* [[http://i22.mangareader.net/deadman-wonderland/16/deadman-wonderland-796119.jpg This page]] is just soul crushing, especially when you've read the previous chapters.
* Ganta's DespairEventHorizon in chapter 17.
** [[http://www.mangareader.net/666-33051-38/deadman-wonderland/chapter-17.html THIS GODDAMN FACE]].
* In his battle with Ichi and Hajime, Hitara appears to finally get some closure with his past. [[spoiler: Makes sense in a manga like this that a Tear Jerker would occur as two psychopathic thirty-year old "children" burn alive.]]
--> "Flame is beautiful. You were beautiful."
* [[spoiler:[[http://manga.animea.net/deadman-wonderland-chapter-39A-page-18.html Dammit, Shiro!]]]]
* The ending theme for the anime, showing the cast's happier times. Especially the slides of [[spoiler: Little Genkaku happily meditating under a waterfall, Nagi with his wife, and Seiji with his crew]].
* [[spoiler: When the twins tell Hagire, shortly after throwing themselves onto Senji's blades in order to protect him, that they love him. Hagire replies, "I never loved you." And they simply smiled, and said, "We know that, of course."]]
* [[spoiler: Shiro's backstory. '''All of it.''' Who knew that behind the sweet, bubbly facade lies a broken, scared girl who only wants to purge the monster inside her and experience freedom for the first time in her life?]]
--> [[spoiler:"It's alright if you've come to hate me, Ganta. I also... [[http://www.mangareader.net/deadman-wonderland/45/14 I really hate me."]]]]
* From the anime, Shiro breaking down in tears whilst eating cookies she was going to share with Ganta -- until he punched her in the face and told her to get lost after [[spoiler: she destroyed a data chip (spoiler: actually a bomb) that was a way of bringing Deadman Wonderland down in order to save his life]].
* Seeing [[spoiler: Warden Makina wheelchair-bound]] is really upsetting, considering what a badass she was.
* Remember Shiro being really excited about being able to ride the Ferris Wheel and Ganta saying he'd take her on it? [[spoiler: [[http://www.mangareader.net/deadman-wonderland/40/7 And then he found out who the Wretched Egg really was...]]]]
** [[spoiler:Ganta kept his promise in Chapter 54. [[http://www.mangareader.net/deadman-wonderland/54/34 Sort of]].]]
* Nagi's back story, and his sobbing meltdown in episode eleven had this troper bawling.
* For me, it had to be when you see Toto's [[spoiler: last moments as himself. Right before he loses his body, he shouts "I won't die, I won't! There's someone--"]]
** I think I'll take Toto's [[spoiler: [[http://www.mangareader.net/deadman-wonderland/53/20 actual final moments.]] It gets so much worse when you consider Hagire killed Yosuga using Toto's body just minutes earlier, when all she wanted was to be with '''her''' Toto again, granting her wish for them to die with each other in the worst possible way.]]
* [[WhamEpisode Chapter 55.]] Just when you thought [[spoiler:Shiro]]'s backstory couldn't possibly get any more tragic...
** Speaking of which, [[spoiler:Shiro]] reveals her wish to Ganta. What is it, you may ask? [[spoiler:Her wish is that Ganta, the only person Shiro ever loved and trusted completely, [[DeathSeeker would kill her since]] [[CannotSelfTerminate she can't kill herself in any other way.]]]] Dammit, I think I got something in my eye...
*** An entry from a fan-run Tumblr blog for [[spoiler:Shiro]] makes her wish incredibly worse. One fan is upset that [[spoiler:her wish is to die]] and asked her why she feels that her wish is the only solution. [[http://wretcheggandshiro.tumblr.com/post/50142516086/why-do-u-think-that-death-is-the-only-solution-for-u This is her response.]]
** The above, of course, sets up the FinalBattle [[spoiler:between two childhood friends and lovers. If that wasn't bad enough, remember that Shiro is a DeathSeeker and that Ganta's powers will ultimately kill him. The likelihood of either one, or both, of the characters coming out of this one alive looks... slim at best.]]
* The FinalBattle in Chapter 56: [[spoiler: Ganta vs. Shiro.]] You know it's gonna hurt when Minatsuki, [[BloodKnight of]] [[CuteAndPsycho all]] [[SociopathicHero characters]], is bawling too.
** The DarkReprise of the '[[SadBattleMusic Woodpecker Song]]' being recited on the pages where the fight happens makes it so much worse. Yes, they somehow managed to make that song even ''sadder'' in context.
* Chapter 56b, full stop. [[spoiler:Shiro resents not being able to live a proper life and feels ''incredibly'' guilty by all the havoc and destruction she causes. But, she doesn't want to go through her wish and states she wants to live after all with Ganta...]]
** Which is followed by a happy, if still tearjerking, moment when [[spoiler:Ganta writes his first name initial in Shiro's right hand and offers to be with her for the rest of her life. [[HeartwarmingMoments She accepts.]]]]
*** [[spoiler: And then their Branches of Sin react, triggering an explosion that engulfs the two.]] Talk about one hell of a sobering {{Cliffhanger}}.
* There's a flashback were Shiro is trying to share her pudding with Aceman action figure that was so simple and so desolately lonely, especially when she admits to herself that Aceman can't eat with her and the tears come. (both from Shiro and this troper)