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1!!Theater
2* The Baker and his wife's grief when the Witch tells them that they can never have children. The wife cries out ''"No!"'' and when she and her husband reach out for each other, the Witch just [[KickTheDog pushes their hands apart with her staff]], all while cackling.
3* First there's "The Witch's Lament" when Rapunzel gets crushed by the Giantess:
4--> "Children can only grow/ from something you love/ to something you lose...."
5* And then there's "No One Is Alone", where the characters realize they're not in a fairy tale anymore:
6--> "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."
7** What is the lead in to the song? Red saying "Mother will be so disappointed." The first line of the song is from Cinderella (''Mother cannot guide you, now you're on your own''). She lost her own mother when she was probably Red's age...and it's clear that she might be remembering her own mother.
8** The interaction between the Baker and Jack in the middle of the song is also quite devastating, from Jack's disbelief that his mother is dead to the Baker, even after 'No More', clearly still struggling to work out exactly how to be a father (or at least a father-like figure) trying to give advice. Even the fact that Jack's first instinct after learning of his mother's death is to find and kill the steward who killed her (despite her death appearing to have been entirely unintentional on his part) is a sombre reminder that this isn't the same dopey carefree boy we met at the start of the show. And it takes a while for the Baker to even give Jack a reason why he ''shouldn't'' kill the steward.
9* And the finale, especially the Witch's reprise of "Children Will Listen":
10--> "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..."
11* 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.
12** This part will make you want to hug your mom:
13--->''Who out there could love you more than I? What's out there that I cannot supply? Stay with me...''
14** "Stay at home. ''I'' am home."
15* 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.
16* 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.
17* The ghost of the Baker's Wife's entrance just before the reprise of "Children Will Listen".
18-->'''Baker:''' Maybe I just wasn't meant to have children.\
19'''Baker's Wife:''' Don't say that, of course, you were meant to have children.
20** ''"Sometimes people leave you / Halfway through the wood / Do not let it grieve you / No one leaves for good..."''
21*** After [[Creator/StephenSondheim Sondheim]]'s passing in November 2021 there were many tribute posts across social media using these lyrics.
22* It is kind of sad when Little Red Riding Hood discovers that her grandmother and the rest of her family are dead.
23* Actually, just about every character death in the second act, excluding the Narrator and the Giantess. ''Hell,'' even then they're sad in their own way.
24** Jack's Mother dying is surprisingly hard-hitting, even when played for laughs. She's killed for actively defending her son from someone looking to kill him, her killer refuses to take responsibility for what he's done, and just before she dies she makes the Baker promise to find and protect Jack...which only makes things worse when Your Fault comes along and the Baker is briefly only too happy to just give Jack up after having finally hit the DespairEventHorizon.
25* The Witch's first response to Rapunzel wanting to stay with her prince and children.
26-->'''The Witch:''' You're all I have left.
27* This conversation, right after Little Red Riding Hood comments that the group has repeatedly watched people die:
28-->'''The Witch:''' Since when are ''you'' so squeamish? How many wolves have you carved up recently?
29-->'''Little Red:''' A wolf's not the same thing--
30-->'''The Witch:''' Ask a wolf's mother.
31* "No More" is especially heartbreaking. The Baker is trying to cope with his wife's tragic death, but he can't handle it. Instead, he tries to run away, [[IronicEcho just like his father]] had done and is stopped by his father's ghost. His father voices what it was like for him when he ran away, trying to dodge responsibility and figure out how he was going to survive.
32-->''No more giants waging war\
33Can't we just pursue our lives with our children and our wives\
34'Til that happy day arrives how do you ignore?''
35** "No More" adds a whole new dimension to the Mysterious Man/Baker's Father, who spends the whole first act of the show as a kind of TricksterMentor. He's jolly and riddling, often speaking in silly rhymes...only for this song to reveal that he spent at least thirty years absolutely hating himself for what he'd done to his family, and was never able to make peace with his actions or resolve his pain.
36* Throughout the whole musical, the phrase "I wish," along with a two-note motif, keeps reappearing; it opens the first and second acts, and characters use the phrase many times. But the recurring theme becomes absolutely heartbreaking during "No One is Alone." Little Red Riding Hood, who has just discovered that her Granny--that is, her last living relative--is dead, is suddenly forced to change her whole understanding of morality, good and evil, and justice by helping the survivors kill the Giantess. As Cinderella sings, Little Red manages to choke out the phrase "I wish..." as the two-note motif plays lightly on a flute. The poor girl sounds so ''destroyed.'' And we can only imagine what she might be wishing for--for her mother and grandmother to still be alive, to somehow fix everything that went wrong...but these wishes can never come true.
37** Plus Cinderella's response to Little Red is just a quiet and defeated "I know". Cinderella has just abandoned her own "happy ever after", having told the Prince that their marriage is done upon learning of his infidelity, and has now learned that wishes won't fix everything, nor will getting them necessarily make you happy. Since she now effectively has to be an authority figure to Little Red, her "I know" is quite literally the only moment she's given to grieve for all she won and then lost.
38* The fact that the last conversation the Baker and his Wife have is a fight.
39** And not just a fight. One of the very last things the Baker hears his Wife say to him is "[[{{Foreshadowing}} Will only a giant's foot stop your arguing?!]]" and there's a brief silence as everyone is too stunned to speak. When the Baker learns that Jack buried her in one of the giantess' footprints, the exact same brief silence returns.
40* The Witch's words to Rapunzel after she becomes beautiful again. "This is the real me!" She just sounds so ''happy'', like she genuinely believes that her appearance was all that was causing problems with their relationship.
41* Cinderella finds out from the birds that her husband was being unfaithful with the Baker's wife. She knows the giantess killed the poor woman, so she doesn't tell the baker. When the Prince appears in the woods and recognizes her, however, she asks him if she was his only love or if there were more. He actually has the decency to look ashamed. In the 2022 Broadway revival, he rambles about how he actually never asked to be king and doesn't know what his true self even is, and then accepts their effective divorce with quiet words:
42-->'''Prince:''' You'll always be my girl at the ball.\
43'''Cinderella:''' You'll always be my faraway prince.
44* The Witch bringing Jack to the Baker, Cinderella and Little Red, which is also where she has to break it to the Baker that his Wife is dead.
45-->'''Jack:''' I'm sorry, sir...I came upon her and she was under a tree...\
46'''Witch:''' He was sobbing over her like she was his own mother.
47* Something of a Fridge Tearjearker, the only time Rapunzel and the Baker even see each other is seconds before she gets crushed. Neither of them ever find out that they were brother and sister, though there have been productions that imply the Baker works it out upon seeing the Witch's reaction.
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50!!Film
51* The Baker's Wife finding out about the curse is heart-wrenching, no matter how brief that sob was. The poor woman just got told that because of something she had nothing to do with, something that wasn't her or her husband's fault, her greatest desire will never, ever be a possibility.
52* "Cinderella at the Grave" with Cinderella crying just before her dress and slippers form. Creator/AnnaKendrick does a pretty good job as you can just see the pain in her eyes. Especially with the BackgroundMusic as Cinderella's iconic dress and slippers are formed by magic.
53* When the Witch briefly thinks the Baker and his wife failed to get the right ingredients. In the stage productions the Witch is pissed, but in the movie she sits down and breaks into tears. Creator/MerylStreep said in interviews she felt the Witch's only motivation in the movie was to prevent losing her daughter, and it comes across here.
54* While Rapunzel's crushing death is averted in the film, she is last seen riding off with her faithful prince. While still ''less'' sad than in the play, it still manages to be sad for a completely different reason.
55* "No More" the tragically beautiful song between the Baker and his father is cut, but we still have the Baker alone sobbing over the scarf he gave his wife right before she died.
56* The part where Jack learns that his mother is dead. The Baker has to tell this child that he's alone in the world and then explains that the Steward did it. Jack immediately starts planning to kill the Steward for what he did. What really sells it is how Jack talks. While he acts tough, you can tell he's doing his best to fight off tears. After he chokes out, "What the Steward did was wrong!" you can make out that he really ''is'' crying. The fact that Jack is actually played by an actual child and not an older actor doesn't help matters at all.
57** What hurts the most is that the interaction starts off happily, with Jack telling the Baker he can't wait to let his mother know that he killed the giant. When the Baker breaks the news, Jack's last moment of innocence comes with the childlike question, "Can no one bring her back?" asking an adult for the reassurance that both of them know won't come.

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