Top 20 Saddest Anime Moments Of The Century (So Far)

Welcome to WatchMojo, and today we’re counting down our picks for the Top 20 Saddest Anime Moments of the Century So Far.

For this list, we’re letting loose the waterworks as we look back on the scenes in anime that broke our hearts due to their upsetting content. Prepare yourselves for spoilers and self-loathing. Think we missed an absolute tear-jerker? Let us know in the comments!

“Attack on Titan” (2013-)

The Final Season gave us no shortage of revelations, but none were more painful than watching our favourite meat eater slip away. While making their escape from Marley aboard a blimp, the Survey Corp come under attack from a surprise passenger as Gaby sneaks aboard, locked and loaded. It just so happens the one shot she fires finds its mark, right through Sasha. It’s a brutal end to one of the purest members of the original cast, perfectly setting the stage for the savagery to come.

“Bungo Stray Dogs” (2016-19)

Before Dazai was the ultimate bro seeking atonement, he was a ruthless enforcer of the Port Mafia, willing to commit whatever atrocity was needed if it meant accomplishing his mission. So, what changed him? His best friend perishing in front of his eyes, that’s what. Seeking revenge for the murder of his adopted children, Oda waged a one man against those responsible, the encounter proving to be fatal for everyone involved. Even with his death wish, Oda still used his dying words to impart wisdom to Dazai; that at the end of the day, it’s better to live as a good person.

“Monogatari Series: Second Season” (2013)

By now, we’ve gotten pretty used to Araragi trampling on the hearts of the many ladies in his life, though this little farewell still cuts the deepest. Originally a mischievous spirit incapable of moving on, Hachikuji became a somewhat vital member of the Araragi’s ever expanding harem. At least until her business on the mortal plain was finished and was slowly being taken to the big upstairs, something the pseudo-vampire is none too pleased about. Knowing that this may be the last time they see each other, Hachikuji makes one last bid for best girl status before disappearing into the unknown.

“To Your Eternity” (2021)

He suffered through the world alone for his early life, only to find family, grow up to become the ultimate chad, and was willing to die for love. Our dragon boy was one in a million. Following his death after protecting Rean from being buried by rubble, Fushi decides to lie to her, assuming Gugu’s form to give her a false sense of happiness. It may have been a kind gesture, but Rean isn’t so easily fooled. We later see her resting by the place where Gugu first saved her life, proclaiming that she will always love him, never be married to anyone else, and is aware he is no longer alive. Why does this anime keep torturing us?!

“Haikyu!!” (2014-20)

Nobody likes losing, but alas that’s the way of the game. Sadly, for Karasuno, their bout against Aoba Johsai resulted in them falling flat on their faces, and while they would eventually go on to soar again in the rematch, they first had to feel the sting of defeat. The saddest part isn’t watching the game reach its conclusion, it’s the aftermath where the coach treats everyone to a meal. Silently, all the members of the volleyball team eat, as well as weep over their loss. It’s such a painfully human reaction you can’t help but be moved by it!

“Demon Slayer: Kimetsu no Yaiba the Movie: Mugen Train” (2020)

He set his heart ablaze, he fulfilled his duty, and the only thing that it cost him was his life. While his strength as the Flame Hashira is undeniable, Rengoku was put through his paces against the demon Akaza. Left horrifically wounded from the encounter, all the eternally optimistic swordsman can do is pass down his final will to Tanjiro, while also giving his blessing for Nezuko to join their ranks despite her affliction. It’s a beautiful send off to such an inspired character, with the visions of his mother only adding to the heartbreak.

“86” (2021)

The robotic dog of Spearhead Squadron has been around since the beginning, though it mostly lingered in the background. As it turns out, that also allowed it to capture the small yet meaningful moments of its new family throughout its tenure. As the remaining 86s venture out beyond their confinement, we’re greeted to a montage of all the fun moments Shin and the rest have had as team-mates. They may seem insignificant, but when weighed against the cruelty they have endured, it comes across as rather heart-warming. Then we discover that Fido is playing these during its last moments, on account of it and everyone else being overrun by the Legion. Good dog.

“My Hero Academia” (2016-)

All Might’s one and only sidekick, Sir Nighteye is a hard man to please and even harder to measure up to. Capable of seeing into the future, his cold persona spawned following a wedge that was driven between himself and the World’s Greatest Hero, due to the latter’s reckless disregard for his own life. And yet his death still hit us like a truck, mainly due to him finally letting down his walls and showing his appreciation for his mentor as well as his student. Giving Mirio hope that he can continue on as a hero even without his Quirk was absolutely precious.

“March Comes In Like a Lion” (2016-18)

Bullying is always a subject that strikes deep, and when you combine it with someone as good-willed and lovable as Hina, you’re just asking to choke up. While usually resilient, Hina can’t help but confess to Rei that she’s terrified about going to school on account of her knowing she’s going to be the target of bullies, all because she defended her friend. Even so, she still refuses to change her way of thinking. It’s such a profound moment of introspection that it not only moves Rei, but also has us blubbering. She’s too pure a soul to have something like this happen!

“Violet Evergarden” (2018)

Violet’s job as an Auto Memory Doll enabled her to encounter all manner of individuals, each with their own personal pains and stories to be typed out, though none packed quite as much of a punch as this. As a dying woman has Violet write out an increasingly large amount of letters, we see events unfold through the eyes of her daughter Ann, who grows increasingly frustrated over the whole affair. Then we find out that each letter was addressed to Ann, one to be delivered to her on her birthday for the next fifty years. It’s an unfathomable example of love between mother and daughter, and we were not prepared for it.

“One Piece” (1999-)

Even amongst oceans filled with war and death, the end of Fire Fist Ace remains the events that still roceds us to our core. In spite of doing everything possible to free his brother from the executioner's block, Luffy can only watch in horror as Ace leaps in at the last second to save him from Akainu, and as a result is impaled by a burning fist. With no chance of escaping death, all Ace can do is give his final words of thanks to his younger sibling, before perishing on the battlefield, content that he had people who loved him regardless of his heritage.

“Kaguya-sama: Love is War” (2019-20)

The most aloof member of the school council, the anime kept us guessing as to what his deal was. Did he have any skeletons in his closet or was he just a naturally depressed teen? Turns out that he had every right to be cynical on account of having a nightmare past. After beating up a popular jerk who was threatening to use his own girlfriend for revenge porn, the whole school turns against Ishigami due to malicious rumours, where he is shunned and looked down upon. It’s a bleak example of how gossip can destroy a person’s life. Thank goodness he had someone like Shirogane to bring him out of that dark place!

“Naruto Shippuden” (2007-17)

He may have been a perverted hermit, but when it came down to it, Jiraiya was the aged underdog we couldn’t help but love, especially given the parental bond he shared with Naruto. While his Sage Mode and veteran shinobi experience made him the ideal match to take on the Akatsuki leader, he woefully underestimated what Pain and the Rinnegan were capable of. While it resulted in his death, instead of letting despair overtake him, the old frog pulled out one final trump card; sowing the seeds for Pain’s defeat and entrusting his will to Naruto.

“Fullmetal Alchemist” (2003-04)

No matter how much Brotherhood excels in other areas, nothing can measure up to how broken this scene in the original outing left us. Following on from his murder at the hands of the Homonculi, Hughes is given a soldier’s burial with the highest honours. Not that it stops his confused daughter from wailing out as he’s lowered into the ground. Between seeing Hughes’ family break down and Mustang silently crying for his dear friend, everything seems hopeless, especially knowing those responsible for the killing stand among the grieving.

“Sword Art Online II” (2014)

Alas, there’s no such thing as a respawn when you receive a game over in the MMORPG that is life! Standing in as Asuna’s newfound gaming companion throughout her solo adventure, it turns out that Yuuki’s real-life predicament was much more dire than any boss fight. With limited time left due to a terminal disease, all of her online friends decide to give her the best send-off possible. Moments away from death, Yuuki is logged back into the gaming sphere, where she can be with Asuna and the gang right up until she passes over.

“Gurren Lagann” (2007)

His existence may have been brief, but he outshone everyone else all the same. Originally nothing more than a shirtless wonder with no shortage of bravado, Kamina eventually grew to become a beacon for humanity in the wake of the Beastman incursion, kickstarting the rebellion with nothing more than a smile. While his demise ultimately allowed Simon to flourish as a main character, we still can’t help but wonder what might have been if episode eight never came to pass. Probably something involving Yoko and drilling. We still miss you, big man!

“Code Geass” (2006-08)

As both a masked liberator and a tyrant, Lelouch broke every shade of grey out there, to the point where you never knew how he planned to secure his dream of destroying Britannia, and at what cost? Turns out, once again, he had the whole world fooled. Setting himself up as the ultimate despot, Lelouch made himself the symbol of villainy, something all peoples could rally around in their unified disgust, only to then grant their wishes by arranging his own assassination. It’s an unimaginable act of self-sacrifice, proving that underneath all the moral ambiguity, Lelouch was so much more than a monster.

“Clannad: After Story” (2008-09)

Losing a wife at such a tender age was already brutal enough, surely the anime wouldn’t be so vicious as to rob Tomoya of his child too, right. Right? Wrong. Contracting the same diseases as her mother, the adorable Ushio finds herself at death’s door at only a few years old. All her father can do is clutch her as she fades away amidst the snowfall, handing us a double whammy of misery. No amount of magic lights and inexplicable resurrections can make us forget the pain of watching this!

“Angel Beats!” (2010)

You’d think leaving Limbo would be cause for celebration, but not here. As Yui’s past life is revealed as a paralysed girl who never got to experience the joys of life, Otanashi endeavours to help her live out all the things she missed out on. At least until it comes to marriage. That’s when Hinata steps up to the plate, not only agreeing to marry her but promising to find each other should they ever be reborn. It’s a beautiful moment, one that bites deep when Yui’s wishes are fulfilled and she finally passes on. The added montage that displays what could have been between the two will break your spirit.

“Made in Abyss” (2017)

It may have been a mercy but that doesn’t make it any less traumatising. Reduced to a sentient, immortal blob due to being exposed to the Curse of the Abyss, Mitty faced a hopeless future filled with agony and loneliness, unless Nanachi finds a way to end her life. As it happened, Reg’s Incinerator proved to be the only thing capable of dealing death to the undying. Even though she’s finally able to bring her friend peace, Nanachi can’t help but break down over losing her beloved companion. Damn you Bondrewd!