Be warned. Umineko is eight games of murder, mystery and hardship. The faint of heart should have a tissue (and a bucket) ready at all times.
Maria's final death in the third arc was absolutely heartbreaking, especially watching her essentially get her dreams that had kept her so... cheerful in the first two arcs get completely smashed.
And in the fourth arc, when Rosa smashes up one of Maria's ceramic rabbits and then tears up Sakutaro, who was virtually Maria's only friend. That scene by itself was heartbreaking in the original Visual Novel, but it's worse in the anime for two reasons: First, because Maria tries to calm her mother down by explaining her "uu" sound is a spell for happiness, trying to remind her of the good times they shared together, and her mother doesn't remember. Second, we get a flashback of Maria and Rosa walking together happily right after Maria asks Beatrice to teach her dark magic to kill her mother. Knowing she does kill her mother in the Visual Novel (and she does so in the next episode) does not soften the blow.
Maria herself underlines this in the scene where she kills Rosa. "But Sakutaro won't be fixed, right? Because Mama, who created Sakutaro, won't accept him. Mama also created me and won't recognise me. So the broken Maria won't be fixed either."
If Maria is able to see Sakutaro as a little boy, then imagine what she must have seen when Rosa tore him apart in front of her. The sounds he makes while Rosa's doing it, while not exaggerated, are still very heartbreaking.
While we are at it, the true origin of Sakutarou, which was easy to miss: We see Ange shocked and crying in fourth arc, after she noticed something in Kawabatas house. She points at it grief-stricken and Amakusa and Kawabata have no idea, what she is pointing at and what's wrong with her. Guess, what she saw: Manufactured lion dolls. Basically mass-produced Saktutarous. Yes, another lie of Rosa exposed; Sakutarou is not hand-made. This sudden realization triggers something in Ange and she becomes able to resurrect Sakutarou, because, well, she has got its vessel.
This Troper thought it was an epic moment for Beatrice though. It showed how much of a Troll she was.
And it get's even worse if you take Shannon=Beatrice=Yasu into account. What we see then is Yasu struggling with him/herself about his/her relationship with George and the fact that no matter what s/he will kill her/himself (to be freed from being a funiture or in order to become a witch). In fact what used to be scary suddenly becomes extremely sad and painful to read, especially since George never gets the chance to say those words indicates that Yasu killed him before he could because he/she couldn't handle hearing them.
Take it a level further: when Battler and the others find the bodies. Yasu completely wrecked the room, smashed the mirrors, couldn't even draw a magic circle and instead just banged, clawed, and scratched the door with her red-painted hands. Try to imagine her mental state at the time.
Then we have their death together in the third arc, where George and Beato struggle together to revive Shannon, and accomplish it in what has to be one of the biggest double Crowning Moment of Heartwarming/Hope Spots ever, only to have the Siesta sisters' arrows promptly skewer both George and the newly-revived Shannon. And George's last words are spent thanking Beatrice for allowing them to see each other again ...ugu...
The ending of the fourth arc can be seen as a huge Crowning Moment Of Awesome for Battler...but after playing through Chiru, think about what the context behind it really means...then it suddenly becomes a LOT more sad.
Now try watching the scene in episode 6 right after Battler "imagines" the plate of cookies and Beato and everyone else joking around, then afterward when the "illusions" disappear and only Battler and Beato are left standing there having a heartfelt talk about chick Beatrice. Beato says to think of her as her daughter, cue "Thank you for being born" RIGHT AT THAT MOMENT. Instant buckets of tears
Thank You For Being Born. Play it during any sad scene anywhere and you'll become a sobbing mess. Even the last preview for the anime manages to do so with this.
I'm pretty sure I'm alone on this, but there was this one line in the epilogue of Episode 5 where Bernkastel or Lambdadelta offhandedly reveals that the Seven Sisters of Purgatory are not ancient ceremonial weapons of execution, but hokey occult tchochkeys sold on the cheap in New York. It's weird, but even though I don't usally get emotional in the slightest over things like this, and even though they never really made an impression on me as characters, that one thing just got to me, you know?
From the same arc; the end of the trial. Natsuhi has been horribly framed for both murder and adultery, both Beatrice and the Kinzo who supported her being revealed as a delusion she created out of sheer despair and loneliness, she gets beaten up by Eva, both her husband and daughter are dead, and nobody (except Battler, who knows that she's innocent for sure, but was recently impaled) is trying to protect or support her anymore; everyone's buying Erika's lie. She finally breaks down sobbing completley, and starts talking to the man from 19 years ago and crying and asking him what else could he want from her. The music playing during that scene, while breathtakingly beautiful, raises the Tear Jerker level Up to Eleven.
This Troper is surprised that no one has mentioned Hideyoshi's death in the Third Arc yet. That fact that even Eva-Beatrice seemed to be at least mildly affected by it should tell you something.
The few minutes before his death in the fifth arc are worse; after George is killed, he is shown as stable and supporting of his wife as she falls to pieces. Later, he retires to an "empty" guest-room under the pretense of getting some rest, talks to himself in his normal cheerful way for a few moments...and then falls onto the bed, sobbing uncontrollably. It's both startling and heartbreaking, especially considering his character's attitude up until then.
Natsuhi's narration makes it a lot worse, considering she's in just as terrible a situation, and despite him being one of the few family members she actually gets along with, if she reveals that she's there and saves him from the culprit her kidnapped husband gets murdered (and their daughter's already dead). And then afterward she gets blamed for the whole thing, and Krauss is implied to be dead anyway. Duel Tear Jerker for the both of them, then.
That translation is actually wrong. The real translation is instead of "because I can't accept that I've lost everything," it's "I don't care if I lose everything, so, please..." The line before that references a "burning pain." Sob.
A lot of moments in a fourth arc qualify. First, Ange's past and story is particularly painful to read through- especially when right after a scene in which we see Ange happily playing with the stakes and Maria, we are treated to a scene when she gets bullied by her classmates in such a painful way that is already heart-rending, but then she reaches her breaking point, and demands from the stakes to kill them- when they can't and try to explain, she denies them all and kills them, and Sakutaro the witch Maria as well- meaning, her only friends. Then, after they all dissapear, when she finally stands up and reads up the humiliating letter the bullies were coercing her into reading, she breaks down in the middle, and asks for someone to let her die- seeing this happen to Iron WoobieAnge, of all people, is really painful and sad. Second, the entire scene where Maria kills Rosa really shows just how broken and tragic they both are in their own ways, in particular if we buy the interpretation that it's Maria's dream; meaning, this is how Maria sees her mother- nothing but an ugly, abusive monster..
Three words : "Who am I?" For some reason, this Troper is always moved to tears by that line.
However, Mammon's ridiculously exaggerated "frieeeeeeeend" was so artificial that it pushed the deal from Tear Jerker to Narm.
Ange being turned into a delicious hamburger. You know what I mean.
The First Twilight in Legend. Jessica finding her father and Battler finding both of his parents dead were bad enough, but. . . SHANNON!
In that same scene in EP 1, George was asked by his father what was the last thing he saw on Shannon. His response, "her beautiful smile." With his father soon replied, "Shannon wanted to leave that smile for you." But the real Tear Jerker came when George asks him about the diamond ring that was given in their last meeting and its current location. The answer, it was located on Shannon's left ring finger like she was engaged.
Also the way Hideyoshi obfuscates the relationship in front of Eva and comforts George by saying "Whoever gave that to her must have made her real happy..."
EP 6, right after Jessica kills Kyrie. She just starts sobbing about how she couldn't give Kanon up, even if that meant killing Kyrie and it was just sad to see ol' tough Jessica completely break down and wonder if she did the right thing...
EP 7, Ange being turned into hamburger, yet again - except this time, she isn't smiling and urging her brother to go on. She's screaming in agony because of the "truth" she's just learned, which involved finding out her mother hated her, and that Eva actually was the one who cared for her. Fuck you, Bernkastel.
It's just as bad from Beatrice's perspective. She finally gets Battler to see her as she wants him to see her...then throws it all away in order to make him reach the truth. Playing through the second time around, her pained facial expressions during her Face-Heel Turn really sell the scene.
EP 6 also has Kanon reflecting on his life and the bonds he's made with the family—especially the unpersonable ones like Kinzo, Natsuhi, and Krauss; and the ones he doesn't get along with, like Gohda—while running to rescue Battler from the closed room.
EP 7, most of Yasu's story. Waiting for a Childhood Marriage Promise that will never be fulfilled, being constantly abused by the other Servants, etc. Also, the true reason behind the epitaph and what happens once it's solved.
The grand ending of the series in EP 8, in which Battler dies and gets to be Together in Death with Beatrice and his family, complete with reunion scene and Call Back to EP 3. I think my heart just broke in the best possible way.
EP 7, Will and Lion being killed by Bern.
Averted later in EP 8 when They are shown to have...won. Somehow.
They didn't. Lambda just saved them.
EP 6, The man is a jerk, but This Troper can't be alone in feeling sorry for Rudolf after the first twilight, in which both Kyrie AND (more importantly) Battler are killed.
EP 5: "Thank you, liar, goodbye... I'm sorry
EP 8: Most of the scenes unlocked by solving the quizzes.
Also in EP 8, both the Trick and the Magicending, the magic ending in particular. Of course warning for major spoilers.
This troper, really digging the song played during the magic ending, looked up the lyrics for Byakumu no Mayu. While the entire song is really bittersweet, one line in particular stuck with this troper: "Quel giorno, quanti misteri avrei dovuto risolvere per poterti portare via?" This translates out to "That distant day, how many mysteries would I have had to solve to save you," making the song sound like a lament from Tohya!Battler after he realized the truth.
What makes this series so heart-wrenching is that once you've been through one and a half episodes, you begin to realize that each and every Moment Of Awesome and most Heartwarming Moments will inevitably be followed by some horrible tragedy that screws over EVERYTHING achieved in previous awesome/heartwarming moment(s).
On the topic of what makes this series so heart-wrenching, let's discuss what most of Chiru up to its ending implies. Even though Battler was able to deduce Yasu's mystery by the end of End, he was still unsuccessful in solving her mystery by the time she disappears. However, solving Beato's mystery is more than just "who is Beatrice;" it's also discovering the secrets as to why Beatrice is the way she is. All of Chiru implies that because Battler didn't solve Beato's mystery, and why Yasu put up that front to begin with, Yasu ended up killing herself or dead somehow in Rokkenjima Prime.
Rosa's ending with Battler in Ougon Musou Kyoukuafter she kills him over the letter she suspects him of planting.Laughing Mad, she screams at Beatrice, and to Maria to run and escape, with the implication left hanging that neither of them did.
EP 8, Ange's suicide. "It couldn't have looked like anything. Just like how the death of a single lonely girl who rejected the world... didn't matter to anyone in the world." This Troper was full-out sobbing, a first with any kind of novel, game, or series.