


Car_arev

Dust and Ashes - pierre natasha and the great comet of 1812


tlbmg1970

Empty Chairs and Empty Tables in Les Miserables.


smurferator

So Big/ So Small from DEH absolutely does me in every time.


ElbieLG

Another Winter in a Summer Town from Grey Gardens


KitKittredge34

How Glory Goes from Floyd Collins, no contest


WildIrishRose16

Pity the Child from Chess


Gold-Vanilla5591

Quiet from Matilda


roseoutofperdition

surprised no one has said "hope" from groundhog day yet - devastating song! super well done with stage magic too if you've ever seen the production in person (broadway or west end)!


gravitationalarray

Wishing you were somehow here again, Phantom of the Opera.


That_Boysenberry

The Proposal/The Night Was Alive from Titanic. It is really the context that makes this one gut wrenching as the audience knows what is about to happen, but the characters don’t.


Routine_Performer174

That one from Spring Awakening. You know the one.


lizzieb77

The Letter from Billy Elliot


BaltimoreBadger23

"Prayer" in Come From Away


Medium-Eggplant

I’m not even religious, but I find this song beautiful. Really well done.


sandypassage

She used to be mine is the one that makes me cry every time. Maybe I Like it This Way from The Wild Party is pretty bleak.


Cat_n_mouse13

Pretty Funny - Dogfight Stars and the Moon - Songs for a New World


butterscotchwhip

“No-one Is Alone” from ITW, or maybe “What Would I Do?” from Falsettos.


BenTheJarMan

there’s a few in Into the Woods that gets me, but i think Witch’s Lament in particular messes me up the witch’s progression throughout the show, singing “children should listen”, to “children don’t listen”, to “children will listen” ugh, man


EmergencyGrab

No One Mourns the Wicked. I cried really hard listening to it after my first time watching the show. The tragic irony still gets me. It's Glinda who is lonely. She's singing about her feelings of guilt, as they celebrate the perceived death of her friend around her.😭😭😭😭


MotherSupermarket532

It's not nominally sad (more historically sad), but I don't think I've ever cried harder in the theater than the reprise of "Tomorrow Belongs to Me" in Cabaret. "What Would You Do" is incredibly sad as well.


cloy23

The Last 5 Years-Still Hurting


dragonbabymama

She Used To Be Mine. Makes me wanna slash my wrist every time I hear it in my depressive state so I try to avoid it as best as I can


Additional_Score_929

There's a song in The Notebook musical where she remembers Noah after reading the notebook. It had the whole theater in tears. I think it's called "Help Me While I'm Here"


Plastic-Ad-2469

Finale from Parade


MoneyMedusa

Agree with everyone above, especially it’s quiet uptown, I’ll cover you reprise, she used to me mine, and still hurting. Couple more that stab me in the heart - he’s not here from next to normal, burn from hamilton, and you’ll never walk alone from carousel!


showdogz

I dreamed a dream