For the record, I will NOT be including productions that started life as a film, so no Sister Act or Newsies, and no Disney productions so no Lion King or Beauty and the Beast. They deserve lists of their own.
Also, spoilers.
10: Memory (Cats)
This is one of the classic heartbreak songs of Broadway that even the awful Cats film couldn't ruin. The song is about remembering the time when things were better and Grizabella was young and beautiful. It invokes a sense of sadness at what she lost, and pared with the melodic tone it moves the heart every time.
9: Not My Father's Son (Kinky Boots)
This irreverent play is a celebration about being different, but being different comes with its own pain. This song is about not being able to live up to a father's expectations, despite wanting his approval. This is a pain most men go through, no matter their situation, so this becomes a dagger right to the daddy wound.
8: I'm Not That Girl (Wicked)
Usually the pick for Wicked is For Good, the finale and conclusion of Elphaba and Galinda's relationship, but I'm going to argue for I'm Not That Girl. Another song for the outcast, this is Elphaba morning the fact that she will never be the one Fiyero will ever want to be with (Even though he does later). It's a heartbreaking song about being rejected for things you can never change, whether you'd want to or not.
7: Little Fall of Rain (Les Miserables)
Honestly pick a song from this musical and you will probably burst into tears (Except Master of the House, that one's just pure fun) but I'm going with Little Fall of Rain. Here Epanine sacrifices herself to protect her beloved Marius, despite him being in love with Cozette. In her last words, she sings how all she wants is for him to be with her till the end, and that despite the sadness at least the rain will make the flowers grow, and thus something beautiful can come from this one moment.
6: For Forever (Dear Evan Hansen)
Quick synopsis: Evan is a shy depressed kid starting a new year at school with a broken arm. On the first day the school burnout swipes one of his letters he wrote for therapy then later that evening commits suicide. When the letter is found on him it's assumed that he and Evan were best friends. Evan, not wanting to tell grieving parents that the reason his letter was in their son's pocket was due to an act of bullying, decides to go with the assumption and procedes to make up a story about their friendship. Now if this show was purely a comedy (and a bad one at that) this story would probably be played up for laughs with exaggerations, things that can be easily misproven, and a lot of nervous stammering. Instead though Evan tells a story of them going out to the woods and climbing a tree when he fell off and subsequently broke his arm. The story is beautiful in the sincerity Evan pours into it, making the listener think that this was the day he wanted instead of the day he actually had, where he did go out to the woods and climb a tree but jumped off in his own suicide attempt. Evan rewrites his own story as a what if these boys had been friends, and what that friendship would've meant to each other.
5: Somewhere That's Green Reprise (Little Shop Of Horrors)
Somewhere That's Green is a pretty song in and of itself, as Audrey describes her want for a life outside the dirty city where everything is green and pretty. In the film that most people would be familiar with, Audrey and Seymore escape the flesh-eating plant and get their fairytale life. In the play however, Audrey is killed by Audrey II, and has a soliloquy about how she will become the green place she always wanted, as long as Seymore is there to take care of her they will always be together.
4: Doubt Comes In (Hadestown)
I talked about Hadestown recently but this song is probably the most killer (Get it, cause it's about death?) in it Orpheus and Euridice are trying to walk out of the underworld, their success based on weather or not Orpheus can lead them out without turning around to see if his beloved is still following him. The song is Orpheus in his head, debating weather or not Hades' promise is real and if Euridice is even still behind him. While Euridice is trying to encourage him, the music stings, indicating the moment when his doubt finally gets the better of him and he turns around. The moment is as heartbreaking now as when it was first penned thousands of years ago.
3: It's Quiet Uptown (Hamilton)
Another play where you can pretty much pick a song and cry, Hamilton's most tear-jerking song describes the grief parents feel after losing a child. Alexander wanders New York in a daze, his charisma completely eradicated by the loss of his son. On top of that we still have the fallout of the Reynold's pamphlet, where he confessed to infidelity on his wife. In this song though not only do we get their grief but her forgiveness, seeing a slight glimmer of hope in an extremely dark time.
2: You Are Not Alone (Into The Woods)
Even a comedy can have its moments, and the finale of Into the Woods is no exception. The baker, so scared to be a parent, holds his child and hears his wife's voice helping guide him in the first few moments of this new life. The entire idea that even when you feel alone that you aren't is something everyone at one point or another needs to hear, and this song takes us right back to those moments.
1: I'll Cover You Reprise (Rent)
This list has covered loss a lot (And a lot of reprises) but this funeral hymn takes the cake. Originally sung as a celebration of Angel and Collin's love, Collins now sings it at Angel's funeral, both celebrating and mourning his partner. The upbeat lyrics juxtoposed to Collins' tone is enough to rip your heart out and make you pull your beloved close to you.
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