* Just about everything in the second episode of the first OVA.
** Screw that, the ''whole'' first OVA series is a big TearJerker. And the original manga/TV series had its moments as well.
* The first TV episode. Kenshin has had enough pretending not to be the Battousai, and shows for the first time why he has such a strange philosophy to fighting:
--> '''Kenshin:''' "A sword is a weapon. The art of swordsmanship is learning how to kill. That is the truth. What Miss Kaoru says is sweet and innocent talk that only those whose hands have never been stained with the blood of men can believe. But to tell you the truth, I much prefer Miss Kaoru's sweet and innocent talk over the truth, that I do."
* The funeral for [[spoiler:Kaoru]] who [[DisneyDeath wasn't really dead at the time]] but, hey, we didn't know that!
* Don't tell me you didn't die a little inside when Misao entered the place where [[spoiler:Okina and Aoshi]] fought just in time to see [[spoiler:her beloved Jiya]] [[DisneyDeath collapse]] before her eyes.
* [[http://www.youtube.com/watch?v=bzeeNAH2ckY "Towa no Mirai"]], the ending theme for TheMovie, ''Ishinshishi e no Requiem'', tends to do this to a lot of people.
** As for TheMovie itself? There are several: [[spoiler: Gentatsu's last moments and Shigure's reaction, Shigure's goodbye to Toki, Yahiko's huge HeroicBSOD when he finds his BigBrotherMentor Musashino's lifeless body among those of Shigure's followers, and especially Shigure's death in Kenshin's arms]].
* Say what you want about ''[[BrokenBase Seisouhen]]'', but admit it. You cried at least once during either episode.
** [[spoiler:Kenshin and Kaoru die]]. Of course, if you read the original manga you just might be pissed instead, because the manga's ending is HappilyEverAfter. (But hey, according to Watsuki, it's CanonDiscontinuity. Let's breathe in and say thanks).
** The OVA ''did'' have genuinely sad moments, like [[spoiler:the last time Kaoru and Kenshin make love before he leaves and share a very sad pillow talk, Megumi trying to urge the deathly ill Kaoru to live a bit more so she can see Kenshin a last time, or Sanosuke doing the same to an amnesiac Kenshin in China]].
* Soujirou's steady breakdown during his fight with Kenshin is so heartbreaking.
** One can't help but tear up when he pleads with Kenshin: "If you claim to protect the weak, then ''where'' were you when I needed you?!"
** To elaborate, Soujirou underwent [[spoiler: major abuse at the hands of his family due to being the bastard child of his father and his mother (who was his mistress). He also endured their scathing remarks about him being a bastard child and we learn that he was only allowed in the family for appearances sake. It isn't until Shishio turns up badly wounded that Soujirou eventually becomes his disciple and kills his entire family, resulting in a HeroicBSOD that he didn't realize had, until his fight with Kenshin]]. It really puts some perspective on that kinda stuff.
* Kenshin's farewell to Kaoru before he goes after Shishio. No wonder poor Kaoru got depressed (if perhaps [[{{Wangst}} excessively so]]) after that.
** Surpassed by Kenshin's backstory from the Rememberance arc (animated as the ''Tsuiokuhen''/''Trust and Betrayal'' OVA) in which Kenshin [[spoiler:accidentally kills his wife Tomoe after being temporarily blinded, by a group of ninjas. She was trying to help him and to not lose her second chance at happiness, and then SLASH]]. The shock of this causes Kenshin to swear to never kill again, and [[spoiler: Tomoe's brother Enishi to swear revenge and to turn Kenshin's life into a living hell]].
** In the series, there is also [[spoiler:Yumi's death in Shishio's arms after he fatally stabs her with his own katana and then comforts her as she passes away, and Kenshin's first visit to Tomoe's grave in years]]. Both of them with the ''Adagio Cantabile'' of [[{{LudwigVanBeethoven}} Beethoven's]] ''Pathetique Sonata'' as background music.
** The manga scene where [[spoiler:Kenshin finds Kaoru's (supposed) corpse and [[HeroicBSOD completely breaks down]] as he believes Enishi has finally gotten his revenge on him]].
* The end of the first ''Tsukiokuhen'' OVA, depicting how Kenshin and [[spoiler:Tomoe]] met.
** And [[spoiler:Sayo]]'s death. God, poor [[spoiler:Sayo]]. The Shimabara arc was the last good part of the anime, and despite having a BittersweetEnding, [[spoiler:Sayo's fate]] remains a TearJerker.
*** It's especially bad in regards to [[spoiler: the death scene itself. Sayo lays fatally wounded in the arms of her friend ([[ImpliedLoveinterest or more]]) Sanosuke as he's apologizing for not having been able to shield her... and then he realizes that ''he doesn't even know her name''! (He only knows her as Magdaria, her Christian name). He tearfully points it out, then Sayo calmly looks at him and whispers [[FamousLastWords "Sayo... my name is Sayo... Sanosuke, I'm glad I met you..."]] and [[KillTheCutie perishes almost]] [[TooGoodForThisSinfulEarth immediately afterwards]]. The next seconds show [[HeroicBSOD the emotionally crushed]] Sanosuke [[DiedInYourArmsTonight cradling her lifeless body]], whispering "Sayo... I'm sorry, Sayo..."]]
*** The flashback where [[spoiler:Shogo and Sayo watch their father die fighting the Shogun's forces, then told by their mortally-sick mother to leave her and "become strong as iron", shortly afterwards seeing her shot dead on the beach, and ''then'' sailing away with their uncle... past the crucified bodies of everyone in their village]]. And then [[spoiler:young Shogo]] made an oath to become "as strong as God!" and the source of his messianic complex was made painfully obvious.
* When [[spoiler:the Oniwabanshuu died protecting their leader]]. And God, the look on Aoshi's ''face''...!
** Another Aoshi-related one: [[spoiler:When Okina openly asks Kenshin to [[ShootTheDog kill Aoshi]] since he believes he's [[JumpingOffTheSlipperySlope gone beyond any chance of redemption]].]] Seeing [[spoiler:Misao]]'s absolute ''[[HeroicBSOD heartbreak]]'' at that makes it even ''worse''. Poor, poor child.
* [[spoiler:Anji Yukyuzan]]'s horribly depressing backstory. My God, [[spoiler:Anji's screams of fury and pain when he sees the shrine burned down and his stepchildren dead, especially the teenage girl with a PrecociousCrush on him]]... it ''never'' fails to bring the water works for me.
** Even more when either [[spoiler:Anji uses the ashes he pulls from Tsubaki's corpse's burned hands to paint on his own face, with a look of pure '''hatred''' in his eyes]] or when [[spoiler:Sanosuke [[WarriorTherapist calls out]] [[IKnowYouAreInThereSomewhereFight to Anji]] ([[WhatTheHellHero "Don't you see these kids crying over the blood you've spilled?!"]]), then he [[MyGodWhatHaveIDone realizes how far gone he has been for years]], sees the spirits of Tsubaki and the kids reminding him of his true purpose in life... and is defeated.]] Waaaah!
** The PocketProtector that saves him from Sanosuke's first successful blow... is a memorial tablet dedicated to them. He's been carrying it all these years.
* Iwasaki Taku's heartbreakingly gentle and heartfelt musical score for the ending of ''Rurouni Kenshin: Memories''.
** Hell his score for ''all'' of the OVA's counts as this.
* One of the last images from the ''Trust and Betrayal'' OVA: Kenshin sits under a tree during a storm [[CradleOfLoneliness clutching the shawl]] of [[spoiler:Tomoe, who recently died]]. As he does that, [[spoiler:Tomoe's ghost wraps her arms around him to try to comfort him]].
* The scene between Enishi and Geezer at the end of the Revenge arc. [[spoiler: Enishi, after being defeated by Kenshin and left emotionally broken, ends up in the same village Kenshin went to after he (Kenshin) was left emotionally broken by the thought that Kaoru had died by Enishi's hands, and with the same broken look Kenshin had while sitting there. Then, he meets with Geezer, who is heavily implied to be his and Tomoe's father, but they only remember each other from when Enishi was a little kid. The two end up talking about how they "remember each other from a distant past", but without revealing their names or anything that could tell each other that they were indeed son and father. However, it's Geezer words that make it all the more special, with the old man saying that Enishi's place was not there, that he, like Kenshin, would one day recover and continue to live on, but that he should just rest in the meanwhile]].
* Kiyosato Akira. All he wanted to do was build a name for himself and become a man worthy of his fiancee. Unfortunately the samurai he is guarding [[spoiler: is targeted by Kenshin. The entire time during his very short duel with Kenshin he is frantically thinking "I don't want to die! I can't die here!" but he can't back down from the fight and ends up dying senselessly. The senseless part is more apparent in the first OVA, when the very samurai he is guarding actually ''shields him'' from a fatal blow while screaming "You can't die here!".]]

!![[Film/RurouniKenshin The 2012 Live-action Film]]
* All of the flashbacks showing Kenshin during his time as Battousai. It's a testament to Takeru Sato's acting that, despite him technically playing someone (Kenshin-as-Battosai) 7-9 years younger than himself (Sato himself is 23, Kenshin began killing people at age 14), he was able to portray a young man who can effortlessly kill yet is beginning to be [[TheseHandsHaveKilled crushed by the weight]] [[MyGodWhatHaveIDone of his crimes]], however [[WellIntentionedExtremist well-meaning they might be]].
** [[spoiler: Kiyosato Akira]], [[HeroicSecondWind getting back on his feet]] even as Kenshin carves him up, screaming and gurgling about [[ThePowerOfLove someone important to him]]. Even when he fell for the last time, he simply [[{{Determinator}} refused to die]], whispering it over and over and crawling across the ground, until he is given the coup de grāce. The next day, we're shown his fiancee, [[spoiler: most definitely Tomoe]], breaking down in front of his blood and rain-soaked corpse.
** This flashback itself was triggered by [[spoiler: Kenshin seeing the corpses of dead policemen Jin-e rampaged against in his outings as the fake Battousai]], ending with Kenshin's self-reproach (which shows how [[SurvivorGuilt unresolved his issues with his past are as of yet]]):
---> '''Kenshin:''' ''"You are still a killer."''
** Saito's subdued yet-no-less icy reproach to Kenshin [[spoiler: after looking on at the aforementioned dead cops, strewn together with the thugs Kenshin knocked out in Kaoru's dojo earlier in the film]], just shows how much he [[spoiler: [[AFatherToHisMen actually cares for his colleagues and subordinates]].]]
---> '''Saito:''' ''"If you killed just one of them, [[spoiler: my policemen would still be alive]]."''
* Speaking of Saito: He never shows it, but the words he consistently repeats to Kenshin (from the prologue at the Battle of Toba-Fushimi and at his last scene) betrays a man embittered by the years, yet still animated by his own code of justice to push on even in a world he doesn't appreciate:
--> '''Saito:''' ''"Live by the sword, die by the sword. There's no other path for us."''
* The aftermath of the Battle of Toba-Fushimi itself in the prologue counts as one. When you read history books about the Meiji Restoration and the struggles it had, one might find it exhilarating and even exciting. Seeing the dead bodies of all combatants, friend and foe piled up together in the field [[SnowMeansDeath while being slowly buried in snow]], drives home [[WarIsHell how many lives and personal futures have been sacrificed just to bring a new era]]. It's a fitting counterpart to the fiery demise of Lord Hidetora's castles and retainers in Creator/AkiraKurosawa's ''Film/{{Ran}}''.
* Kenshin ruminating over the agony of the innocent civilians who were poisoned by Kanryu, and realizes it is his inaction that caused their suffering; this finally drives him to bring the drug-dealer to justice.
* However odd this might sound, considering the backdrop above, we can find [[spoiler: Jin-e's life to be one the more you think about his background in this film. While he has always been thought of as a bloodthirsty bastard in the manga/anime, the film supposedly shows him to us in the prologue as someone who has been warped by the violence of the past era, who perpetuates his violent way of life because it's the only thing he knows]]. His use of the name ''"Battousai"'', in a way, becomes comprehensible, [[spoiler: if all the more tragic. He could have been what Kenshin have become had he not learned the value of people around him]].

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