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3For a gag series, ''Gintama'' surprisingly has many moments that are bound to make readers cry waterfalls. '''Beware of unmarked spoilers.'''
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5* Gin's speech about "carrying a heavy weight on a long journey" in Chapter 13, with the heavy weight referring to his comrades (both the Joui 4 during the war and the newly-formed Yorozuya trio in the present), can definitely induce ManlyTears.
6* Episode 17 which introduces Gengai and focuses on his backstory with his deceased son Saburo whom his robot is based on. During the Festival the robot doesn't respond and gets damaged by Gintoki, but doesn't attack him. He then says that he ''loved'' Gengai as the father he knew, despite problems they had in the past, implying that Saburo's soul was in the robot Gengai created.
7* Early on in the series, Sougo asks the Yorozuya to investigate the illegal underground fighting ring. The top fighter turns out to be a kindhearted father to orphaned children who wants to try and start a new life. Just as he sets out to escape Edo and start over, the Tendoshu (who are behind the ring) have him killed. The following scenes with his last words and the children tearfully asking Gintoki to help them in exchange for their treasures (read children's trinkets) is touching in a heartwrending way.
8* The Amenesia Arc (episodes 31-32). Gintoki gets amnesia from a traffic accident, and any attempt to help him fails. The Yorozuya house is later destroyed by an incoming spaceship (courtesy of Sakamoto), with Gintoki claiming it's impossible for a human to stop it. Gintoki then tells Shinpachi and Kagura, more or less, "The Gintoki you knew isn't here anymore", and then leaves. Thankfully, he regains his memories in the end.
9* Umibozu arc (episode 40-42) has Umibozu, Kagura's father, coming to take her back.
10** Kagura's background is revealed: She was born into a poor and dysfunctional family. Her father rarely came home, her mother was sick and dying, and her brother was a blood-thirsty fighter. One day, her brother attempted to kill their father to test his strength. The fight went out of control, father lost an arm and brother was almost killed. After that her brother left, her father stopped coming home in fear that he would one day destroy their family, and her mother died from illness. Little Kagura was left growing up in an empty house waiting for her to return, until she had enough and ran away to Earth.
11*** Even more depressing when you realize this is why Kagura could wait for Gintoki that long in Amnesia arc... she is used to waiting for someone who never returns.
12** Gintoki's initial dismissive reaction was frustrating to watch. However it was revealed at the end that he never had a family and so thought Kagura was better off living with her real father than with someone like him.
13* The Inugami Arc focuses on the Yorozuya and the Priestess Sisters trying to save Sadaharu, who's turned into his demon form and has gone out of control. The Yorozuya in particular are incredibly stressed when he first transforms and try desperately to stop him from wrecking havoc but are also scared of hurting him (as seen with Gintoki who can't bring himself to land a blow on him at first because all he can see is the usual happy-go Sadaharu and not the demon he's become).
14* Tama's HeroicSacrifice at the end of her introduction arc. It made it worse since she forgets who she is, at least initially.
15* Episode 73 focuses on a man and a bear cub he raised, only for him to be forced to kill it later when it becomes infected by a disease and goes rampaging in a mad fit.
16* Kyuubei's backstory in the Yagyuu arc reveals they lost their eye trying to save Otae (who was attempting to defend Shinpachi at the time) from debt collectors as an adolescent. A guilt-ridden Otae promised to become their new left eye, which is what kickstarts the arc.
17* Okita Mitsuba Arc:
18** Hijikata rejecting a heartbroken Mitsuba before the Shinsengumi left for Edo, and the real reason behind why he did it: he didn't want the woman he loves to be unhappy with him, as his dangerous occupation was bound to bring her sadness. He preferred she went and found happiness with another man than himself, despite his own feelings for her.
19** Mitsuba's death, with the normally sadistic {{Jerkass}} Sougo beside her bed. He desperately clutches her hand and holds it to his cheek as she dies, showing for the first time a totally heartbroken Sougo taking the hand of his sister.
20** Hijikata's reaction to Mitsuba dying? Eating her favorite food (which he was meant to give to her but chickened out), ''while sobbing'' and [[SandInMyEyes pretending it's because the food is too spicy]].
21* Ito's death at the end of Shinsengumi Rebellion Arc. Considering his past and how alone he felt, only to find that he wasn't alone when he entered to the Shinsengumi is totally heartbreaking.
22* At the end of episode 108, a short story about an orphan, Kyojiro, taken in by a group of Yakuza, he dies by the grave of the leader who he considered a father, believing until just before the end that he had failed to protect the people important to him. Of course, as soon as Gin manages to convince him otherwise, he is fatally shot.
23* Chapter 175/Episode 115 of the Ryugujo Arc: even though Shinpachi's' '' actually dreaming'', his TragicDream consists of him being stranded on an island for ''60 years'' while being reduced into a weak old man until he was saved by the rescue team. During the interview, he told the reporters & the audiences that he need to find the rest of the Yorozuya members, only to find out that the place that is once his office has become a Lingerie pub, and he eventually claims that he's "Alone in the world" after he unsuccessfully looks for Gintoki and Kagura anywhere on the crowd.
24* Seemingly subverted then played straight in episode 130. It starts out seeming like a slice of life story about an old dog and old man loyally dying at the same time, except the dog turns out to be an alien that eats planets and the old man was rude and told people to go die all the time. It's played straight in the end when it turns out that both don't want to die before the other because they don't want to make the other sad by leaving them alone and competing with each other while telling the other to die in the only way they can really show affection to each other. The old man dies as soon as he sees his last friend, the dog, die first after their race (while both are dying) so that he won't be left alone.
25* Yoshiwara in Flames arc:
26** Yosiwara as a whole is a dark place: An underground red-light district where politicians go to indulge themselves and discuss national secrets. Women there are either kidnapped or sold into prostitution, and they can never leave the place or go to the surface because they already overheard too many secrets. Whoever tried to escape to the surface will be killed. Pregant women will be forced to abort and women too old to keep serving will also be killed. A life of despair.
27** Kagura and Shinpachi's fight with Abuto is awfully one-sided at first, with the older Yato clearly having the upper hand. He's particularly brutal at one point and keeps hitting Shinpachi in the stomach so harshly that blood (amongst ''other'' fluids) is pouring out of his mouth and nose, and Kagura screeches at him to stop. This is what triggers Kagura's Yato blood to kick in and have her curb-stomp Abuto, which terrifies Shinpachi so much he has to hold her off from killing Abuto and becoming the monster she shouldn't be.
28** Seita finally reunites with his mother Hinowa (who's revealed to be non-blood-related, but he doesn't care) and wants to help her escape. The problem? The ArcVillain Housen had cut her tendons on her ankles after he caught her trying to escape in the past, meaning she's unable to walk with her own two feet (and thus leaving her unable to leave the room Housen had her in).
29* The Red Spider arc:
30** The ArcVillain Jiraia's backstory as Danzo Tobita, which involves a little sister that went and killed herself after being horrified by what her brother's become. Zenzou reveals all of Jiraia's villainous acts was a part of a plan to get his student Tsukuyo to eventually kill him as his punishment. He succeeds, but he spends his last few moments with Tsukuyo by his side as they find peace. Afterward, Tsukuyo is visibly saddened by her former mentor's death even though she refuses to admit it.
31** YouAreNotAlone is ultimately the subplot for Tsukuyo in this arc. After her mentor's supposed death years ago, she taught herself to be independent and to not rely on others. It takes a lot of meddling and words of comfort from the Yorozuya to convince her that, no, she really isn't alone and she shouldn't feel shame in getting help from her friends.
32* Despite the hilarity and absurdity of the Timeskip Arc, what's saddening for Shinpachi and Hijikata is that they spent some time on vacation and came back to find their world and their friends so changed that they felt they had no place in it anymore yet had no choice but to put up with it all as they had nowhere else to go.
33* The Four Devas Arc:
34** One of the first horrifying moments of the arc is Otose's [[DisneyDeath supposed death]] at the hands of Jirocho in front of her husband's grave. The moments leading up to the end were terrible too. Otose gets Kagura, Shinpachi, Tama, and Catherine out of harm's way by telling them she's taking them out to eat. She tells them to go ahead before [[FaceDeathWithDignity turning around to go to the graveyard and meet Jirocho]].
35--->'''Otose:''' I have a favor to ask. They call me one of the Four Devas, but I don't have any members in my faction. My life is all you need. They serve no use at all. [[TrueCompanions They just happen to be my family.]]
36** Five minutes later, we see Gintoki desperately trying to get to Otose in time--[[YouAreTooLate but it seems he doesn't.]] Cue Gintoki unleashing his rage on Jirocho, only for him to lose and crawl desperately towards the dying Otose, accompanied by flashbacks of their first meeting and his promise to protect her.
37--->'''Jirocho:''' Get lost, watchdog. There's nothing for you to protect here.
38** The aftermath of Otose’s attack is one of the darkest hours of the Yorozuya, with each member doing a OOCIsSeriousBusiness moment: Gintoki has hit a DespairEventHorizon and decides to leave, the normally cheery Kagura bursts into tears, and the OnlySaneMan Shinpachi punches Gintoki in a fit of rage to make him stay.
39* At the end of episode 226, when the old prisoner revealed that he knew the letters he was receiving were all written by the prison warden, for his "nasty but dedicated son."
40* The end of the Renho Arc, which is filled to the brim with about as many shout-outs and parodies as ever, takes a sharp turn hard enough to induce severe MoodWhiplash and seemingly ends in one of these when Elizabeth left the series for good. (It is then subverted in the most trolltastic fashion when the cast is giving Elizabeth a grand send-off... and gets greeted by the ''real'' Elizabeth, who was away on vacation. Katsura forgot to mention the Elizabeth they tried so hard to find and say good-bye to was only the Monday Elizabeth.)
41* The Kintama Arc:
42** Our protagonist sudden returns to the Yorozuya after a drinking night, and he goes and salute their comrades, he finds out that he has been replaced by someone who is better than him, and the guys he thought to be his friends don’t EVEN remember him. It's not a joke. They aren’t the only ones to have forgotten his own existence. And he just wants to beat the hell out of him to know a reason of why everyone forgot about him and he is just... there, taking the credit of everything he has done (over the past 40+ volumes/250+ episodes) but those who were his friends tell him that he is nuts, and that he just have to keep out of Kabukicho. Just dammit, seeing his face as Shinpachi and Kagura tell him that he ''can't'' be acting that friendly on them is heartbreaking. Going downhill from there, Kintoki convinces Gin that everything he lived is a lie, making him doubt everything.
43** After losing all hope of his own existence, Sadaharu and Tama comes to his rescue, and the robot maid tells him that he doesn't really have to lose his own light because it's what is differs him with Kintoki... and that he is the only one that must try to recover the memories of him with his friends.
44* The Courtesan of a Nation arc:
45** The 2 seconds still image of how Gintoki, Katsura, and Takasugi were left with their beloved teacher's head after the Bakufu executed him is truly riveting. After that still image, it's truly a miracle that Gintoki and Katsura end up relatively sane after the war in comparison to Takasugi, who's gone on a world-ending rampage.
46** The flashback of Gintoki's teacher and adoptive father Shouyou being taken away from him, and how he tries to calm Gintoki by telling him that he'll be back very soon... while also asking him to promise to protect all their friends while he's gone. Made even worse when you realize that most serious arcs, all the times we have seen Gintoki risk his life for someone, especially when we didn't understand why he did it when it was just some random kid he didn't know anything about or the old courtesan in this very arc... it's because of the simple fact that ''he never comes back.''
47** Maizo and Suzuran's tragic love story in general, but the end of the arc deserves special mention. They're finally reunited after so many years of being apart, only for Suzuran to die and leave him ''just as they meet again''. It's not all bad, as Maizou's spirit seems to carry Suzuran in his arms into the afterlife, but it's still one hell of a tear jerker.
48* The Beam Sword Style Arc stars the "return" of Shinpachi and Tae's big brother figure Hajime Obi, who had gone missing and was assumed dead. Their joy of having him back is short-lived as it turns out Hajime got taken by the enemy, is being taken over by his evil alter-ego and came back to destroy Earth. Hajime gets back his posession of his body during his fight with Shinpachi and eventually sacrifices himself to save the planet. This incident proves to be one of the Shimura siblings' most painful experiences.
49* Kondo's flashback arc with his teacher. It's a short, touching arc, especially this line: "These sure are some warm handcuffs..."
50* Tama is able to become friends with machines. One such example is when she befriends a malfunctioning cigars' vending machine from a local shop that was going to be shut down soon. She spends all the chapter talking to it, reassuring it would be fine even if the shop was going to close. The shop closes, it gets torn down and Tama still gave it some refuge... until the moment it is retired and thrown to a local litter... and it finally gives it up. ''She'' is still there, protecting it from the rain, no matter how things ended up and the rain makes it look like she was ''crying'' too.
51* The Shogun Assassination arc:
52** Takasugi's backstory revealed that '''[[TheHero Gintoki]]''' was the one to kill Shouyou. At that time everyone but Gintoki was captured, and the only choice was either to kill Shouyou or kill Takasugi and Katsura, who were being held hostage. Remembering his promise to Shouyou to protect his friends, Gintoki ultimately decided to kill his teacher despite Takasugi begging him not to. After Gintoki decapitated Shouyou, an enraged Takasugi threw himself at Gintoki, only to get stabbed in the eye by Oboro. The last thing Takasugi saw with his left eye was Gintoki's crying face.
53** Takasugi and Gintoki hated each other because they were one and the same. Takasugi knew if he was in Gintoki's place he would have chosen to obey Shouyou and kill his teacher, while Gintoki knew if he was in Takasugi's place he would have wanted to destroy the world that took Shouyou away. By trying to kill each other, the two were metaphorically committing suicide - both cursed themselves for being weak and unable to protect their teacher and comrades. This was hinted back from Courtesan of a Nation arc.
54--> One was trying to protect Shoyo’s legacy. The other was trying to destroy Shoyo’s legacy. But they had one thing in common. They both had such sorrow in their eyes.
55** Chapter 524 ends the Shogun Assassination Arc with a heart-breaking surprise. Despite everyone's efforts to protect the Shogun as he and his sister go into hiding, two weeks later he gets hit by a poisoned needle. He spends his last moments with his sister (who ''doesn't know he is dying'') and resting his head on her lap. In other words, the freaking Shogun... is ''gone''. The anime adaptation decides to twist the knife further by having the scene play out as the credits start to roll. The entire time the credits are rolling Soyo is lovingly petting the Shogun as he's resting his head on her lap. Unbeknownst to her, he's already passed on.
56* The BarberShop arc. One of the funniest, but still with its sad bits:
57** Kondo comes looking for a barbershop so that he can get a makeover, because his current image is attracting too much criticism from Otae, and each barbershop rejects him. He's in such a pitiful state that even the Yorozuya can't mock him, and instead pretend to be barbers to accommodate him.
58** The Shogun's fate is hilarious to us, but not to him. Getting his chonmage cut, his face stretched out, golden retriever poop on his head... he's in absolute tears.
59* Farewell Shinsengumi arc:
60** The funeral for Shigeshige marches through Edo, with Soyo and Maizo walking alongside with depressed looks. Shinpachi and Kagura watches on with sadness, and Gintoki limps around on his crutches with EmptyEyes. Meanwhile, Zenzo thinks about how all his efforts to save him have been in vain.
61** Nobunobu orders Matsudaira and Kondo arrested and sentenced to death for failing to prevent Shigeshige's murder. Having predicted this, Kondo sends the Shinsengumi as guards for the march beforehand, preventing them from risking their lives to stop his arrest. They come back in time just to see him arrested, leaving Okita and Hijikata shocked. With the Shinsengumi disbanded and the Shogun dead, the Shinsengumi roam around endlessly without purpose or plan.
62** For all the grief he gives her with his antics, Otae is sad about the news of Kondo's arrest and eventual execution, and stands up tearfully to Nobunobu while praising her usually annoying stalker.
63** Things get even sadder with the reveal of Isaburo's backstory, which add a dark twist to his e-mail obsession. His pregnant wife forced him to use a phone so they could communicate while she delivered the baby and he spent much time and effort coming up with a name for their child. When he finally comes up with a name, he finds both his wife and newborn killed murdered by the Naraku. Twisting the knife further, it is revealed he was going to name her ''Nobume'', which he gives to supposedly responsible Mukoro (who is truly innocent), pretty much proving they have an adoptive father-daughter relationship.
64** The revelation that the BigBad Utsuro is actually Shouyo (sort of), when his mask finally comes off. It's downright shocking to see Gintoki stare in awe and confusion as he sees a man who looks exactly like his teacher and father figure fight him. The smile he gives to Gin after this reveal is almost a punch to the gut, as it's the same kind of heartwarming smiles he used to give him as his teacher.
65** Kondo briefly fakes his death when Isaburo throws Katsura's "suspended animation" pill in his mouth to make him unconscious and slashes his face to make it look like he killed him. Although this moment doesn't last long, the Shinsengumi and their allies are ''horrified'' when they find him presumably dead. They nearly go into a HeroicBSOD before Gintoki ruses them to keep fighting.
66** Right as they're all about to escape the island, Isaburo uses his own body to protect Nobume and his previously scorned half-brother from a bunch of half-dead Naraku, but falls to his death as a piece of the ship is blown up by Utsuro's cannons. All while Nobume watches him fall with a smile on his face.
67** In recognition of his efforts both the Shinsengumi and Mimawarigumi salute together while facing the sun. Nobume writes one last message to him on a phone, thanking him for her name, before she throws it overboard.
68** To end the arc, the Shinsengumi are forced to leave Edo for their own safety. Before that, they each bid farewell to different people. Kondo goes to the Shimura house, where both Otae and Shinpachi appear to accept him and welcome him to visit next time. Okita fights one last time with Kagura to see who is strongest. Finally, Hijikata eats together with Gintoki at their favorite place, both laughing as friends. After this, the Shinsengumi take their leave for who knows how long.
69* Battle on Rakuyou arc:
70** In Chapter 555, Kagura decides to temporary leave the Yorozuya in order to find her family (Kamui and Umibozu). The sad part comes since Kagura was really sad about that decision. On a heartwarming note, [[TrueCompanions Gintoki and Shinpachi also leave and follow her]].
71** In Chapter 559, Kagura visits her mother's grave and remembers her past. She promised to return with her dad and her brother... but despite them now being on the planet, they aren't reunited.
72** Katsura's past: Having lost his parents at an early age, Katsura and his grandmother became homeless and had to live on the streets. She eventually died and left him behind as well, reminding him to survive at all costs, no matter how cowardly he has to live and no matter how lonely it gets. The nickname "Zura" was revealed to be Gintoki's attempt of making Katsura feel at ease around his friends.
73** Sakamoto's reason that why he is not using a sword: he simply can't since he got a heavy injury, courtesy of Batou, making it impossible for him to use a sword again. Takasugi and Gintoki offer some words of comfort and inspiration to him before leaving to find Batou, visibly pissed off and seeking revenge. Gintoki's murderous intent was so great Batou sensed it from a distance while fighting someone else (Pakuyasa to be exact). In the present, the aloof Gintoki becomes a lot angrier once Batou ridicules Sakamoto and he goes out of his way to stab his sword-wielding hand, which implies he's still saddened by the tragedy.
74** TheReveal in the backstory of how Umibouzu met his wife Kouka and then what led to her death that made Kamui the way he is today. She was an immortal like Utsuro who feeds off the Altana of her planet and being away from it led to her illness and eventual death. It is unknown how many centuries she had been living alone with neither food or human interactions before meeting Umibozu.
75** The expansion on Kagura and Kamui's past: as it turns out, Kamui used to be a gentle child who did everything to protect his mother and little sister in place of their father. He takes on everything alone and constantly tries to get stronger to keep them safe, but no matter how much he tries nothing gets better: their family is always targeted by local hoodlums, mother is dying and father is never home. As Kamui was on the verge of collapsing, he overheard the story of how his parents met and found out Umibouzu was the one who took Kouka away from that planet, making him the one responsible for her state. The stress from dealing with everything alone, the pain from seeing his mother's declining health, the emptiness from his father's absence, and the newfound anger for his father eventually broke Kamui, causing him to give in to his violent Yato nature and try to kill Umibouzu, breaking their family apart. His desire for power was twisted into a dark obsession, making him the cheerful psychopathic bloodknight he is today.
76** The fight between Kamui and Kagura ended with Kamui - unable to attack his little sister - collapsing. As Kagura held him close, Kamui saw the image of his mother in Kagura and started to let out the tears that he had been holding in since childhood.
77** The whole history of Utsuro, starting from how he came to be to how his personality Shouyo was killed by his nature Utsuro at the same time Gintoki executed him.
78** Oboro's backstory and dying words to Takasugi about how Utsuro came to be and him being responsible for his capture, which he came to regret as he wished to make friends with the other disciples Shouyo made. ''Takasugi'' decides to pay his respect by taking Oboro back to Earth for a proper burial, along with resolve to stop Utsuro once and for all.
79** The arc ends with Kagura saying farewell to her mother along with her home planet as they go back to Earth... for the final battle.
80* Silver Soul Arc:
81** Chapter 609, with one of the downright cruelest examples of Mood Whiplash ever put on paper. Gengai reveals that the Neo Armstrong Cyclone Jet Armstrong Cannon, a downright ancient gag from the series, has been built and is ready to fire on the enemy fleet. A quick dirty joke is made (Kintoki and Tama are needed to fire the cannon, Kin + Tama = slang for testicles), and as the chapter ends we are suddenly informed that this is a suicide attack and that both Tama and Kintoki are about to die.
82** Chapter 610 makes the previous chapter look like an absolutely joyful affair. Barely functioning after the blast, the nanomachines tearing her to pieces from within, Tama stumbles out of the pod and collapses. The Yorozuya rush towards her screaming her name in fear of the worst while her life flashes before her eyes, and she dies in Gengai's arms. Jesus Christ, Sorachi. Gengai's reaction is what takes it from heartbreaking to outright soul-crushing, especially considering Gengai has just lost his children for ''the '''second''' time''.
83--->'''Gengai:''' "Why are you all so quiet? Why don't ya spit out some bitter words of hatred? I know these pieces of junk can't talk too well, even at the best of times... but why ''now'', of all times... do they have to put on those admirable faces... and silently break down... Machines are meant to be of use to people. That's certainly true. But if you had said that you didn't want to, I don't think I would have minded. Even if you don't serve a purpose... even if you are pieces of junk... If I am with you, my friends... ''I'm ready to drop dead beside you.'' Yet I... I'm sorry. I'm so sorry.
84** During chapters 640-642, Henpeita and Bansai each decide to go through a HeroicSacrifice to stop the Hinokagutsuchi and/or buy time for Takasugi. While Henpeita is shown to have survived later on, Bansai's death is confirmed.
85** Chapter 649: Nobunobu dies. Indeed, he was recognized as the shogun even for that short time leading the country, but he dies knowing that.
86** Sadaharu's sacrifice to keep back the overflowing Altana from destroying the Earth. It's revealed that it shrunk to a very small size and it's stuck inside a ball.
87** Chapter 669 begins the two-year timeskip, and it establishes that Shinpachi is now carrying the Yorozuya name on his own. It's shown in a flashback that this arrangement was mutual, as Kagura and Gintoki had other motives to focus on, but seeing the trio say their goodbyes and go their separate ways is bittersweet at best.
88** Kagura tells Shinpachi that even though two years passed, she still hasn't found a way to turn Sadaharu back to normal.
89** The anime adaptation's ending outro, which goes through every single episode in the anime and so includes many posthumous characters from previous episodes/chapters.
90** Chapter 703: Shoyo admits that if he hadn't met Gintoki, Katsura and Takasugi, they wouldn't have met the harsh fate of having to fight Utsuro. He also says that he is not worthy of being called their master and that he wasn't able to save them and they saved him instead.
91*** Takasugi dying in Gintoki's arms. Takasugi tells him that although the last thing his left eye saw was Gintoki's saddened face, he doesn't want the last thing his right eye sees to be Gintoki's disheartened face.

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