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Tear Jerker: Into the Woods
First there's "The Witch's Lament" when Rapunzel gets crushed by the Giantess:
"Children can only grow/ from something you love/ to something you lose...."
And then there's "No One Is Alone", where the characters realize they're not in a fairy tale anymore:
"Witches can be right. Giants can be good. You decide what's right. You decide what's good. Someone is on your side/ someone else is not/ While we're seeing our side/ maybe we forgot: They are not alone. No one is alone."
And the finale, especially the Witch's reprise of "Children Will Listen":
"Careful the things you say / Children will listen / Careful the things you do / Children will see, and learn / Children may not obey / But children will listen / Children will look to you / for which way to turn..."
Another song by the Witch: "Stay With Me". She sings said song when she finally catches up to Rapunzel after she learns that she had spoken with one of the princes.
This part will make you want to hug your mom:
Who out there could love you more than I? What's out there that I cannot supply? Stay with me...
When the baker finds Cinderella silently kneeling over the destroyed remains of her mother's grave. The tree that granted all of her wishes was killed, and her dreams crushed.
Rapunzel's entire history. Locked up in a tower, banished to the desert, betrayed by her prince and then crushed underneath the Giantess. It's hard not to shed a little tear for her.
The ghost of the Baker's Wife's entrance just before the reprise of "Children Will Listen".
Baker: Maybe I just wasn't meant to have children. Baker's Wife: Don't say that, of course you were meant to have children.
It is kind of sad when Little Red Riding Hood discovers that her grandmother and the rest of her family are dead.
Actually, just about every character death in the second act, excluding the Narrator and the Giantess.
The Witch's first response to Rapunzel wanting to stay with her prince and children.
The Witch: You're all I have left.
To be fair, her actions before her transformation did result in Rapunzel's rejection.
"Ask a wolf's mother."
When The Baker leaves the rest of the survivors, and then the duet with his father's ghost
The last half hour or so is just a non-stop tearjerker.