History TearJerker / IntoTheWoods

* The fact that the last conversation the Baker and his Wife has is a fight.

* This conversation:
-->'''Little Red Riding Hood:''' A wolf and a person aren't the same thing.

* "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.

* Actually, just about every character death in the second act, excluding the Narrator and the Giantess.

** In the film, there's the part where Jack learns that his mother is dead. The Baker has to tell this kid that he's alone in the world and then explains that the Stewert did it. Jack immediately starts planning to kill the Stewert 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 Stewert did was wrong!" you can make out that he really ''is'' crying. The fact that Jack is actually played by a kid and not an older actor doesn't help matters at all.

* "Ask a wolf's mother."

* In the film when the Witch briefly thinks the Baker and his wife failed to get the right ingredients. In most productions the Witch is pissed, but in the film she sits down and breaks into tears. Meryl Streep said in interviews she felt the Witch's only motivation in the film was to prevent losing her daughter, and it comes across here.

* In the film, the Baker's Wife finding out about the curse is heartwrenching, 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.

-->''Who out there could love you more than I? What's out there that I cannot supply? Stay with me...''

** Averted in the 2014 film, where she is last seen riding off with her faithful prince.

* The film's version of "Cinderella at the Grave." Especially the background music as Cinderella's iconic dress and slippers are formed by magic.

* In the 2014 film, Rapunzel reuniting with her prince.

* The last half hour or so is just a non-stop tearjerker.

* When The Baker leaves the rest of the survivors, and then the duet with his father's ghost

* ''IntoTheWoods'': First there's "The Witch's Lament" when [[spoiler: Rapunzel gets crushed by the Giantess]]:

* 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.

* The [[spoiler: 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.

--> '''The Witch''': You're all I have left.

* The last half hour or so is just an non-stop tearjerker.

* When The Baker leaves the rest of the survivors, and then the duet with his father's ghost

* "Ask a wolf's mother."

--> "Giants can be good. Witches can be right. You decide what's good. You decide what's right. 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."

** To be fair, her actions before her transformation did result in Rapunzel's rejection.

-->Baker's Wife: Don't say that, of course you were meant to have children.

----

* ThisTroper absolutely dies every time he hears the Baker, repeating TheNarrator's opening words, say "With his wife."
* This troper, who played the Mysterious Man, was given the direction of [[spoiler:kissing the Baker on the head before he vanishes near the end of ''No More.'']] I had trouble stifling my ''own'' tears when I did so, and from what I heard from my family later, so did several members of the audience.
* This troper choked up at "No More" but the end when the Baker's Wife comes out to reprise "No One Is Alone" holds the distinction of being the first play to ''ever'' make this troper cry.

* This troper played Rapunzel, and it's not "Stay With Me" itself that made her burst into tears every night, it was the actress playing the Witch's quiet, heartbroken delivery of the line ''"You are ashamed of me!".

* Rapunzel's entire history. Locked up in a tower, banished to the desert, betrayed by her prince and then [[spoiler: crushed underneath the Giantess]]. It's hard not to shed a little tear for her.

* 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.

* 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.

* This troper played Rapunzel, and it's not "Stay With Me" itself that made her burst into tears every night, it was the actress playing the Witch's quiet, heartbroken delivery of the line ''"You are ashamed of me!".