!As this is a Tearjerker page, all spoilers ''will'' be left unmarked. Administrivia/YouHaveBeenWarned!

[[quoteright:350:https://static.tvtropes.org/pmwiki/pub/images/ep47hinamoricries.png]]
[[caption-width-right:350:[[TheWoobie Hinamori]] becomes just one of many tragic tales in this series.]]

For all its [[Awesome/{{Bleach}} awesome]], [[Funny/{{Bleach}} hilarious]], [[Heartwarming/{{Bleach}} comforting]] and [[NightmareFuel/{{Bleach}} creepy]] scenes, did you really think ''Franchise/{{Bleach}}'' wouldn't have its gut-wrenching moments either?

[[foldercontrol]]

[[folder: Agents of Shinigami Arc]]
* Knowing what is shown later, Isshin pretending that he didn't know that he and his surviving family was almost killed in episode 1 with him still being too weak to stop it must have been horrifying. How long has he been keeping up that brave front?
* When Orihime's brother Sora is purified. Not by a Zanpakutou, as is normal when dealing with Hollow, but by his love for his little sister. She felt guilt over his death because she had been angry with him and did not send him off properly on the day of his accident. So when she wishes him a safe journey for the last time it really gets the tears flowing. [[https://youtu.be/YSW1-qa8Q5I?si=7ZJxZrsJUgRFpo6l Going Home]] doesn't help at all
** Ichigo's "[[KnightTemplarBigBrother Do you know why big brothers are born first...]]" speech.
* Another one would be the always tough [[{{Bokukko}} Karin]] breaking down completely during Chad's introductory mini arc, as she's overwhelmed by Shibata/the parakeet's memories and the strongest one ''happens'' to feature [[KickTheDog the gruesome murder of Shibata's mother]].
--> '''Karin''' ''(to Ichigo)'': I'm begging you, Ichi-nii! Please save that kid! Tell him that he can meet his mother if he goes to the other side! Don't let him be alone anymore...!
** Yuichi Shibata in general. He quite happily agrees to being sent to the Soul Society when told that his mother is there waiting for him. His last appearance was in the Soul Society arc, in which he lives with a foster family and hasn't found her.
* The scene after Ichigo battles the Grand Fisher. Ichigo's mother appears to him, tells him how much he's grown...and then tells him never to lose that smile. The irony of this request makes [[PerpetualFrowner what the audience had long taken for granted]] suddenly become very sad indeed.
* Before then, we get treated to a scene of Karin being alone while other children are picked up by their mothers at school.
* Memories in the Rain (One thing, just one thing / that I couldn't protect / my fight still continues, for my pride / No time to cry / I can cry later / Right now I can only swear to the June rain).
* The Don's realization of what he was really doing. Although it was a short scene it was sad to see such a kindhearted guy see that he was screwing up really bad. "Paved with good intentions" indeed.
* It's easy to forget it as he develops into a LovableSexManiac ButtMonkey, but Kon has genuinely tragic origins: he was explicitly conceived to serve as a weapon against Hollows, but due to ethical concerns he was slated to be discarder ''the day after his birth''. He saw all his siblings die and managed to escape their fate by sheer dumb luck, but had to live with the knowledge he could be identified anytime. When he gets into Ichigo's body, that's the first time he can have fun, and it almost ends up killing him when Kisuke learns what he is and flatly declares his intent to destroy [[ItIsDehumanizing it]].
* Rukia's goodbye as she's taken back to Soul Society. Ichigo lies on the ground bleeding to death but he grabs Byakuya's leg. As Byakuya threatens to cut off Ichigo's arm, Rukia runs up and kicks his arm away, scolding him for daring to touch her brother. Ichigo reacts with hurt and tries to get up to stop her. She shouts at him not to move and her facade cracks enough to reveal tears in her eyes. She demands he not follow her as she walks through the portal to Soul Society. Then, Ichigo realizes that she left to face ''execution'' in order to save him and screams.
** [[FromBadToWorse It gets a little worse]] in the following chapter. Ichigo gets back to the school, only to discover that almost nobody remembers Rukia save for Chad and Orihime. A guy even is using her seat. When she got back to Soul Society, she was erased from everyone's memory. And she knew it would happen the moment she stepped out of the Human World, considering how Shinigamis are not supposed to be known by humans and yet her case was a special one. That makes her conversation with the girls some chapter before, when she realizes that she's going to have to leave everybody, even more painful.
[[/folder]]

[[folder: Soul Society Arc]]
* There's the one when Rukia had her flashback about Kaien Shiba and started crying and saying that she hated herself for killing him, not being able to save him from the Hollow and for her own weakness.
* When Yoruichi defeated Sui-Feng, and we see [[IceQueen Sui-Feng]] practically ''bawling'', asking why Yoruichi didn't take her as well when she ran away.
* Another sad Rukia scene was when she said/thought "thank you" to all her friends as she stared the big bird of death in the face, convincing herself that she was satisfied with her fate. '' "No sadness... No pain... No regrets. There is... nothing for my heart to linger in this world..."''
** Orihime had a similar scene in the Hueco Mundo arc, where she tells Ulquiorra that she is not afraid to die because her friends came after her and her heart is with them. Meanwhile, her friends are fighting to get to her.
* Most of Hinamori's character arc in the Soul Society arc, the high points being when she saw Aizen dead, when she fought her adoptive brother Hitsugaya crying and claiming she didn't know what to believe in anymore and when Aizen stabbed her to almost death.
* And there's also Chapter 98 of the manga, with Renji and Rukia's backstory and Renji's reaction after losing to Ichigo, begging him to beat Byakuya and save Rukia's life.
** This became anime Episode 32. All of it. Poor Renji. It's also heartwarming, because even though he CantCatchUp to Rukia, he loves her just the same.
* Then there's the fight between Renji and Byakuya from Chapters 140-144. Renji has strived so hard to obtain Bankai for the sake of defeating Byakuya, only for his captain to effectively destroy it before showing his own Bankai while Renji is bound with a Kido spell. Poor Renji is barely left alive and he endures Byakuya's infamous speech on the monkey and the moon, where he basically tells Renji that he'll never be able to reach him. Even so, Renji ''still'' tries to take down Byakuya, despite being on the verge of death, only to collapse from his injuries.
* When Byakuya told Rukia the ''true'' reason why she was adopted into the Kuchiki clan...
** The performances of [[Creator/RyotaroOkiayu Byakuya]] and [[Creator/FumikoOrikasa Hisana's]] (Japanese) VA's in the anime were what really made that scene so heartbreaking. Seeing Byakuya display that much emotion... just wow.
*** Considering that he's voiced by Creator/RyotaroOkiayu and one of Okiayu's specialities is voicing {{Sugar And Ice Guy}}s, technically it's still not THAT big of a surprise.
* When Mayuri blows up his three subordinates. What really made it upsetting wasn't so much the bombing, but the one or two page flashback with the new recruit in Squad twelve. All he wanted was to be a seated officer to impress Hinamori, but that was never Mayuri's plan in the first place... In his final moments you see him reaching out to his captain, then his arm distorting grotesquely, and he blows up. Why, Mayuri? Why?
[[/folder]]

[[folder: Hueco Mundo Arc]]
* Orihime's goodbye to Ichigo before she went to Las Noches with the Arrancar. ''"You know, Kurosaki-kun, I wanted to do loads of things. I wanted to be a teacher, I wanted to be an astronaut. I wanted to go to an ice-cream shop and order everything. I wanted to go to a donut shop and do the same. Oh, if only I had five lives! Then I could be born in five different towns, eat five lifetimes of food, have five different careers... And each time... fall in love with the same person, five times."''
* If Tatsuki's scream of "Aren't we friends?!" didn't get make you sob, then the expression on Ichigo's face as he looks up at the hand Orihime healed before she left will.
** What about the scene when Tatsuki punched Ichigo and his head hit the window? All the emotions built up in this scene hit the roof at that part. Then we had the flashbacks where she protected him as a young kid...
** And finally, we have Ichigo saying telling her, Keigo, and Mizuiro to stay away from him, and Tatsuki's scream of anguish while he's walking away.
*** Come to think of it, that whole scene was just one giant Tear Jerker.
* When Ulquiorra has stabbed Ichigo through the chest, then a little while after number four has left, we see Nel with an utterly broken look on her face, going over to Ichigo, all the while sobbing "Itsygo...". The fact that his eyes are open and unmoving is heartbreaking.
* As of Chapter 349 of the manga? Ishida has lost a hand, Ichigo is dead, Orihime is about to [[HeroicBSOD completely shut down in pain and horror and guilt]] since her powers don't seem to be enough to save him and she doesn't know what to do anymore since nothing works... and the one to blame for everything is Ulquiorra.
* Chapter 353. Ichigo comes back from his Hollow state, recognizing Orihime and Ishida. Ulquiorra pulls out Ichigo's sword from Ishida's abdomen, tosses it to Ichigo and demands that they finish their fight. Ichigo offers to cut of his limbs for the sake of fairness since Ulquiorra is missing an arm and has a maimed leg. It's then revealed that Ulquiorra is actually dying and can't regenerate anymore because his interenal organs were damaged by Ichigo's cero perviously. In his last moments, Ulquiorra reaches out to Orihime and asks her if she finds him frightening, mirroring their conversation before Ichigo arrives in the tower. She replies with tears in her eyes that shes's not and reaches back for him. His body dissolves before they can touch.
* Chapter 354 Ulquiorra's last thoughts as he dies add to the AlasPoorVillain vibe HUGELY: "Oh, I get it. This is it. This here in my hand. The heart..." This is all the more tragic since he never understood bonds like friendship and love previously and constantly questioned them. When he finally does understand, by recognizing that he shares such a bond with Orihime, despite all that he did, it's already too late. Also, Orihime is apparently distressed by being unable to reach him since she keeps trying to grasp his body even when his hand turns to ash.
* Nnoitra's death in the anime. It doesn't make him any more likeable, but still...his inner monologue shows how much pain he really feels. Then, as he falls, he looks at child Nel right before dying. She can't remember him, but it seems like her subconscious does. When she says his name, it almost seems like she's lamenting over the fact that she couldn't save him from his violent ways.
** The music in said scene...
* Chapter 199, 'Ugly'. It lasts around five pages, but in those five it basically tells you up-front that despite the powers and adventures, Orihime is just a sixteen year old girl.
* Nel's anguished cries in the anime when Nnoitra is torturing Ichigo.
* The end of Nel's backstory, where she's wounded in child form, and goes to sleep as Pesche and Dondochakka swear to protect her from now on.
* Grimmjow's backstory. It's just so...lonely. He thinks the other Hollows are cowards for giving up because he's been through so much shit. And there's the kind of Jesus-sounding "Become my flesh and blood and see what lies ahead." It's even called Historia del Pantera y sus sombras, "History of the Panther and his shadows." Then he gets lowered, very softly, to the ground by Ichigo, who tries to convince him to give up so they can fight again, and Grimmjow KEEPS TRYING. And then Nnoitra comes and Ichigo looks extremely shocked, and then protects Grimmjow from dying, which all seems like Ichigo wants Grimmjow and him to only be rivals, not enemies.
[[/folder]]

[[folder: Turn Back The Pendulum Arc]]
* The last chapter of the flashback arc was full of this. Urahara wakes up in his lab after a restless sleep and the very first thing he sees is one of his best friends, completely hollowfied. He then goes out to the lab where the rest of the Vizard are, sees them all hollowfied as well, and apologises to Tessai because his method didn't work. Then he goes outside to get some fresh air -- only to be stopped by the Second Division, who proceed to put him on trial in front of the Central 46, who blame Urahara for everything, banish him, place Tessai in jail, and plan on killing the Vizard. Thank God Yoruichi showed up when she did.
** It's even more Heartbreaking in the anime, with the poignant music and Urahara actually making it outside before being captured. Urahara is probably one of the biggest [[TheWoobie Woobies]] in the series.
* In the flashback, we see Nanao Ise as an oh-so-utterly-adorable child asking Shunsui about Lisa, who would read with her every month, holding a book about the size of her upper body. Lisa wasn't there, and Shunsui reassured Nanao that Lisa would come back safely from her mission. She didn't. To this day, Nanao frequently carries a very big book not unlike the one she carried as a child...
** Also during Nanao's and Shunsui's first appearance, Shunsui playfully says that he would never forgive himself is something were to happen to Nanao. This become HarsherInHindsight when its revealed that Shunsui suggested that Lisa be sent out to on the aforementioned mission instead of the officer was supposed to go.
[[/folder]]

[[folder: Fake Karakura Town Arc]]
* The deaths of Stark and Lilynette at the hands of the Kyoraku. The fact that his aspect of death was loneliness was never more apparent.
--> "I am not alone. I am not alone. ''I am not alone.''"
** Additionally, his dying flashback...
-->Lilynette: What will we do now?
-->Starrk: We can do anything.
-->Lilynette: OK, then where shall we go?
-->Starrk: Wherever...but let's stick together. Forever.
** His inner monologue while fighting Kyoraku is just as heart wrenching.
-->"Why do I have to fight with such a strong guy? I envied the weak ones. The souls of everyone in our group of friends wasted away and disappeared just from being around us. From loneliness we divided our soul in two. We don't know which was the original, or maybe it was neither of us. It's just that there was no other way to escape from the loneliness. I envied the weak ones. If you're weak, then you can gather in as large a group as you want. I want to become weak and if that's not possible, then I at least want to make friends that are as strong as me."
** Hearing him scream Lilynette's name over and over in desperation.
* Chapter 377. Aizen starts taunting the Vizard, trying to get them to attack, and [[BrattyHalfPint Hiyori]] falls for it. The result? Hiyori ends up in [[HalfTheManHeUsedToBe two separate pieces]], and in her last moments, apologizes to Shinji for disobeying him. Which in return dissolves Shinji into a screaming wreck, crying for Ichigo to bring [[TheMedic Orihime]] back from Hueco Mundo already. If you didn't feel sorry for Shinji before this chapter, it's pretty hard to now.
* In Chapter 387, Tousen's death. Sure, he wasn't [[TheScrappy the most popular of characters]], and he seemed like [[JerkAss a jerk]] in the more recent chapters, but in this chapter, we get flashbacks of him begging Central 46 to punish the man who killed his friend, and a shot of her grave, with him thinking "Why is it..." If that weren't enough, we then get Komamura and Hisagi standing over him, and despite the fact he ''tried to kill them less than five minutes ago'', they look more sad and hurt than angry. Komamura tells him he knew they would eventually have to fight each other, and says "I don't expect you to stop being angry. Nor will I tell you to stop hating. Just...don't focus only on revenge until you lose yourself...like when you lost your friend...my heart would be empty as well if I lost you." Tosen then thanks him, and tells Hisagi he wants to see more of his face, and "while I still can, I want to remember your face..." Then, he dies. [[LudicrousGibs Messily. He randomly explodes.]]
* '''CHAPTER. 392.''' It was pretty obvious that Aizen didn't die at the blades of Hitsugaya and co., but revealing that it was ''[[KillTheCutie HINAMORI]]'', of all people, that Toshiro ImpaledWithExtremePrejudice. Combine that, with Momo barely managing to ask him, "Shiro... chan... why...?", seeing Hitsugaya's subsequent reaction of utmost horror and the [[IronicHell maddening irony]] of Hitsugaya perhaps fatally harming the one person he has vowed to protect with his life...
** [[https://www.youtube.com/watch?v=UOEZyVdH2Ds The anime version]]. It's episode 293, just in case it's taken down and you need the number. The scene starts with Hitsugaya stabbing Aizen around 5:30, It gets worse for Momo around 6:45, and for extra tear jerker we have Hitsugaya holding the almost lethally injured Momo in his arms as he lays her down on a building's terrace, then screaming and going into a RoaringRampageOfRevenge to Aizen (who of course cuts him down) from 7:50 to almost the end.
** Hitsugaya's reaction is what really hits home. The fact that at first, he's horrified, but it doesn't quite compute. Like all that is running through his mind is "No way, no way, no way..." And then she asks WHY? And then ''snap'', it finally registers and he screams. This horrible, heartbreaking scream, that of course you can't hear because it's manga, but his ''face'' tells it all.
* Wonderweiss Margera's death at the [[BadassNormal bare]] hands of a depowered but still badass Yamamoto. [[AlasPoorVillain Who even expresses pity for the one he's just slain.]]
---> Yamamoto: Poor thing... Were your emotions taken away from you too? (Stares at Aizen) That was cruel from you.
* It’s minor, but Yumichika’s reaction to [[BestFriend Ikkaku’s]] defeat is heartbreaking. He attempts to rush to his aid, but is stopped by Kira and Hisagi. While Komamura does help with things and Ikkaku is fine in the end, it’s still distressing and a very real reaction.

[[/folder]]

[[folder: Deicide Arc]]
* 413: Seeing Chizuru in the border of an HeroicBSOD while telling Tatsuki and Co. how confused and upset she is. Whenever Chizuru acts like that -- it's kind of this reminder -- she's there for comic relief, but when the PluckyComicRelief is crying, all broken, that makes it way worse.
* Ch. 416: Gin’s apparent death, and [[AlasPoorVillain Rangiku’s reaction]]. His dying flashback makes it even worse.
** The flashback makes it ''even worse''. Seeing teen!Gin with the blood of [[KlingonPromotion the third seat he killed]] on his face and the guy's hakama as a cape, telling teen!Rangiku that he will become a Shinigami [[DeclarationOfProtection so she won't cry again]]... Now only it explains a lot about him (while NOT excusing his actions) but it also can't fail to bring the waterworks...
*** Since Gin presumably never told her, Rangiku had no idea why Gin was doing any of this (Betraying Soul Society, siding with Aizen, etc.). She didn't have a clue as to why Gin did anything he did.
** The TearJerker stands in 417, with Rangiku openly crying over his almost dead body. AND with his REAL last words, which basically means: "Yeah. Those are stronger eyes you've gained there. Now I can finally die and leave the rest to you".
* Chapter 420. Zangetsu's farewell to Ichigo. Zangetsu admits that he only ever wanted to protect Ichigo. They also know that once Ichigo uses the "Final Getsuga" he will be BroughtDownToNormal and they won't see each other ever again.
** And remember, this isn't just Zangetsu, this is Zangetsu merged with Ichigo's Hollow Side, who spent a lot of his screen time boasting about how he wanted to take over Ichigo's body. For him to admit that all he ever really wanted was to protect Ichigo, all the while starting to cry, makes it especially heartbreaking.
* Just the look on Ichigo's face in Chapter 421 as his flowers start to crumble away. His just looks so sad, because he knows that all his abilities, all his training, and Zangetsu are disappearing forever and he'll never get them back.
* Ichigo's CryForTheDevil moment in Chapter 422. Yeah, Aizen's evil, but hearing Ichigo wonder whether he secretly wanted to be "[[IJustWantToBeNormal just a shinigami]]" was just ''sad''. "[[LonelyAtTheTop In his blade...there was only solitude]]."
** From the same chapter, Yammy's Arrancar puppy goes to his dying master's side, trying to comfort him. It doesn't matter how big a jerk you are, your dog will still love you.
*** And then we get to [[http://athakra.livejournal.com/1789.html the third databook]], showing why Kokapurro (the Arrancar puppy) loves Yammy so much. That makes him even more {{woobie}}licious than he already was... We love you, puppy. We really do.
*** Gets even worse in the anime, Where you can here his barks, whines, and his mournful howl at the passing of Yammy.
* As of Chapter 423, it was revealed to us that Gin died, leaving nothing behind for Rangiku to remember him by. "You disappeared and didn't leave me a single memento. I've always hated that about you. But...if you had left something behind, then I probably would have never been able to move from that spot. You must have seen through that part of me. Thank you, Gin. I've always...liked that about you."
* Also from Chapter 423, Ichigo has lost all of his Shinigami powers and can no longer sense Rukia's presence, let alone see her. They say goodbye to each other as she slowly disappears from his sight. Oh, ''god''.....
** '' '''THAT.''' '' Realizing that even after everything he's suffered through, all the pain and agony, and all the good times too... They may continue on... but Ichigo is permanently handicapped from ever taking part in them again. A FateWorseThanDeath, indeed.
[[/folder]]

[[folder: Lost Substitute Shinigami Arc]]
* If the chapters in the manga are dark enough, the anime sets the mood perfectly with the opening theme, a kind of melancholy montage that shows that even though Ichigo's finally got a normal life, he's incredibly unhappy. It extends to the tone of the entire arc.
** [[https://www.youtube.com/watch?v=q3wnCuLRuJM The (first) ending theme]] is even more depressing to listen to. Kon is sitting on Ichigo's shelf, lifeless. Like an ordinary doll. Over piano music. Note how even though this arc takes place entirely in the World of the Living, ''Kon has no role in it and no character mentions him,'' implying this where he's been the whole time! Somehow seeing a memory fade away makes you forget how annoying he used to be!
* Chapter 424. There isn't any specific cause, but the aura of melancholy is ''palpable'', and you can tell that while Ichigo is putting on a facade of being perfectly satisfied, he's ''really, really'' unhappy.
** His facade breaks and the fact that he's probably crying inside the most when Keigo asks why Rukia hasn't come to visit. Ichigo's expression is just ''pained''.
*** Cue faux [[{{Tsundere}} Tsuntsun]] indifference from [[MenDontCry manly-front]] ''[[BlatantLies totally not]]'' {{emo}} [[BadLiar Ichigo]].
** And that "Ever since then, Rukia hasn't come to Karakura town even once."
* 425. Ichigo is now having recurring dreams about Rukia, Renji, and Byakuya.
* 427. When Karin decides she can't keep saying "IJustWantToBeNormal" and goes to Urahara's Shop to tell him she's willing to take up Ichigo's place. Not only it's quite the CharacterDevelopment for her, but to see her telling the people there that she doesn't want Ichigo to fight anymore, since he's sacrificed so much already and so he deserves a normal life and she wants to protect him.
* Chapter 453 is a mix of this and terror, as we see Ichigo's ''horrified'' reactions to having his friends (Keigo, Mizuiro, and specially Tatsuki) and family (Karin, Yuzu) taken away from him. They're still there, [[MoreThanMindControl but their minds have been totally messed by Tsukishima]], so they're totally... ''not'' there, mentally speaking.
* Chapter 456. For the first time since the series began, Ichigo actually questions why he wanted his powers.
** If that isn't bad enough... Tsukishima has manipulated/brainwashed Orihime and Chad into fighting Ichigo. He's basically forced into either a) harming his friends or b) losing the battle. Not to mention, there's the look on Orihime's face as they all fight; she's clearly heartbroken and reluctant on the whole deal. And the reason for that is because she legitimately believes the man she loves has gone ''insane'' and is trying to kill ''one of their best friends''.. BreakTheCutie or What?
*** The same goes just as much for Chad. "I didn't get stronger for this... I didn't get stronger to hurt you!" BAWL.
* 457. Ichigo's scream as Ginjo [[TakingTheBullet takes the sword for him]].
** 458. The ''look'' on Ichigo's face when Ginjo stabs him after revealing that he'd been working with Tsukishima the whole time.
* Chapter 459. For a moment, it looks like Ichigo's own ''father'' has just stabbed Ichigo. While it's quickly [[MoodWhiplash revealed]] to be [[HellYesMoment Rukia restoring Ichigo's Shinigami powers]], the look on Ichigo's face when he thinks his own father has also turned against him is just heart-wrenching.
** It's worse when you think about all the times we've seen Ichigo burst into tears throughout the series. Aside from flashbacks to when his mother died (and a really ambiguous scene at her graveside) this is the first time the audience has witnessed it, and the first time it's been explicitly stated. After all the horrible things he's been through, from having his friends kidnapped, failing at avenging his mothers' death, losing contact with all his Shinigami friends and having everybody important to him in the human realm (bar Ishida) brainwashed, he's finally just given up and broken down crying.
** If everything leading up Ichigo's breaking down and sobbing didn't smash your heart to tiny pieces, the fact the look on Uryuu's face is almost as desperate should. This panel is all Kubo needed to remind us that Uryuu and Ichigo are TrueCompanions, no matter what has happened.
* 462. Orihime starts having doubts and reacting against Tsukishima's MoreThanMindControl. Made worse by Tsukishima starting to re-brainwash her and Chad. Tsukishima, you (bleeeep)! Thank God for Urahara and Isshin stepping in before things go wrong again.
** Worse still is the exact ''details'' he starts replacing. He supplanted Orihime's brother and Chad's grandfather in their memories! That's just needlessly cruel.
* 466 gives us Jackie's AlasPoorVillain demise. Double since we get to see a glimpse of her past... as a crying teenage girl. That, and her last words ("I wish the one who saved me... was like you") imply a ''serious'' BreakTheCutie past and makes her a BrokenBird. ''Damn''. Nevermind that she ultimately lived through. Thank God.
* 468. When you look at it closely, Shishigawara declaring once and again his UndyingLoyalty to Tsukishima after having lost to Ikkaku is freaking ''depressing''. Whether it's sincere or {{brainwashing}} induced, it's sad to see a HotBlooded guy [[AntiVillain who seems to be a good person]] display such faithfulness towards someone who doesn't seem to care and is almost sure to actually ''discard'' him sooner or later. Even more so when Ikkaku [[WhatTheHellHero actually calls Shishi himself on it]], telling him to not throw his life away for someone who doesn't deserve it; even when Ikkaku is doing that in a very tough guy way, he has very good points, and it's clear that his words are affecting Shishigawara as well.
* 471. Fullbringers and their ''really'' fucked up backstories. The top moments are: Jackie finding her family dead and getting her boots dirty with her little brother's blood, Yukio being rejected by his dad since [[CuteMute he has a speech impediment]] and later turning more and more bitter, and Riruka naively using her powers on her first love [[LoveHurts and screwing it up]].
* And now there's 477. Where both Ginjo and Tsukishima ''finally'' show some bits of humanity, Riruka attempts to speak with Tsukishima and make him listen to her, and we also see how a Shinigami!Ginjou and a teenager!Tsukishima met, long ago.
* 478. There ''is'' a genuine tearjerker in the scene where Riruka wakes up in Urahara Shouten, is told by Ichigo and Rukia that the others Fullbringers are gone, ''and'' sees Orihime mourn for the Fullbringers. And then she starts crying too.
* 479. Riruka [[ButNowIMustGo leaves Karakura alone]]. Beautifully and heartbreakingly done.
--> Riruka: ''“Farewell, please forgive me. Because no matter how we say goodbye, I am sure that you will never… Never forget us.”''
[[/folder]]

[[folder:The Thousand-Year Blood War Arc]]
* 480: Even when we pretty much knew that Ichigo and the human TrueCompanions would save Yuki, seeing the poor kid's absolute and very understandable terror as the Hollows almost kill Shino and then gang up on him was really sad as well as so freaking scary.
* 483: Okay, so Chojiro Sasakibe wasn't exactly the better known character. It's still quite sad to see him thrown into a wall AND severely injured by the Vandereich, and later trying to relay info to Yamamoto while pretty much ''bleeding to almost death.''
* 485 is a chapter defined by MoodWhiplash as we have elements of TearJerker, SugarWiki/FunnyMoments, and horror rolled up and zigzagged. The sadness is provided by the confirmation of Sasakibe's death via a very shaken Yuki, Nel's despair as she begs Ichigo for help and the view of a captured Harribel.
* 486. Byakuya explaining to Renji what kind of person Sasakibe was, as well as Yamamoto mourning quietly for his lieutenant. Before the funerary pyre is lightened. '''Now''' is a damn shame that we didn't know more about the dude.
** It's also kind-of sad to see that Ishida, due to his Quincy duties, cannot join Ichigo and Co. to Hueco Mundo. It's a nice bit of CharacterDevelopment, as it shows that [[{{Tsundere}} no matter how he denies it sometimes, he ''does'' love and care for his TrueCompanions.]] And this being Manga/{{Bleach}}, it's followed by MoodWhiplash since he and Ichigo start [[VolleyingInsults verbally sniping at each other]] before Urahara comes to pick the kids up.
* 493. '''Ayon''', of all people, gets an AlasPoorVillain send-off.
* 494. Now now, who says that [[MemeticMutation NOBODY DIES IN BLEACH?]] Only a miracle can save Kira and, like, half the Third Division. If not ''the whole Seireitei''. [[TheWoobie Poor, POOR Kira]].
* 497. Hitsugaya calling out for Hyorinmaru and falling into despair when he doesn't reply.
** Also, Shino and the ''entire'' 13th squad outright having {{Heroic BSOD}}s as poor Hidetomo is slaughtered right in front of them, BreakTheCutie or what?
* 500 [[FromBadToWorse And the bad news keeps on coming]] because the Soul Society starts killing each other for some reason likely caused by the Vandenreich, and Ichigo is forced to listen to those screams of agony.
* 501. Not only Ichigo is still in a AndIMustScream deal as he can't break free and help those who need it, but this is followed by Byakuya not only being at the ''receiving'' end of a CurbStompBattle... but being pretty much MindRaped by As Nodt's combination of both MindRape methods via an horribly effective EmotionBomb. Who would say it at the start of Manga/{{Bleach}} but... ''poor'' Byakuya.
** Worse; He's about to be butchered to death by his own bankai. Considering the deep connections Captains have with their Zanpakuto, this is like having your best friend kidnapped and then forced to murder you. One can only imagine the complete mental breakdown Byakuya must be suffering right now...
*** The anime version of this scene really nails just how royally screwed Byakuya is, and makes his breakdown all the more tragic. Remember that Byakuya Kuchiki is a man who has committed himself for centuries to strengthening his mental fortitude, never once breaking his characterization as TheStoic. Then he not only has to watch his comrades suffer and die before his eyes, he has his Bankai stolen, his thoughts of Rukia are twisted and corrupted into something horrible because of the events currently happening around him, and his opponent's scathing, truthful words are eating away at him like insects crawling all over his body. Backed into a corner with ''no'' options left, Byakuya completely ''breaks'' and '''screams''' in despair as he futilely and frantically tries to land even a single hit on As Nodt, only to be skewered by his own stolen Bankai, Senbonzakura Kageyoshi.
* 502: Byakuya's last thoughts before either dying or collapsing... were asking Renji and Rukia to forgive him.
* 504: Chojiro and Yamamoto's past. Specially due to Yama's inner narrations.
* A small one in 505, when Yamamoto watches as Driscoll's body is burned to the very bone.
-->Yamamoto: "Choujiro, I can finally say my condolences... Farewell."
* 510: Royd Lloyd's happiness at being told he did well by Yhwach...who kills him on the spot. AlasPoorVillain to the core. This shows the real tragedy behind the Vanndereich Stern Ritter. Either all or many of them are actually normal Humans with latent Quincy potential drafted into the Vandenreich, are devoutly loyal to Yhwach but Yhwach has no qualms of killing his subordinates in cold blood. What Yamamoto said is true: the way he looks down on his men is wicked.
** Yama's [[OhCrap slow realization of how uterrly screwed he is]] and the Fanbase coming face to face with the fact, Soul Society is gonna lose.
* 511: It's the end, The Soul Society has fallen, The Vandenreich have won.
** Shunsui and Ukitake realizing that Yamamoto has died.
** Shunsui's anguished cry for Yamaji is met with him being gunned down like a dog.
** The Cover page of the chapter alone gives you the sign that things are going to turn bad.
** And to top it all off... [[GreyRainofDepression it's raining.]]
* 512: A dying Byakuya begging -- literally ''begging with tears down his face'' for Ichigo to protect Soul Society.
** Let's not forget Byakuya lamenting that Ichigo, as a human, was never meant to be on the Soul Society battlefield.
* 513: As Ichigo leaves to confront the Vandenreich, Byakuya drops his zanpakuto and it disintegrates.
* 515: The whole chapter. Squad 4 is so overwhelmed by the injured that they can't even bring back the dead, poor Isane [[TenderTears cries]] that she wished [[CombatMedic she could have helped in the battlefield]] even though she was ordered not to, [[HotBlooded Ikkaku]] is frantic at the possible loss of his captain, and both Rukia and Renji are in critical condition, with Renji still unconscious. The Captains meeting is less than optimistic with Yamamoto dead... Even [[NotSoStoic Sui-Feng is close to breaking down]] when [[GentleGiant Komamura]], Yamamoto's best friend, was trying to hold his anger in. Yeah, Soul Society has reached woobie-world status, [[CrapsackWorld and it's NOT pretty.]]
-->'''Isane''': "I'm an idiot. More than I... Unohana-taichou wanted to go out and help them... more than anyone...!"
-->'''Unohana''': "Do not shed tears, Isane-san. Just remember that the Fourth Division is to stay put no matter what. That was the order that the Captain-Commander has given us. ''His last order''."
** What pushes Sui-Feng to her limit? A report revealing that Byakuya and Kenpachi have escaped death, but may not ever wake up. Sui-Feng demands he stay back, protesting that she doesn't want to hear any more bad news in the wake of Yamamoto's death. Kensei calls her out, and Sui-Feng accuses him of being calm because he hated Yamamoto. This is what prompts Komamura to start shouting.
-->'''Komamura:''' Do you think you're the only one that wants to scream!?
* 523 Either Unohana or Zaraki [[ThereCanBeOnlyOne will die at the end of their training battle.]]
* 524 Knowing that one of them will die at the end of their training, both Unohana and Zaraki leave mementos for their lieutenants. Isane gets a letter, and Yachiru gets Zaraki's eye patch.
** Kenpachi admitting that he used to admire Unohana, and his ManlyTears when he realizes he was incapable of killing her...and that he's about to die.
* 526 Zaraki impales Unohana, apparently killing her. The saddest part? She's ''happy'' about this.
* 527: Kenpachi SCREAMING helplessly [[DiedInYourArmsTonight as Unohana dies in his arms.]] Seeing the [[BloodKnight badass warrior who revels in a good fight]], and had thus far shown no grasp of even the concept of regret or sorrow [[OOCIsSeriousBusiness nearly reduced to tears is sobering indeed.]]
-->'''Unohana:''' Farewell. You're the only man in the world...that could make me happy.
* 530: The conversation between a teenaged Ryuuken and Kanae Katagiri (the cute maid of the Ishida family) regarding his ill-fated ArrangedMarriage to Masaki is wibble-inducing. It's jarring to see [[TheStoic calm, collected]] Ryuuken openly admitting to misgivings as [[StepfordSmiler Masaki]] hides in her room clutching a pillow; Kanae tells Ryuuken that he's a very kind person, [[{{Tsundere}} but he denies it]], insisting that his concern isn't for their fate as a couple or as individuals but for the fate of the Quincy Clan as a whole. And that's when you realize [[TheDutifulSon Ryuuken's given up having any dreams of his own]] and the real wibbling begins.
* 533: The "Whitey" Hollow is killed, Isshin has been saved, Masaki is tending to him in a really cute manner. So why is the chapter here? Ryuuken and Kanae are watching the scene from afar until Ryuuken decides Masaki can handle things on her own. And the sadness in Kanae's eyes is simply ''heartbreaking''.
* 534: And we find out why: The injury from the hollow actually left something in Masaki that is now taking effect and is forming a hollow hole in her. If there was any reason Ryuuken acts as he is with Isshin, there was no doubt ''this'' was the event that triggered it.
* 535: Ryuuken's defeated expression when he realizes that Isshin and Masaki are soulmates both figuratively and literally. Not only will the experiment bind Isshin and Masaki for life, Isshin sacrificing everything without a moment's hesitation echoes Masaki defying the rules of the Quincy to save Isshin in the first place. Ryuuken just gives in when he sees that this Shinigami and complete stranger has more in common with Masaki than he ever will.
* 536: A [[HeroicBSOD devastated]] Ryuuken, under the GreyRainOfDepression, attempts to drift off into obscurity without ever going home again. It just reveals the enormous pressure he'd been under to redeem the Quincies' future, and how completely he believes he's failed because he couldn't save Masaki. And, if that wasn't sad enough, we then get to watch as Kanae's heart breaks for him.
* 537: Masaki ''was'' fully capable of defeating Grand Fisher -- but died because Yhwach stole her powers just as she was about to fight it. Poor Kanae was weak enough to die from the power drain alone... but not until she'd languished in a coma for three months. In a scene of wordless heartbreak, we see Ryuuken gazing out into the rain, accompanied by only [[TheLostLenore Kanae's photograph]]. ''Then'' it's revealed Uryuu has joined the Vandenreich. On the anniversary of his mother's collapse. It's not clear whether he even knows who killed her and how or whether Ryuuken knows where his son has gone, and suddenly the question is this: is Ryuuken thinking of his wife? Or his son? Or both? Heartbreaking chapter from start to finish.
* 541: If the fact that old man Zangetsu was trying to protect Ichigo from pain and suffering of being a Shinigami and thus was suppressing Ichigo's real potential doesn't qualify, then the look on Ichigo's face when he finds out certainly does.
* 545: Captain Commander Shunsui meets with Ichigo friends Tatsuki, Keigo and Mizuiro to discuss about Ichigo eventually parting ways with them...
* 546: Keigo doesn't take Kyoraku's words well. His reaction and the goofy face he makes have never looked less funny than they do. And when he grabs Kyoraku and yells at him a couple of pages later, it just makes it worse.
* 548: Of all people, '''Oomaeda''' manages to pull one. Guy's a big oaf and a ButtMonkey, but his DeclarationOfProtection to his baby sister Mareyo when she says "PleaseDontLeaveMe". [[FromBadToWorse And then BG9 steps in]]...
* 549: Omaeda tries his best against [=BG9=], but he's proven to be no match for the Quincy. The Quincy continues to interrogate him on Sui-Feng's whereabouts, and when he's not pleased with Omaeda's answers, he targets poor little Mareyo and ''stabs'' her all the while dangling her dying body right ''in front of him.'' Omaeda gets pissed [[BigBrotherInstinct enough]] and tries to pull a Byakuya on [=BG9=] but fails predictably. The look of utter helplessness and frustration at being unable to protect his little sister is heartbreaking. Luckily for him, [[BigDamnHeroes his captain comes back in the nick of time.]]
* 558 should be renamed as "The Chapter Where Sajin Komamura Finally Got ADayInTheLimelight And Totally Broke The Fandom's Hearts". Not only we see his last talk with the Leader, which is already totally heartwretching as they discuss their stands after their DuelToTheDeath, but then he ''completely loses all of his powers'', reverting to a wolf form where he's pretty much helpless. And he thinks about his last encounter with Tousen, where he told him that revenge was useless. And '''then''', his lieutenant comes for him... and [[YouAreNotAlone refuses to just leave Komamura there]], carrying him on his back and swearing to get back at Yhwach. Daaaaaamn.
* 573: When Kenpachi returned, Isane asked where Unohana was. When he told her he killed her, she just dropped to the ground, looking as if her world had just ended.
* 579: The look of pure desperation on Kenpachi's face when he finds that Yachiru is missing.
* 586: Ichigo, Orihime and Chad find out about Ishida's membership in the Vandenreich. ''Via seeing Ishida next to Yhwach, and then watching him willingly leave''. Especially a very bewildered and confused Ichigo just screaming away at him. It is truly heartbreaking. It doesn't help that Uryu ''immediately attacks'' Ichigo, and Orihime protecting Ichigo from Uryu. It just gets depressing to think about how these 4 were best of friends, and even had a really nice panel together fighting Hollows at the beginning of the Arc.
* 591: Aaaaand Hitsugaya's a zombie, having apparently died of his wounds where he collapsed.
** Gisele doesn't need to wait for a Soul Reaper to die to turn him into a zombie.
** Chapter 592 confirms he was alive when Giselle turned him into a zombie. [[FateWorseThanDeath Doesn't really make it much better though.]]
* 593: Not only are Ikkaku and Yumichika stressed about Hitsugaya's fate, but the latter also then proceeds to [[CurbStompBattle curb-stomp]] the two of them too.
** Not to mention Yumichika freaking out when Hitsugaya severely injures Ikkaku, making him ''nearly'' release Ruri'iro Kujaku, aka the one thing he wants to hide from Ikkaku, for his sake (only to be immediately curb-stomped too).
* 603: The palpable fear and sense of betrayal experienced by the Sternritter as their king kills and/or drains them for power to strengthen himself and revive his elites is just pitiful.
-->'''Liltotto:''' What's going on...your majesty...what...WHAT WERE WE TO YOU!?
* 614: After a mostly upbeat chapter start, the mood changes completely when Hiyori is told to put on her Shinigami clothes since the Vizards are properly joining the war effort. She protests, but Love gives her quite a short but scathing TheReasonYouSuckSpeech to shut her up. The sadness comes when she's almost ready with it, and there's a close-up to her completely dejected, saddened face...
* 616: Ukitake deploys what amounts to a mix of ThanatosGambit and HeroicSacrifice: using the "Kamikake" aka "Mimihagi-sama", the minor God that keeps him alive ever since [[DelicateAndSickly he was a child]], to try [[BarrierMaiden replacing the Spirit King]]. It's really hard to watch since the audience learns the circumstances that led him to be an ill boy, he's seen in ''intense'' physical pain/discomfort that includes truly epic quantities of BloodFromTheMouth and later [[BodyHorror gets MUCH worse]], poor Rukia understandably freaks out...
* 634: The climax of Bazz-B and Haschwalth's battle. Not only does Bazz fail to get any good hits on him despite pulling out the best of his techniques, but it ends with Bazz clutching his hand onto Haschwalth's coat as he bleeds out. Bazz collapses while Haschwalth turns his back and leaves. As Bazz blacks out, childhood memories flood his mind...
-->'''Bazz:''' [[MeaningfulEcho Let's become the strongest Quincies, Jugo.]]
* Poor Nemu's UndyingLoyalty getting her gorily exploded by Pernida when she tries to save Mayuri. Mayuri falls into despair and has a hallucination of Szayelaporro Granz calling him a hypocrite, that for all his talk about hating perfection, he considered Nemu to be his perfect creation. Mayuri comes out of his funk when he realizes this and decides to do what all scientists do when their experiments are destroyed: make improvements!
* 649-655: Shunsui's backstory. He had a poor relationship with his family and used to run away to seek shelter at the home of his brother and sister-in-law (Nanao's mother). But when his brother died from the Ise-family curse and Nanao's mother was forced to cut ties with Shunsui, later getting executed for passing a family treasure onto him as a parting gift, Shunsui lost the one place where he felt safe. He incorporated his brother's hairpins and sister-in-law's kimono into his attire [[TragicKeepsake out of grief]] and later adopted Nanao into the 8th Division, feeling guilty for his involvement in her mother's death.
** There is also the reveal in 649 and 650 that the love of Shunsui's life is his own zanpakuto, but the only way they will ever be together is in death. Thinking Nanao has died in his bankai, Shunsui is about to [[DeathSeeker take Katen's offer and "elope" with her]].
** Shunsui muses that there is a pattern in his life of people close to him dying in tragic or brutal ways and passing onto him some sort of responsibility.
* 681: As Haschwalth [[FaceDeathWithDignity calmly dies]] after losing to Ishida and being hit with ThePurge, there's a close-up to the hilt of his sword. [[TragicKeepsake It has his best friend Bazz-B's signature motif]].
* 685: Shunsui is seen [[TheAlcoholic drinking at and talking to what seems to just be a slab]], informing it (and the reader) what has happened to Soul Society in the 10-year timeskip. When Nanao calls him, the audience sees as he gets up [[DueToTheDead that the slab is a grave stone]], and he says "I'll be back. [[WhamLine We'll talk some more then... Ukitake."]] Over 10 years after he died in a [[SenselessSacrifice very noble but ultimately pointless sacrifice]] (though the few minutes he did buy Soul Society turned out, in the end, to be crucial, just not in the way he thought), and Shunsui is still grieving for his best friend, [[DrowningMySorrows drinking with him like times never changed]].
[[/folder]]


[[folder:Filler]]
* At Episode 262, [[TheWoobie Narunosuke]]'s death may not be as depressing as some of the other examples above, but considering that virtually the entire episode was spent developing his relationship with Haineko and his slow descent into a rage-filled berserker, and that Haineko [[TheTease herself]] actually had a crush on the guy, it's pretty sad nonetheless. Here's the kicker: Haineko's a mischievous catgirl with a knack for teasing and a flirtatious streak, close enough to qualify as a LovableSexManiac, so she's normally the one that makes other people blush. When it was ''her'' that blushed, over a much younger, blue-haired and shy {{Bishonen}}, no less, it was absolutely ''adorable''. Following that, however, for her to be sad, it's as rare as it is alarming and depressing, and many viewers apparently cried along with her as Narunosuke died.
** The episode where Kazeshini, Hisagi's zanpaktou, developed the "fatherly love" for that abandoned baby, and then took a beating for him, and left him, and... that was another super sad one.
* [[TemporaryLoveInterest Yoshino]] and [[{{Mon}} Goethe's]] deaths in the Bount arc, especially Goethe's last moments ("Mother..."), Yoshino [[GoOutWithASmile going out with a smile]], and [[HeroicBSOD Uryu's]] reaction.
* Episode 342. Just... all of it. Especially the end.
* In Episode 324, Kenpachi is about to die, having been supposedly defeated by his reigai. Yachiru sadly calls out, "Ken-chan!" and Kenpachi remembers his resolve to live. The music doesn't help things.
* Even if Nozomi was a pretty unpopular character, her death scene is still pretty tear-inducing, with a sad, yet still sweet goodbye.
* Muramasa. Throughout the arc, he comes across as a SmugSnake who lies about "freeing the Zanpakuto from oppressive masters", even though we've seen the bond between a lot of those swords and masters and know they're quite healthy. Then we figure out why he thinks that way: ''he's projecting''. Muramasa is a zanpakuto spirit himself. When Koga Kuchiki, his master, finally enters the scene, he's revealed to be an abusive dick. Everything Muramasa did was to reconnect with Koga, and gain his affection back, and even he knows it's doomed because Koga is [[BadBoss such a horrendous, vile asshole]] that it will never last even if he gets it.

[[/folder]]

[[folder:Movies]]
* The end of the first movie, ''Anime/BleachMemoriesOfNobody''. Senna sacrifices herself to stop reality breaking, and then Ichigo carries her back to the graveyard where here family plot supposedly is. Sadly, both she and Ichigo know that that family isn't hers. Because she's the Memory Rosary, all her memories are simply those of all the people she's made up of. Even so, she asks Ichigo if her name is on the gravestone, and [[LetThemDieHappy Ichigo tells her it is.]]
** Earlier, Senna had said she [[AnguishedDeclarationOfLove "couldn't live in a world without Ichigo."]] Well, here's the world WITH Ichigo...and she still [[HeroicSacrifice can't live in it.]]
* In the third movie, ''Anime/BleachFadeToBlack'', when Homura and Shizuku are freed of the hollow that was possessing them, named, and died. With Rukia breaking down in tears as she assists them in their last moments.
** And don't forget Byakuya's flashbacks to his past with Hisana.
** There's something both heartwarming and saddening when Byakuya returns to his manor for the first time in that movie, there's a montage of him searching every room in the building before he finally lands on presumably Rukia's designated room (with every other door in the house open). He can feel something important is missing but doesn't know what.
* [[Anime/BleachHellVerse Fourth movie]]. Ichigo's HeroicBSOD after the deaths of Renji, Ishida, Rukia... and specially '''Yuzu'''. Made worse when Orihime attempts to heal Yuzu but somehow there's a block on her powers and she cannot do anything, [[http://kokoro-beat.tumblr.com/post/16024184315 and Ichigo splinters]] '''badly'''.
[[/folder]]
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