While it can sometimes be cathartic to watch a particularly nasty villain die, the same can’t be said when the villain is sympathetic. The saddest anime villain deaths tend to involve evildoers whose motivations make sense, as most people can relate to the bad thoughts that enter one’s mind when pushed into a corner. If a villain was clearly birthed from extreme pain, it’s hard not to feel a little sorry for them, even if they also eat babies sometimes.
9. Vegeta — Dragon Ball Z
While some of the pathos is sapped from Vegeta’s death by the fact that he comes back to life later in the series, it’s still one of the most painful moments from Dragon Ball Z. During a battle with Frieza, Vegeta is fatally wounded. As he dies, he explains to Goku that Frieza is responsible for the destruction of their planet, and begs Goku to defeat him.
Goku refuses to acknowledge the truth that Vegeta used his last breath to convey, and tells him to stop talking and save his strength. While Goku may have meant well, it still comes off as a little dismissive.
8. Tsubaki Kasugano — Future Diary
Future Diary has plenty of tragic villain deaths, but Tsubaki Kasugano’s is one of the most painful. As a child, Tsubaki was forced to act as the false prophet for the Omekata cult. She’s coerced into feigning clairvoyance, and her blindness makes it impossible for her to leave the temple.
Just as Tsubaki’s parents are about to relieve her of her onerous duties, another cult member named Funatsu kills them, and restructures the cult with new rituals. One of those rituals involves encouraging members to rape Tsubaki, as that will allegedly cleanse them of sin, and she essentially spends the next two years as a sex slave.
After she finally escapes, Tsubaki wants revenge on the entire seeing world, as she holds everyone responsible for her suffering. Using her powerful Clairvoyance Diary, she attempts to murder Yuno and Yuki, and orders her followers to sexually assault Yuno. When Yuki finally kills her by destroying her diary, he does so by distracting her with the handball that her mother gave her as a child, as it’s the only thing that kept her sane as she was enduring years of torture. It represents her only memories of comfort and love, but it appears too late. As she dies, she bursts into tears, and so do some audience members.
7. Legato Bluesummers — Trigun
What’s sad about Legato Bluesummers’s death has nothing to do with the villain’s personality. While there’s something to be said for his tragic backstory, he’s also kind of a nihilistic jerk whose sole mission is to ruin the life of Trigun’s protagonist, Vash.
What’s truly painful about Legato’s death is that Vash is forced to kill him, even though he swore an oath that he would never take another life. Watching Vash grapple with the implications of breaking his promise is truly devastating.
6. Angelina Dalles — Black Butler
Black Butler features a number of tragic deaths, but Angelina Dalles’s is one of the most painful. Angelina is one half of the serial killer team Jack the Ripper, but she wasn’t always inclined to such brutality. At one point, she was a kind, caring person who loved her family, and she even became a doctor in hopes of curing her sister’s severe asthma. However, after her entire family is killed and she loses the ability to bear children, she freaks out and starts murdering patients who request abortions.
Angelina teams up with the Grim Reaper Grell Sutcliff, and the two of them kill with abandon. Eventually, Grell tries to push things further than Angelina is willing to go, and when she refuses to kill her nephew who she loves like a son, Grell ends her life. Despite the severity of her crimes, it’s hard not to feel for her when she dies for showing a loved one mercy.
5. Caster — Fate/Stay Night
Caster of Fate/Stay Night spent most of her life being treated like a criminal. She’s been mind controlled and forced to hurt others against her will, castigated as a witch, and abandoned by the only person she truly trusted. Eventually, she decides to start actually doing all the evil things everyone blames her for anyway, and she even goes so far as to drain an entire town of its energy, nearly killing all its inhabitants in the process.
Despite all this, she does form a meaningful bond with Souichirou Kuzuki, a serial killer whose interests she serves. As the two are dying together after Archer defeats them, they finally confess their love for each other. Though Caster claims to be happy with the short time they spent together, the admission comes far too late, as she never had the chance to experience real happiness.
4. Matthew — The Ancient Magus’ Bride
In the early episodes of The Ancient Magus’ Bride, a man named Matthew temporarily fulfills the role of villain, and his story is utterly heartbreaking. Matthew wanted desperately to improve his sickly wife Mina’s health, and when nothing else worked, he asked a sorcerer for assistance. The sorcerer instructed him to use cats — who have nine lives and can be repeatedly killed — to create a life-giving potion. Desperate to save his wife, Matthew followed the sorcerer’s instructions, but the potion ended up killing Mina instead of helping her. The sorcerer apparently expected this outcome, and Matthew completely loses his sh*t and starts murdering every cat he comes across.
Eventually, the cats fight back and kill Matthew, but his spirit ends up entangled with Mina’s in the middle of a lake, and it’s up to protagonist Chise Hatori to help the couple move on to the afterlife. When the two finally pass over to the other side, it’s heartbreaking because Matthew was once a decent man who became desperate enough to be manipulated into villainy.
3. Kagura — Inuyasha
Kagura is a wind sorceress who was formed from the flesh of Inuyasha’s top villain, Naraku. Though she’s forced to obey her originator, she hates him, and takes every opportunity she can to undermine his authority. When she finally openly defies him, he retaliates by dealing her a fatal wound.
As she’s dying, Sesshomaru, Inuyasha, and the rest of the crew arrive, but they’re unable to do anything to save her. Her body evaporates and becomes one with the wind, but she’s happy to die because she’s finally free of Naraku.
2. Meruem — Hunter X Hunter
Meruem of Hunter x Hunter is a half-human, half-insect hybrid who sees humans as inferior scum who are livestock at best. He’s so callously violent towards them that he has no gripes eating a human baby. All that changes when he meets Komugi, a blind girl who plays a game called Gungi with incredible skill. The two forge an unexpected friendship that helps Meruem learn to respect and care about humans.
Before Meruem can change his behavior patterns, he’s poisoned during a battle with Nereto. Knowing that he has no chance of survival, he drags himself to Komugi for one last game of Gungi. However, he doesn’t want to infect Komugi with the contagious poison, and soon attempts to leave. Before he can make his exit, Komugi stops him, as she refuses to let him die alone. After several more games of Gungi, Meruem dies, and Komugi follows soon afterward.
1. Momochi Zabuza — Naruto
Naruto practically invented the concept of tragic villain deaths. Just about every antagonist is sympathetic in some way, and almost none of them survive. However, the first character to fall victim to this trope is Momochi Zabuza.
When he’s first introduced, Zabuza is working as a bodyguard for a corrupt businessman named Gato. What Zabuza really wants is to kill the Mizukage (the leader of his nation), but he needs money to continue his quest after the first coup d’état failed. Zabuza is aggressive, arrogant, and willing to kill anyone who stands in his way, but there’s another side to him that’s a little less in your face. Although he claims to see the orphan Haku as a tool, it’s clear that he cares deeply for the boy. When Haku dies trying to save Zabuza’s life, the villain is devastated, though it takes time (and a lecture from Naruto) for him to admit his true feelings.
When Gato shows up and attempts to defile Haku’s body, Zabuza kills him, but dies in process. He never got the chance to act on his paternal love for Haku, or to thank him for saving his life.