So, there's a villain. Right. Murdering, world-conquering type. The series is ending, so it's time to get rid of him. Slowly and painfully. So he goes out with... a final touching quote and a One-Woman Wail?
As odd as it may seem, if you want the audience to feel sorry for a villain, a good death scene is probably the way to go. This works best if you know their Freudian Excuse; Chaotic Stupid need not apply for this sort of thing. Also works easier if this is a supporting villain. This is easiest to do with a Big Bad's minions: we can identify with The Dragon, and especially the Quirky Miniboss Squad, over time and may be sad to see them go. If a Fallen Hero dies, expect everyone to weep openly. A few well-chosen Last Words may also be used to create this feeling.
Note that if you want the audience to take the scene seriously then you have to add some humanizing elements to your villain beforehand. See Likable Villain for ways in which this can be done. Neglecting to do this may result in Narm or just confuse the audience.
A Woobie, Destroyer of Worlds and other kinds of Tragic Villain are the best choices, but any case of a genuinely well-done Anti-Villain will do. Also note that this is primarily about the story showing how sad a villain's life was, not how some of the audience will interpret it.
Compare Draco in Leather Pants, Cry for the Devil, What a Senseless Waste of Human Life, Antagonist in Mourning, and Death Equals Redemption. See Monster Sob Story when the villain's death isn't required to garner sympathy. Do not confuse with Alas, Poor Scrappy (though it can overlap). Or Alas, Poor Yorick for that matter.
As a Death Trope, several if not all Spoilers will be unmarked ahead. Beware.
- Lord Zarak (A.K.A. Scorponok)'s death in The Transformers. This could seem to not count, since he was trying to stop Unicron, and therefore not dying in a villainous way, but remember that he was the Decepticon leader at that point.
- Moloch in Watchmen. It was made more poignant because, on many levels, it had more to do with Rorschach than him. This part:
Edgar Jacobi: Heh. Well, you know that kind of cancer that you get better from eventually?
Edgar Jacobi: Well, that ain't the kind of cancer I got.
- The League of Extraordinary Gentlemen
- Mr. Hyde singing "You Should See Me Dance the Polka" as he jaunts off toward the tripod is particularly emotional when it hits you that, for all his unbridled depravity, you'll never experience his brilliantly dark humor again. Throw in his unrequited love for Mina, and it gets exponentially more difficult to read.
- It's also a bit difficult not to feel bad for Moriarty, given the horrifying manner of his death.
- Asajj Ventress from Star Wars: The Clone Wars. She is given sympathetic qualities in the middle of the series, and her journey to sympathetic-ness is completed at the very end when her hero and mentor, Count Dooku, orders her shot to death because he can't be bothered to wait for her. She makes one last pitiful attempt to kill her nemesis, Obi-Wan Kenobi, and is cut down by Anakin. As she lies dying, she reaches out for Obi-Wan and tells him to watch the Galactic Core and Coruscant. Her final words finally reach this territory:
Obi-Wan: I thought you'd use your dying breath to curse us.
Asajj: Perhaps I have...or perhaps I just...hate Dooku more than I hate you....Or maybe...you were right about me...all along....
- When Destro was thought to have died in Marvel's G.I. Joe series, Snake-Eyes and Scarlett laid flowers at the place where he supposedly died.
Lady Jaye: You fight somebody long enough, you get to know them... and after a while — you start to respect them.
- The Transformers: Last Stand of the Wreckers: The Decepticon Snare, The Predators security director, is stuck at G-9 under one of the most sadistic Decepticons ever, Overlord. Despite him, and many other troops, disturbed and uncomfortable with everything note , Snare throws a Spanner in the Works by freeing Impactor, and later leading some of the Autobot rescue team to save the rest of them. In the scuffle, he's shot and lies dying, asking Impactor to kill him before Overlord comes and finds what he's done. Impactor does so after thanking him.
- Batwoman: Abbot, the werewolf leader of the Religion of Crime Cult. Throughout the series he saves Batwoman at least twice (though is at odds with her because he's a criminal who withheld information about her sister and was part of the cult that tried to kill her) and leads his troops into battle against Medusa's forces. Despite being afraid of Medusa and her power, he still chooses to stand with Batwoman, and tries attacking Medusa from behind. Medusa catches him, petrifies him, and shatters his body. Batwoman looks at his remains sadly, and later uses a piece of mirror to give Medusa the same fate.
- Daken: The title character has done this twice. The first time, he broke down while dying, asking to see his father and apologising for placing a bomb at the Jean Grey Academy, before immolating himself with a bomb. The second, in which he inexplicably came back from the dead, involved him imagining how life could have been with his father and mother, had she not been murdered by Romulus. Wolverine is then forced to drown him to kill him, as by this point he is little more than a pawn for Sabretooth to use against him. Wolverine himself then breaks down, realising they could have had a happy life too. Considering Daken was The Sociopath most of the time... damn.
- After gleefully spending The Killing Joke crippling Barbara Gordon and torturing her father James, The Joker starts off the story absolutely evil, but his last few monologues leading up to his defeat transform him into a sympathetic lunatic who truly does believe life is cruel and pointless, and that all of Batman's attempts to redeem him are hopeless. Instead of his typical Batman beatdown, he tearfully shares a joke with the Dark Knight, and the two of them actually laugh together in the rain while the cops arrive.
- John Genovese, sort of. Big Daddy drove him nearly to madness, and all because Big Daddy wanted to live his childhood fantasy and chose him as the villain.
- Chris Genovese, who dies saving Mindy and asking her to apologize to his mother for ruining her life.
- Thanos in the 70s crossover between The Avengers and Adam Warlock. He's an Omnicidal Maniac who wanted to destroy the entire galaxy to impress Mistress Death, but is turned to stone by Warlock. The last panel shows a tear rolling down his now-petrified face, mourning for his lost love.
- Discussed and subverted in Terra Obscura. The Grim Reaper was once a great hero, but turned bad and ultimately died while attempting to assassinate some old friends for the mob. At the end of the first miniseries, he's buried with the other casualties of the story in a hero's graveyard, complete with a marble statue of himself for a tombstone. However, none of the heroes attending the funerals believe he deserves it — it's just a political move to keep his actions from ruining their reputations.
- In the Sin City album Hell and Back, Wallace feels some pity after he kills Deliah, the contract killer who tried to seduce and kill him, calling her a "strange, sad creature" before silently closing her eyes.
- The Crime Master in the end of Agent Venom's first volume. Not only does he get shot dead by his own sister but his last words, rather than swearing vengeance or cursing his enemies, are just this:
- Toxin gets a similar reaction from Venom mainly because he was forced into the role and died before Venom could save him.
- When the first Porcupine (Alex Gentry) died helping take down the Serpent Society, Captain America was deeply saddened by his old foe's demise and even insisted on giving him a memorial in the Avengers Mansion, a right usually reserved for longtime Avengers and worldchanging heroes. Given that Porcupine was a Friendly Enemy to Cap at best and an Ineffectual Sympathetic Villain at worst this isn't terribly surprising.
- The Pride's demise at the end of the first arc of Runaways. All the evil and bloodshed they did was to build a better world for their children (the heroes), and they're all unceremoniously slaughtered by the Gibborim after their plan fails. Special mention, though, goes to the Minorus, whose last act is to take a final stand against the Gibborim to save the Runaways, and the Yorkes, who sadly watch their daughter escape and reflect on their own descent into villainy.
"So this is what we're reduced to, eh, mother?""Yes, love. Empty nesters."
- Claudine Renko, AKA Miss Sinister. Despite what she tries to do to X-23, it's still pretty easy to sympathize with Claudine: She's a victim of Sinister's experiments, and never volunteered to be the vessel by which he attempted to cheat death. On top of that, now he's Fighting from the Inside to steal her body as a Clone by Conversion, which will effectively kill Claudine in the process as he overwrites her mind and fully transforms her body into his. The poor woman just wants to survive with her mind her own.
- Robin Series: Young El gets this treatment when he gets pinned by a support beam in a building that is quickly flooding while Robin tries to save him. Tim can't lift the beam and El drowns to death when Tim's rebreather runs out, he's still a gang banger with at least one murder and six attempted murders to his name but Tim is crushed that he drowned while Tim was right there and helpless to save him, and his scared reaction when he realizes he's probably going to die reminds the reader he's just a teen the same age as Tim.
- Dick Tracy: The final arc featuring Big Boy Caprice had several of these. There's the explosion that claims the life of bomb-maker Little as his wife looks on in horror, the pathetic exit of a broke convict hoping to get rich by killing Tracy, and the death of the hired killer known as the Iceman, who was just starting to feel something for Sparkle Plenty. Perhaps the most depressing of all may be the death of Big Boy himself, who dies alone, abandoned by his henchmen, and cut off from all the power that once made him feared. Tracy may think Big Boy was a Karma Houdini, but the audience isn't likely to agree.
- Max Griffin in Amulet. After the death of his friend, Layra, he proceeds to spend the next fifty years on a superpowered revenge-fuelled rampage, kept alive only thanks to a deal with the Amulet Spirit. Still, its hard not to feel a little bit sorry for him when he lets the Spirit withdraw their power, making Max rapidly age to death after a memory of Layra calls him out for all the terrible, terrible things he did in her name.
"I did it - I did it for you.""No, Max. You did it for you."
- Though rare, it is not unheard of for this to happen with Voldemort in Harry Potter fanfic. One such fanfic used a spell to make Voldemort revert back to the boy he was before he became evil (handwaving the fact that in canon, young Mr. Riddle was screwed from the beginning), and then Harry held him and comforted him while the shock of all the terrible things he had done slowly killed him.
- Of all the villain deaths in The Immortal Game, the only one that earns any audience sympathy is Empyrean. He's only a villain because Titan forces him to, and isn't even all that good at it. His mini-Villainous Breakdown when the Mane Six break into his throne room and strip him of his power is pathetic, and it's hard not to feel sorry for him when Titan shows up, decides he's useless without his powers, and kills him while he begs his father for mercy.
- The Pony POV Series has a couple of examples:
- Destruction. Despite being literally addicted to destruction, he was also the most sympathetic of all the draconequi, as he hated his addiction and wished he didn't have it at all. His desire in the war with the alicorns was to cause so much destruction he'd finally be rid of it once and for all. Him being killed and eaten by his own brother is extremely tragic.
- Also kind of hard not to feel sorry for the Master in the Dark World, who the Valeyard subjected to the same thing Discord did to the Doctor (namely, being killed repeatedly with him regenerating each time). What's worse, according to Word of God, the Valeyard's claim to keep killing him until he gets a good personality was just an excuse to kill him over and over again.
- Despite spending a thousand years massacring entire families with no remorse, following Discord's orders without protest, and generally being the biggest Jerkass in the Dark World, it's pretty hard not to pity Angry Pie when Twilight gives her a HUGE No-Holds-Barred Beatdown in "Cold Hoof Blues". By the end of the chapter, Angry Pie is crying and begging her foals to forgive her for failing to succeed in her task to bring them back to life. Even the other heroes (whom Angry Pie just tried to kill) are shocked and horrified by Twilight's actions. Thankfully, they manage to talk Twilight down and she ultimately redeems Angry Pie with a reverse Memory Spell (showing her Twilight's memories instead of her own).
- Similarly, it's hard not to feel bad for Dark World Fluttercruel, even after all she's done, when she watches Discord get literally stabbed in the back by Rancor, which she simply cannot comprehend. She ends up crying and pleading with Discord to absorb her to heal himself. It shows that despite all else, she's still a foal who deeply loves her father and doesn't want him to die. What's she like by the end of the final fight with her? A broken little child who by that point knows her actions were wrong but is too driven by her Undying Loyalty to her father to make a HeelFace Turn.
- Although the main timeline Master is a total asshole who has committed unbelievable atrocities, his final fate is pitiable. His essence is trapped in a fob watch that Minuette feeds to the Blank Wolf, and he spends his final moments begging for his life. In his desperation, he even swears on Entropy's name that if he is spared, he will never hurt anyone again (a promise that cannot be broken, as Entropy will erase anyone who takes her name in vain). Unfortunately for him, Minuette has no idea who Entropy is and does not understand the significance of the promise, so she kills him anyway. The Doctor senses his demise and mourns him.
- The Blank Wolf eventually gains emotions and is able to think for himself. He understands that if he kills Shining Armor, he will ruin the timeline, but no matter how hard he tries, he is unable to fight his programming that orders him to destroy Shining Armor. Shining Armor understands, and sadly gives the Wolf a salute when he finally manages to slay him. The Wolf is eventually reborn as a puppy during the Finale Arc.
- In the Pony POV Series Chaos Verse (a spin-off of the above), the death of Big Bad Nightmare Phobia invokes this. In her final moments, she recovers her lost memories and realizes just how in the wrong she was. Her last act is to reach out to Celestia and Discord longingly before dying. Luna even mourns for her afterwards.
- Talen is this for Ursula, and easily becomes Head Canon for those wondering how she grew up to become the movie's manipulative, power-hungry witch. (Hint: it involves a Freudian Excuse of Fantastic Racism and an all-too-realistic case of Ain't Too Proud to Beg.)
- A Growing Affection has a couple of cases.
- Karin gets just enough time to ask Sasuke for a fake show of affection. Sasuke gives her a real kiss, and she dies in the middle of claiming that he really did love her.
- After Gouki commits Suicide by Cop, his last words are to hope that his wife will be able to find happiness in the new world. Word of God says he died without knowing she was pregnant.
- The immortal lion cub Shocker in The Lion King Adventures is a good example of this. Despite being a truly despicable character, his fate is rather harsh. He is buried alive, and, being immortal, is forced to choke on dirt for all eternity.
- Mega Man: Defender of the Human Race has Ballade, who makes a not-quite heroic sacrifice in order to save a little girl trapped where he was ordered to detonate explosives.
- Hivefled: Dualscar was a slave-taking Jerk Ass who tried to have his ex murdered, but it's hard to imagine he did anything that would make him deserve the death he got.
- Young Justice: Darkness Falls: Volcanna in this fic was a lustful fire wielding fury who caused nothing but trouble for the league and team, and had a rather unsettling obsession with Superboy. However, her dying for her comrade Big Barda when they decide to desert the furies was a surprisingly touching moment, and her death was treated not with contempt but with sympathy.
- In the My Little Pony/Dresden Files crossover The Dresden Fillies False Masks, the entire Order Triune becomes this. They are sacrificed to a demon by Novel Notion. Considering they spent the whole story trying to kill Harry thinking he was someone who had been dead for 1200 years, endangered many lives, and betrayed the very kingdom they swore to protect, it is karmic. But it becomes tragic when you realize that they had been misled this entire time, they genuinely wanted to protect Equestria, and had been betrayed by one of their own. The way they go is also terrifying: running for their lives as the circle swallows them, with the pegasi who tried to fly away being swat down like flies. Afterwards, all that's left of them is some blood. The horrified reactions of the Mane 6, and even Harry, seal this.
- In the supercrossover military fanfiction series, The Terminators: Army of Legend, the antagonist of Volume V, Zack Dawson, can be considered this. Even doubly painful considering his relationship with series protagonist Alex Vaughn.
- In Dreams About Friendship are Magic, fake Celestia was disturbingly clingy to Twilight, and tried to keep her in what was pretty much a coma for the rest of her life, but because she goes out sobbing pitifully, begging Twilight to be with her and telling her how much she loves her, it's easy to feel sorry for her.
- In Kill Or Be Killed, Taeyeon's death. She was only turned to darkness because she wanted to avenge Leeteuk's death, but it grew to the point where she had to be killed by one of her own group members to stop her. Right before she dies, the POV switches to her as she reunites with Leeteuk in the afterlife.
- In The Little Pony Legend, despite all the horrible things done by them, Korra genuinely mourns the deaths of Tarrlok and his brother, saying that losing her bending was now the 2nd worst thing she experienced today.
- In My Mirror, Sword and Shield, Suzaku and his family had suffered in the War of Ascension and he acknowledges that Emperor Lelouch was a horrible oppressive ruler. Despite what Lelouch had done, Suzaku believes Lelouch's death was tragic and horrific: Lelouch dying alone and terrified and his corpse torn apart by an angry mob.
- In A Night In The Sculpture Garden, Irene Adler arguably deserves her fate but it's hard not to feel at least a little bit of sympathy for her.
- In The Lion King II: Simba's Pride, Nuka, The Un-Favourite, mostly just wants his mother to appreciate him. In the end, he dies trying to get her attention and fails even at that. He spends his last breath apologizing to Zira for failing, his death prompting one of the only displays of love and affection that Zira probably ever showed him.
- Kadaj from Final Fantasy VII: Advent Children, whose main motivation was to be with "mother". He's at least welcomed into the afterlife by Aerith's spirit.
- Kung Fu Panda 2:
- Lord Shen. After a very miserable and empty life, he finally faces the warrior destined to defeat him whose entire species he tried to destroy... and the warrior has found inner peace, and doesn't want revenge. He cannot grasp how that is, how he could be free of all that pain, and tries one last time to kill him... only to accidentally kill himself. But he accepts it gracefully, because death is the only peace he could find.
- Also, the Boss Wolf. He follows Shen's orders without hesitation or mercy, but when Shen orders him to fire the cannon at the heroes, not caring that their own soldiers would be killed in the crossfire, Boss Wolf refuses. Enraged, Shen strikes Boss Wolf with his throwing knives and fires the cannon himself.
- While Cobra Commander was always an ineffectual coward in G.I. Joe: A Real American Hero, one can't help but feel for him in G.I. Joe: The Movie where he is lying on the ground, in agonizing pain, having been exposed to virulent spores that are mutating him into a snake, and slowly losing his mind.
- The Princess and the Frog: Dr. Facilier spent nearly the entire movie trying to kill Big Daddy and enslave the souls of the entire city of New Orleans as a goodwill payment to his "friends", and mode-locked Naveen into a frog, but the manner of his demise is rather tragic and horrifying. He is, rather graphically, dragged into Hell by his shadow, screaming and begging the entire time. It's so bad that Tiana, whom he just put in a Lotus-Eater Machine and is the indirect CAUSE of his death, can only watch in abject horror.
- In the Fantastic Mr. Fox, all the animals are saddened by the death of Rat, even Fox himself (who dealt the killing blow), despite his being the traitorous head of security for farmer Bean. Rat did manage to come to his senses in his few final moments when he revealed that he had turned traitor because he had become too addicted to the apple cider of Bean.
- Wreck-It Ralph: King Candy/Turbo's death. Granted he is an evil selfish asshole that only cares about himself but watching him fly into the coke volcano panicking while an epic farewell version of his theme plays in the background might get you to have a little sympathy for this Disney villain.
- Prince Hans in Frozen does things that are inexcusable, but the book A Frozen Heart delves more into his Dark and Troubled Past and his Freudian Excuse. His father is an extremely stone-cold, tyrannical and brutal dictator who favors his older sons but saw his youngest son as a "weakling" for not approving of his family's more violent methods of controlling people, so he allows them to harass and torment their youngest brother. Hans' journey to Arendelle wasn't even his idea, but his only kind brother Lars suggested marrying Elsa as a means of finding a new home. Ironically, Hans let his issues with family and desire to earn his father's respect make him do things he would have vowed to never do, namely take advantage of Anna's feelings for him and try to murder Elsa. As he is being sent back, it's clear to anyone who read the book that he didn't start out a villain, but his actions have painted him a criminal and sent back to the Hell he became too desperate to escape. His most recent appearance in the franchise, in Frozen Fever, we see him miserable in his punishment. He started out as a man who wanted to escape his horrible life to live a better one, but ended up as a villain who was willing to become just like the people he tried to escape, and if he never returns, he can never redeem himself.
- The witch named Agatha Prenderghast Used to Be a Sweet Kid who, like Norman, happened to have the ability to speak to the dead. She cursed the zombies in revenge for killing her only for being different. She became so obsessed with making the townspeople pay for what they did to her that she completely forgot about the people who loved her and she almost completely lost herself in her rage. When she is finally able to find peace with the help of Norman, Agatha Disappears into Light to move on to the afterlife upon realizing that the only thing she really wanted was to see her mother again after the townspeople separate them.
- The Judge (as well as the other zombies) have come to regret their actions over the hundreds of years they've been dead. When Aggie is finally at rest, they Disappear into Light to move on to the afterlife as they look scared and regretful.
- King Kong (1933) and all of its adaptations give sympathy to the ape once he's dead with the final line, "Twas beauty that killed the beast."
- Pirates of the Caribbean
- Pirates of the Caribbean: The Curse of the Black Pearl: Barbossa falls with the final line "I feel... cold..." and mournful violins play as his crew realize they're no longer cursed- but also no longer immortal, and they're immediately taken into Navy custody to be executed by hanging.
- Pirates of the Caribbean: At World's End gives us one for the Kraken, whose massive corpse stranded on a beach gets Captains Sparrow and Barbossa (both back from the dead) musing sadly about the end of an era it symbolizes, as well as for its master Davy Jones, stabbed through the heart and brokenly whispering the name of his lost love before he falls over the side of his ship and disappears into the maelstrom below.
Davy Jones: Calypso...
- Spider-Man Trilogy:
- Even if he is sadistic and self-serving, the downfall and eventual death of Norman Osborn/Green Goblin from Spider-Man can draw comparisons to that of Macbeth. He even accepts his fate, but not before making a final request to Peter Parker/Spider-Man.
Norman Osborn/Green Goblin: Peter...don't tell Harry.
- Dr. Octopus has a similarly tragic demise in Spider-Man 2. He never wanted to be evil to begin with, but his tentacles took the better of him. He even shows an epic defiance of his evil ways before choosing to drown with the fusion reactor to save New York from meltdown.
Dr. Octopus: "I will not die a monster!"
- Even if he is sadistic and self-serving, the downfall and eventual death of Norman Osborn/Green Goblin from Spider-Man can draw comparisons to that of Macbeth. He even accepts his fate, but not before making a final request to Peter Parker/Spider-Man.
- Hook gets this in his last moments, before the Lost Children wind up chasing him into the square where the Croc falls on him. Hook kind of spoils it, though.
- The American dub of The Return of Godzilla has Raymond Burr reflecting on how this trope applies to Godzilla.
- In Godzilla vs. Destoroyah, it's played again, this time far more successfully, with even several human characters who had dedicated their lives to beating Godzilla openly weeping at his demise. By now, he's a bit of an Anti-Hero, though.
- The oft-maligned 1998 American version also has a strong influence of this at the end.
- It goes all the way back to the original 1954 film; it's quite difficult to watch the beast in such pain as all the skin and flesh is ripped off its body, especially since the film shows that Godzilla is a Tragic Villain, and is as much a victim of the atomic bomb as everyone else.
- In the 2014 film, it's hard not to feel a bit sorry for the Mutos when the mother is mourning the death of her babies, especially when we see them meet and the father feeds a nuke to the mother and they nuzzle a bit before making the nest. The mother's anguished vocalizations manage to convey the message perfectly.
- Kill The Irishman. Real life Irish mobster Danny Greene tries to make peace with the Mafia and get out of the gangster business to retire in Texas. But the Mafia wants his head. The orphan who had a tough life is eventually killed with a car bomb, still Defiant to the End when he sees his killer point a gun finger at him.
- The Lord of the Rings.
- The series frequently shows Gollum's sympathetic side. His death is played for tragedy as he finally gets his greatest desire, only to be destroyed by the attempt.
- Wormtongue finally turns against Saruman and still gets shot by Legolas. This is after a My God, What Have I Done? moment upon seeing the Uruk-hai, and without his involvement in the Scouring of the Shire from the books, which is what actually gets him killed in them.
- In The Mummy Returns, Imhotep is abandoned by Anck-Su-Namun — for whom he essentially damned himself in the first place — as he is desperately clinging to a ledge. For a moment, he can only stare at the O'Connells — Evie having just rescued her true love, Rick, from the same situation — with a look of absolute, crushing despair. Then, with nothing left to live for, he lets go of the ledge and allows what looks like the souls of the damned to drag him into the precipice. The novelization takes it even further. Rick, despite himself, actually tries to save Imhotep from falling into the abyss. Imhotep still lets go of the ledge, but not without a few parting words acknowledging that Evie and Rick's love for each other was the real deal.
- Blade Runner: The death of Roy Batty, leader of the rogue replicants. From his Tannhäuser Gate death speech: "All those... moments will be lost in time, like tears... in rain. Time ...to die." And one dove rises.
- X-Men Film Series:
- Senator Kelly goes through absolute hell in X-Men and renounces his anti-mutant beliefs before dying.
- In X2: X-Men United, halfway through her death scene, the mind-control serum wears off and Deathstrike is allowed a few tragic seconds of clarity to realize where she is and what's happened to her; the look on her face says it all.
- In X-Men: Apocalypse Angel is the only one of the Four Horsemen killed in battle. Immediately afterwards, Apocalypse dismisses him as weak. This prompts Storm to realise that Apocalypse sees them as little more than minions, and pull a HeelFace Turn.
- Khan, Star Trek II: The Wrath of Khan. It is absolutely tragic - a man who could've achieved so much, reduced to being so blinded by hate that he's willing to die just to see Kirk die with him, largely because of the death of his wife between his last appearance in Space Seed and this movie.
- Shinzon from Star Trek: Nemesis. While not the best Trek villain, there's no denying that Shinzon's life sucked. He was created solely to be a tool of war, and through no fault of his own, he was eventually condemned to a lifetime of back-breaking labor in a hellish mine (while a child, no less). And even though he managed to overthrow his captors and the entire Romulan leadership a decade later, his engineered lifespan ensured that he had a very short time to live. In short, he lived a short, violent, brutal life, and never really had any chance to know love or happiness.
- The Penguin in Batman Returns. Even though he was a hideous psychotic sewer-dwelling monster, who spends his last few moments hating and hated and trying to take Batman with him, he also comes off as quite pitiable, and his burial at sea by his own beloved penguins actually comes across as rather moving, reminding that they were the only ones who were there for him. It all has to do with his poignant backstory and very wretched life which is summed up in this funeral so much that he is perhaps one of the evilest examples who is a Tragic Villain and makes this work.
- Ironically subverted in Hitchcock's Strangers on a Train. Magnificent Bastard Bruno is dying, and for a second it seems like he is going to admit his guilt; instead, he uses his last breath to further accuse the protagonist in front of the cops.
- The eponymous character of Blacula. After watching his beloved Tina - the reincarnation of a woman he's waited centuries to see again - get staked through the heart, he deliberately walks out into the sunshine, killing himself.
- Farmer Vincent who owns Motel Hell spends his last moments lamenting about his hypocrisy in preparing sausages made out of the human flesh of his victims... which in a humorous subversion turns out to be because of using preservatives.
- Calvera in The Magnificent Seven goes out trying desperately to understand why. Much of the pathos comes from Eli Wallach being just that good.
"You came back. A man like you? Why?"
- The death of Riley Biers in Eclipse. In his final moments, he calls out for his lover, Victoria, only for her to ignore him.
- Star Wars:
- The Rancor from Return of the Jedi. A dancing girl and a guard already had the misfortune of being its lunch. Luke has to work hard to avoid being torn apart by this hulking beast, and the spectators are very surprised when he manages to kill it. Then the rancor's keeper bursts into tears and has to be led away.
- HAL 9000 in 2001: A Space Odyssey. Despite being an apparently cold, logical computer AI who was willing to murder the crew of Discovery One, it becomes apparent why he did so: He was afraid. He did not want to be reprogrammed for making an error, which would essentially kill him. In the end, he is lobotomised while pleading for his life with the sole survivor (David Bowman), who ignores him. "Stop, Dave. I'm afraid. I am afraid, Dave. Dave... My mind is going. I can feel it. I can feel it..."
- The Stephen King movie Sleepwalkers looks like it's building to this, with the titular soul-sucking cat monsters constantly stalked by their weakness, and they're possibly the last of their kind. The young male Sleepwalker reads poetry describing their plight in class and seems to be falling for the female lead. A redemption plot looks all but guaranteed... And then when he tries to eat her soul, all the drama around whether or not he's falling for her vanishes and he becomes a gleeful monster with shocking speed.
- Vincent from Collateral gives a rather saddening Meaningful Echo just before he dies at the end of the film.
"Hey Max... A guy gets on the MTA here in L.A. and dies...think anyone will notice?"
- Sadako Yamamura, the Designated Villain from The Ring series, suffers a lot even before she becomes a villain. She is raped in the novels, lost her mother in both continuities, beaten to death by angry actors, and then she bonded with her evil twin and kills all those who harmed her before, including her own innocent boyfriend, before being tossed down the well by her stepfather.
- In Ring 2, Sadako appears before Mai Takano and Yoichi Asakawa as a ghost, asking why they can escape the well and yet she cannot, before allowing herself to fall back down into the well for eternity.
- Samara Morgan, the American version of Sadako in the American version of The Ring, suffers a lot too and is thrown down a well by her adoptive mother. This doesn't help, since her biological mother tried to drown her as a baby. And then she gets trapped in the well again at the hands of Naomi Watts.
- James Bond:
- Die Another Day: In-Universe; Bond experiences this when he sees Miranda Frost's corpse even though he had tried to kill her the instant he had learned that she was the traitor at MI-6.
- Skyfall: Raoul Silva is a former MI-6 agent, who was tortured to the point of severe facial deformity and hinted-at PTSD to keep their secrets. M (who left him for dead) admitted he was a "brilliant agent," and he himself has pulled a Not So Different with James Bond. At the end of the movie, M has been mortally wounded, and Silva begs her to put the same bullet through their heads to end both their suffering.
- In The Faculty, Casey kills the alien queen, Marybeth. As she is dying, he softly tells her, "You wouldn't have liked it here anyway.", acknowledging that — despite being a monstrous parasitic alien — she was just another outcast trying to find her place.
- In Law Abiding Citizen
- Aimes participated in a burglary. The plan appeared to be that his partner, Darby, would knock the adult occupants of the home to the floor with a baseball bat, then Aimes would handcuff them and then throw valuables from the home into a bag. Darby kills two people during the burglary while Aimes watches in horror and protests. Due to some legal technicalities and deals, Darby gets off easy while Aimes is executed. Aimes' last words: "What I did that day was wrong. But I'm not the one who killed those people. You're executing the wrong guy."
- Clyde Shelton, the man whose wife and daughter were murdered by Aimes's partner, Darby. Beginning as a combination Woobie, Destroyer of Worlds and Well-Intentioned Extremist, Shelton quickly jumps off the slippery slope and has no doubt crossed the Moral Event Horizon by the movie's end. Despite how far he sinks, though, Shelton never fully loses the sympathy points gained from his family's murder, and even shows remorse for his crimes. In the end he faces death with dignity, sadly looking at the charm bracelet his daughter made for him in the beginning of the movie, seconds before being killed by one of his own bombs.
- The death of Prince Nomak in Blade II, who was driven to kill his father out of revenge for making him the first Reaper. In a final battle, he is stabbed in the heart and chooses to drive the blade in further to end his suffering. Tellingly, he does so with a smile.
"Strange It hurts It hurts no more "
- In Alien: Resurrection, for all the murderous havoc the Newborn and it's entire race caused for Ripley, she's visibly sorrowful about having to kill it (and in an indirectly torturous manner at that).
- Willie Lopez and Carl Bruner in Ghost. The scenes of them being literally dragged into the netherworld (not to mention what is probably waiting for them once they get there) are pitiful and terrifying.
- It's hard not to feel a little sorry for the Emperor in Legend of the Black Scorpion when he realizes he was just another pawn in the Empress's plan, and accepts death at her hands because "if it is your will, how can I refuse?" He dies in her lap.
- Subverted in Scream 3 with the movie's Ghostface Roman Bridger. While Ghostface is dying, Sidney holds his hand because he's her lost brother. Barely a minute later he gets up to kill them all again just when they were sure he wasn't superhuman. Slasher Movie psycho killers have to be shot in the head to put them down.
- Dr. Elsa Schneider in Indiana Jones and the Last Crusade. Indiana attempts to save Elsa when she causes a Cataclysm Climax by trying to steal the Holy Grail. He manages to grab her before she falls into a pit; however, her obsession with the grail leads her to reach wildly for it. Indiana tries to hold on, but her hand slips from its glove and she falls to her death. After escaping the temple, Indiana looks back with an expression of regret that he couldnt save her life. His father shows less sympathy when he says, "Elsa didn't believe in the grail. She thought she'd found a prize."
- General Garza from The Expendables, who is killed as he undergoes a HeelFace Turn and stands up to the true Big Bad, Munroe.
- Viktor Cherevin from Jack Ryan: Shadow Recruit, especially when you find out that he has less than a few months to live due to his alcoholism.
- General Zod in Man of Steel. After losing everything he had due to his refusal to coexist with humanity, he soars across the Despair Event Horizon and commits Suicide By Superman by forcing Superman into a situation where he has no choice but to kill Zod. After his death Superman breaks down out of remorse, having clearly wanted to find a peaceful solution.
- Andrew from Chronicle. Being subjected to his Drunk Father's constant abuse everyday, his neglectful cousin Matt paying little attention to him until it's too late to save him, constantly being bullied by everyone in his school, once he gets telekinetic superpowers you can only imagine what's on his mind. Needless to say, when the time comes for Matt to put him down before Andrew could destroy Seattle, he was extremely reluctant to do so.
- In Peter Pan, at the very end, Captain Hook has just found himself right over the water, dangling above the crocodile with the last remnants of his fairy dust magic. Desperate to live, he starts thinking of all manner of things that make him happy while the Lost Children and Darlings repeatedly cheer "Old, alone, done for" to bring him down. Then, finally, Hook, sounding horribly depressed and weary, begins to repeat their chant, stops his flailing, and goes straight as he allows himself to fall into the mouth of the crocodile.
- The Saeki Family in the Ju-on and The Grudge, or at least Kayako, Toshio, and the cat Mar, who were all murdered by Kayako's husband Takeo under the false assumption Kayako was having an affair. Consumed by their own rage, they now haunt their former home and stalk and kill anyone who enters.
- In Run All Night, Jimmy Conlon kills Shawn Maguire, his old friend, and he lets him bleed out in his arms.
- In a way, as everything Sheriff Teasle from First Blood tried to do was to prove what Korean War vets are made of after being shunned for so long and to uphold the law in his duty as a policeman, yet now he's wounded in a pathetic state and is about to take more flak then he's ever before imagined.
- The death of ruthless railroad tycoon Mister Morton in Once Upon a Time in the West. An old crippled man who just wanted to see the Pacific Ocean before dying, Morton was willing to have Frank kill anyone who impeded his train's progress. After receiving a mortal wound in his duel with Cheyenne, Morton dies struggling to reach a puddle as a substitute for the Pacific while Frank looks on impassively.
- The Hunger Games:
Cato: Oh no, I can still do this. I can still do this. One... more... kill. It's the only thing I know how to do... to bring pride to my District.
- Cato. In the book, he's portrayed as a psycho Blood Knight who enjoys killing other tributes right down to when he dies. Here, he's more or less the same... until he's about to die. We then learn that his motives were to bring honor and respect for him and his District. He was also a career tribute, meaning that he was trained to kill from a very young age, and likely had no choice in the matter. Killing was all he knew. Combining all of these, plus his behavior at the end, implies that he was craving respect and recognition from people, which, in turn, implies that he was abused, neglected, unappreciated, ignored, or possibly all of the above. This may show that he feels the only way to be loved is to win. What's even sadder is, that assumption may have been true.
- Foxface wasn't really a villain in the book, mostly just being a parasite on the Careers, stealing their food and generally being sneaky. In the movie, we have a scene between her and Katniss where they bump into each other while running from the slaughter at the Cornucopia, look at each other in terror for a second, then silently run off in separate directions. This makes her seem a bit more like Katniss herself. Katniss even seems glum when finding out that Foxface is dead, and from a rather random death too.
- As in the original book (and possibly even moreso here), Glimmer in her death scene.
- To a certain extent, Seneca Crane. The character seemed to possess a certain degree of honor and fair play judging by his awarding Katniss points and there's something poignant about the scene where he's given a Sadistic Choice wherein his death occurs either way - especially since, like most Capitol citizens, he appeared to be more conditioned into his way of thinking than genuinely evil.
- Most of the Corleone family go out this way in The Godfather:
Vito: *crying* Look at the way they massacred my boy...
- Sonny Corleone in Part I, particularly with Vito's and Tom Hagen's reactions.
- Don Vito goes out with a smile playing with his grandson in the backyard of his estate as if he were any other grandfather.
- In Part II, we have Michael coldly telling Fredo "You're nothing to me now... You're not a brother. You're not a friend. I don't want to know you or what you do" as Fredo begs and weeps for forgiveness, right before Michael gives the order to kill him(delayed until their Mother's death). While they apparently make amends at their Mother's funeral, he silently affirms his previous order to Al Neri. Further reinforced by the flashback immediately after Fredo gets murdered, in which Tom Hagen and Sonny criticize Michael for opting to join the Marines instead of following in his father's footsteps; Fredo is the only one who supports him.
- Michael Dying Alone right after losing his daughter in Part III.
- The Professor's death scene in The Bourne Identity. Despite trying to kill Jason Bourne seconds earlier, our hero is horrified to realize he's another Treadstone agent. The audience already knows this, which may fatigue them with exposition. The screenwriter avoids this by injecting humanity into him, so instead of a steely eyed assassin, we meet a very human figure. Bleeding to death slowly, he begins to seemingly babble as Bourne tries to interrogate him, asking Bourne where he comes from, and darkly laughing about their terrible headaches— a result of their mutual behavioral conditioning. In fact, he is not babbling, but seeking commonality in his final moments. Near death, he looks down at his own wound, turns to Bourne and moans his haunting final words, "Look at this. Look at what they make you give." The scene sets a tone for the rest of the movie series. It would initially seem to be about the Professor's lost life, but over the course of the trilogy, with the eventual losses Bourne will endure, the audience sees that he's really talking about his sacrifice of his humanity to his government, and is echoed in the final movie as Jason Bourne's last line.
Jason Bourne: Look at us. Look at what they make you give.
- Snow White and the Huntsman:
- Ravenna's death is played sympathetically, as she is shown to be a Tragic Monster. Once Snow White stabs her, she cowers in a corner to die slowly. Snow stays with her as she does.
- In the sequel this goes double for Ravenna's sister Freya. The climax reveals that Freya's villainy was All for Nothing, that she had been duped by her sister and she dies saving the members of her army. Eric and Sara both look sad when she finally passes.
- In I Shot Jesse James, the death of outlaw Jesse James is treated as a tragic occurrence and an untimely end for such a legendary bandit. His death hangs over the rest of the film and the guilt of the action haunts his killer Robert Ford, who was Jesse's best friend and saw killing him as the only way to escape the life of an outlaw.
- Deep Red: Carlo had to live his whole life depressed and haunted by the memory of his beloved mother stabbing his father to death which meant that the cause of his trauma was also his only emotional support in the world. He covered up her crimes even while she threatened the life of his friend and felt so bound by his feelings for her that he also tried to kill Marc. After his awful end (getting his head crushed by a truck's wheel) a flashback scene to the night of his father's murder shows a horrified little boy who got traumatised for life.
- Ted Bundy: A rather bizarre example, with Ted Bundy's execution being treated as a tragic event despite all his actions up to that point earning him no sympathy whatsoever.
- Black Panther (2018): Even after everything he's done, Killmonger's tragic backstory earns him a quiet death, watching the Wakandan sunset with T'Challa. T'Challa even offers to heal him, but Killmonger refuses, asking T'Challa to bury him in the ocean alongside the slaves who jumped from ships in the Transatlantic Slave Trade.
- This is ultimately how A Series of Unfortunate Events ends, when Count Olaf is Impaled with Extreme Prejudice by a harpoon gun by Ishmael. By this point he has lost: his true love, friends, co-workers, parents, and his last chance at obtaining the Baudelaire fortune
- In Dragon Bones a minor villain is fed to a basilisk by a more major villain. Alive. This is a fate no one deserves. The heroes think so, too.
- Dragons of Requiem:
Solina: "I'm sorry. I'm sorry for how much I hurt you. All I wanted was to be with you here. I'm sorry."
- Queen Solina from Dragonlore. She spent all of her time slaughtering as many Vir Requis as possible as punishment for the amount of mistreatment she was subjected to by them growing up, not to mention that they killed her parents and banished her. It isn't until the final book where she realizes that she's just a sad woman who was blinded by her hatred, when all she truly wanted was to be with Elethor, her true love. Her final words really hammer it in.
- Prince Leresy Cadigus from The Dragon War was a pitiful Hate Sink who acted very haughty and believed he "deserved" everything he asked for, when he never earned it. He even put Rune and Tilla at risk in a desperate attempt to win his father's love again. When that fails, he lashes out at his father and brutally kills him, thus saving Rune and his sister Kaelyn and ending the trilogy's civil war. Shame he took a bullet in the process.
- Harry Potter
- Severus Snape. The subsequent chapter reveals that (despite his faults) he's not actually a villain. But Harry and the reader would have still assumed he was at this point, and it's still a sad scene.
- Barty Crouch, Jr. Sure, he became a death eater, but all he ever wanted was a loving father. Some fans thought that when he received the dementor's kiss, that his punishment was not only going too far, but also very sad, considering how neglected he was by his own father.
- Peter Pettigrew may be the most disgusting and loathsome character with no excuses, but you feel a bit bad that his own hand strangles him to death because of his one moment of mercy for Harry.
- Star Wars Legends:
- Grand Admiral Thrawn from The Thrawn Trilogy. "But it was so artistically done..." As the first major Imperial who was ruthless and pragmatic but not outright evil, he was always a fascinating character. Even his enemies couldn't help but admire him—an X-wing jockey once said, "I'd like to meet him, shake his hand. And then kill him, of course"—and his underlings adored him.
- Though the Revenge of the Sith novelization makes clear that Count Dooku is The Sociopath, you can't help but feel for him when seconds from death, he realizes everything he has done or accomplished, all his talent and power and intellect, has been used by Sidious to fulfill his plans with no regard for Dooku's wishes. Even worse, he realizes Sidious had always planned to kill and replace him. "Treachery is the way of the Sith."
- Martel's death in David Eddings' The Elenium fits the bill. After three books of playing Worthy Opponent to Sparhawk, he admits he knew Sparhawk was better all along, and both Sparhawk and Sephrenia forgive him and give him their blessings. Just for a minute, the guy who betrayed the entire Pandion Order goes back to being Sparhawk's brother in arms again.
Martel: You always said I'd come to a bad end, little mother, but you were wrong. This isn't so bad at all. It's almost like a formal deathbed. I get to depart in the presence of the only two people I've ever really loved. Will you bless me, little mother?
- The Belgariad:
- Zedar's fate in The Belgariad makes one almost feel sorry for the guy. Sealed up in the ground, forever? Yeesh. Worse when you consider that his FaceHeel Turn was a result of being forcibly turned by the Big Bad while trying to be the mole.
- Turned Up to Eleven in Belgarath The Sorceror when Belgarath as narrator almost casually notes that Zedar was always afraid of the dark.
- Speaking of which, said Big Bad also gets an Alas Poor Villain. Torak was a God of Evil, a Narcissist, and an utter bastard, but his death at the end, screaming for his mother as burning tears pour off his eyes after Garion takes away everything that matters to him? It's not pretty and it's acknowledged in-universe as such.
- The same could be said for Asharak, a high-ranking servant of Torak and manipulative bastard who messed with Garion for years, whose awful death will likely haunt Garion for the rest of his life.
- There's a retroactive example in The Malloreon. Taur Urgas, King of Cthol Murgos was a frothing madman, and was played as such in the The Belgariad. In The Malloreon he comes off even worse as it comes out what life in his home was like for his children. Garion notes when talking about the terminally-depressed 'Zakath that he would much rather be fighting Taur Urgas ("now there was a man I could cheerfully have gone to war with. He polluted the world just by living in it.") And then Eriond points out that "he was insane, Garion, and that's not his fault." At that point, all of Urgit's comments about his father's fits of madness and irrationality come back to you in a whole different light, as you realise that the man was genuinely clinically insane, and not merely Ax-Crazy, and never got any help for it.
- Zedar's fate in The Belgariad makes one almost feel sorry for the guy. Sealed up in the ground, forever? Yeesh. Worse when you consider that his FaceHeel Turn was a result of being forcibly turned by the Big Bad while trying to be the mole.
- Warrior Cats has a tendency to do this with most of its villains, due to its Grey and Gray Morality policy. Tigerstar, at least in the first series. Firestar notes afterwards that he could have been a great and noble warrior if he hadn't let ambition control him. The truly horrible death he suffered: being ripped open, and subsequently bleeding to death NINE TIMES.
- The reader might not feel this way, but Rafen from James Swallow's Warhammer 40,000 Blood Angels novels feels some sorrow when he sees the corpse of Sachiel. A nice foil to Sachiel's gloating over Rafen's (presumed) death.
- From Codex Alera, for all the horror she had caused, all the death and the near destruction of the world, the Vord Queen seems, in the end, to be a sad, lonely child seeking the approval of her father.
- Romance of the Three Kingdoms:
- Cao Cao gets a long poem on his death, daring anyone to criticize him.
- Smug Snake Yuan Shu dies as a result of some mixture of illness, starvation, and dehydration, all the result of his last botched campaign. His last words are a request for a little honey water for his throat, to which his chef replies that there is no water in the camp, save that which is tainted by blood.
- Many villains from Memory, Sorrow and Thorn by Tad Williams get this treatment.
Binabik looked at him curiously. The innocent can be molded, as those children were, but sometimes luck is granting that they can be molded back. I have little belief in evil beyond redeeming, Sludig.
- King Elias, despite playing the Unwitting Pawn and being a complete Jerk Ass throughout most of the series, reveals that all the evil he commits (and abets) started with grief over his wife's untimely death. At the very end, he begs to be killed so he won't become the host for the Eldritch Abomination that the Big Bad Storm King has become.
- Fengbald, the viciously amoral leader of Elias' army and the man Princess Miriamele was going to be forcibly married to, dies pitiably when he's caught in the trap of the Fake Defectors at the battle of the Stone of Farewell.
- Ineluki, the Big Bad himself, is revealed to have committed all the atrocities in his life out of love for his people and a desperate desire to lead them to salvation. In the end, this realization leads directly to his defeat.
Oh? The Rimmersman laughed harshly. What about your Storm King? What good thing could you possibly say about such a black-hearted hellspawn as that?
Once he loved his people more than his own life, Binabik said quietly.
- In Otherland, Tad Williams' next offering, the death of Corrupt Corporate Executive Felix Jongleur is suitably karmic as his creation, the Other, turns his worst fears against him. However, given the glimpses the reader's allowed to see of his upbringing in a Boarding School of Horrors and how his entire adult life has been driven by fear of the Anthropomorphic Personification of Death, it's hard not to feel sympathy for the poor tormented kid who grew up to be a bully himself, but died screaming in absolute terror.
- Dragonlance universe:
- A short story has Tanis and Flint kill a Black Mage who's been sucking the life out of people. After he's dead, they find out that he was doing it to prolong the life of his sickly son.
- Test of the Twins: the Archmage Raistlin Majere attempted to become a god by dethroning one of the current ones. He manipulated everyone around him, abandoning or killing them as soon as they stopped being useful, and, as shown in an alternate would, have not only succeeding but have DESTROYED every other god in the pantheon, leaving him sole ruler of the universe. However, he sacrificed himself to save his time-traveling brother, ex-friend, and one of the people he manipulated, because they showed him that he would destroy the world in the process of attaining godhood.
- Several villainous characters by John C. Wright are pitiable when they die:
- War of the Dreaming: Angelo Casselo, who knows he's nothing but a pawn in the game; and Manannan, alias Tom, a What Measure Is a Non-Human? who had been desperately playing both sides in an attempt to prevent his people being annihilated.
- Chronicles of Chaos: Grendel Glum, who, for all his monstrousness, is merely a lonely old man, and Echidna, who is killed in the middle of her Mama Bear rampage.
- Almost every half-blood villain in Percy Jackson and the Olympians gets this in the final book.
- Luke tries to kill the heroes multiple times and tries to help the Big Bad, Kronos, rise again (eventually hosting him in his own body). In the final chapters of The Last Olympian, he sees Annabeth bleeding, breaks free from Kronos's mind control, and realizes that he was fighting for the wrong side. He then kills himself to destroy Kronos, and it is indicated that he goes to Elysium in the afterlife.
- Ethan Nakamura fights in a battle to the death against Percy, and when Percy wins, he refuses to kill Ethan. Ethan repays him for this by betraying him and pledging himself to Kronos, enabling Kronos to rise again. Throughout "The Last Olympian", he is seen working for the Titans. Then, Percy convinces him to turn against Luke/Kronos, who kills him, earning him sympathy in the end.
- Silena Beauregard originally seems like a gentle, romantic daughter of Aphrodite. However, she is secretly a spy for Luke, and the information she has reported has lead to the deaths of many campers. When Kronos and his minions become responsible for the death of her boyfriend, she begins to think twice about her actions and eventually disguises herself as Clarisse, rallies the absentee Ares campers, and charges a Drakon, resulting in her death. Her secret - that she was the spy - comes out as she is dying, but the other campers remember her as a hero anyway.
- The Phantom of the Opera — Erik's death has this effect both on readers and on his fellow characters. Him being born disfigured and never being given a chance to live like a normal person, which was what he desired the most, led him to use his charisma and talents for evil because only there did he find acceptance and by the end he died happy that found at least some affection from Christine.
- In City of Heavenly Fire, Sebastian Morgenstern goes down quickly, but Jonathan, the good within him, arises, tells Clary how to destroy the Infernal Cup, talks about what might have been, and then dies.
- Robert E. Howard's Conan the Barbarian
- In "The Slithering Shadow", Thalis tortures Natala, but after the titular shadow swallows her up:
She shuddered. "She tortured me yet I pity her."
- In "Shadows In The Moonlight" — Shah Amurath
Olivia closed her eyes. This was no longer battle, but butchery, frantic, bloody, impelled by a hysteria of fury and hate, in which culminated the sufferings of battle, massacre, torture, and fear-ridden, thirst-maddened, hunger-haunted flight. Though Olivia knew that Shah Amurath deserved no mercy or pity from any living creature, yet she closed her eyes and pressed her hands over her ears, to shut out the sight of that dripping sword that rose and fell with the sound of a butcher's cleaver, and the gurgling cries that dwindled away and ceased.
- In "The Slithering Shadow", Thalis tortures Natala, but after the titular shadow swallows her up:
- In Dracula, Renfield's death invokes this trope. He's mostly unsympathetic for most of the novel—he nearly beats a man to death and attacks one of the protagonists with a knife—but when he realizes that Dracula had lied to him, he attempts to defend Mina Harker from him and is fatally injured because of it. The graphic description of his injuries doesn't help.
- In Skulduggery Pleasant: Mortal Coil, the death of the Russian assassin Tesseract. After being fatally injured by Lord Vile, Tesseract removes his mask and asks Skulduggery to help him get outside so that he can feel the sun on his face one last time. As they go, he talks about how he'll miss his cat, and how he has no regrets.
"I have a cat, you know. Back home. [...] She doesn't have a name. She is just Cat. She curls up on my chest whenever I sit down, and goes to sleep. I hope she doesn't miss me. I'm going to miss her."
- Mandrake is introduced in Duncton Wood three chapters in as a bloodthirsty, giant mole that later becomes an iron-fisted dictator. Then, in a quick moment of Rebecca's life, he scolds her for enjoying the snow and, after that, delivers a speech against the snow that's quite poignant considering his story. And when he finally dies, he does so half-mad from wandering the Ancient System for months alone, crying for his only daughter while being mercilessly beaten down by a revengeful Stonecrop.
- Sly Moorcock from Stark by Ben Elton is a ruthless billionaire who has no qualms about leaving Earth with the other billionaires and letting humanity die in the inevitable ecological breakdown. Yet he moves more and more into Anti-Villain territory as the story progresses, and shows himself in possession of both moral standards and the capacity to love, and when he commits suicide in the epilogue by throwing himself out of an airlock, it is just as sad as when one of the good guys die.
- In Azure Bonds, the red great wyrm dragon Mistinarperadnacles lays down her life to destroy the Darkbringer Moander. The heroes mourn her, and one of them, Akabar, notes that Mist's evil was fairly petty while she died saving the world from a Fate Worse than Death. He even suggests that the group's bard should compose a song about her.
- Aurora in The Dresden Files, the well-meaning but insane villain of Summer Knight:
'Wait,' she said, her voice weak and somehow very young. She didn't look like a mad faerie sorceress now. She looked like a frightened girl. 'Wait. You don't understand. I just wanted it to stop. Wanted the hurting to stop.'
I smoothed a bloodied lock of hair from her eyes and felt very tired as I said, 'The only people who never hurt are dead.'
The light died out of her eyes, her breath slowing. She whispered, barely audible, 'I don't understand.'
I answered, 'I don't either.'
A tear slid from her eye and mixed with the blood.
Then she died.
- In Good Omens, the demon Duke Ligur is doused in holy water in a booby trap set up by Crowley. He thoroughly deserved it, but for a demon, it's an amazingly horrible way to die, and his partner-in-crime Hastur immediately goes into Villainous Breakdown and attempts a Roaring Rampage of Revenge on Crowley, chasing him down a phone line.
- Phoena's death in Fusion Fire was so horrific that Brennen did his best to comfort her in her last moments, despite the fact that not only was she responsible for his capture by the Shuhr, but she also tried to have him and his wife essentially tortured to death.
- The third Safehold book, By Heresies Distressed, has this happen with Prince Hektor of Corisande. He's been beaten, he knows it, and he is preparing to negotiate terms of surrender with Emperor Cayleb. Before he can, however, he and his eldest son and heir are victim of an assassination that is blamed on Cayleb. Hektor, in his final moments, realizes that he truly loved his son, who had thus far been The Un-Favourite.
- In The Bartimaeus Trilogy, Faquarl achieves the vengeance he's been craving for 5000 years, and discovers that it doesn't bring him the satisfaction he wanted. Then he finds Bartimaeus sharing a body with a human, proving him wrong about the inevitability of conflict between humans and spirits. Bartimaeus narrates that he's never sure if, had he wanted to, Faquarl couldn't have killed them before they shot him.
Faquarl: Your discovery is remarkable. But it comes too late for me.
- In Death series: this has happened with some of the murderers after they get caught or killed. Portrait in Death has Eve and Peabody realizing that the murderer they caught wasn't greedy, vicious, or downright evil, just pathetic.
- Time Scout's Skeeter Jackson truly feels sorry for what happens to the enraged gladiator who spent the entirety of Wagers of Sin trying to kill Skeeter.
- Antrax in The Voyage of the Jerle Shannara was just following its programming. Its reaction as it slowly loses contact with the outside world and shuts down is as sad as it is necessary.
- The Aeneid: Most of the antagonists go out rather sadly. The standout may well be Mezentius, Nay-Theist, exiled tyrant, and brutal fighter whose disdain for the gods and vicious rule over his old city-state have brought him to Italy to fight as a mercenary. When his son and Morality Pet Lausus is slain, Mezentius goes ballistic, cutting down opponents left, right, and centre before being stopped by Aeneas; his Famous Last Words, wherein he refuses to pray and asks only that he buried by his son, are quite touching.
- Durza, the Shade from Eragon, surprisingly earns sympathy just before his death at the hands of the protagonist. While fighting off the Shade's mental attacks, Eragon accidentally breaks through into his mind and sees a quick succession of images from his early life, before he became a Shade. The man who became Durza was originally a young orphan named Carsaib who was taken in by a sorcerer and instructed in the art. When his master was murdered, the grief-stricken young man called upon powerful spirits to get revenge, but they proved more than he was capable of handling and possessed him. Durza was pure evil, but Carsaib was a tragic figure who made a terrible mistake and paid dearly for it.
- Of all the characters who are involved in the Final Solution of Timeline-191 — or at least all of the ones you get to know — only Hipolito Rodriguez is still human and moral enough to have a Heel Realization and repent of what he has done. It's the sincerity of his horror and repentance that evokes sympathy.
- From It, Patrick Hockstetter's death to some. Yes, he is a creepy and very disturbing sociopath who sees absolutely nothing wrong in doing things like suffocating his baby brother and killing animals for fun, but his death is so disturbingly horrifying and disgusting that it might be hard to feel any satisfaction over it.
- In The Stand, the death of Harold Lauder. Presented as a fat, sometimes disgusting social outcast who uses overly purple language at times, is insanely jealous of Frannie Goldsmith, incredibly hateful towards the Free Zone Committee (and Stu Redman in particular, whom he believes stole Frannie from him), pompous, contrary and argumentative, Harold is nonetheless a tragic figure: sadly used by the Big Bad, Randall Flagg, who takes advantage of Harold's weaknesses and literally leaves him to die by the side of the road with his leg shattered. Harold's final statement says it all: "I was misled."
- In The Dark Tower there is the death of Trampas, one of the Mooks guarding the Devar-Toi. He works for the Big Bad, but he's actually a pretty decent guy once you get to know him. It's made pretty clear that Ted really doesn't want to kill him and even yells at him to get out of their way, although he is forced to eventually resort to throwing a mind-spear at him, killing Trampas in the process.
- In Fate/Zero:
- Caster having a hallucination of Jeanne d'Arc reaching out to him while smiling and realizing just what kind of monster he has become before dying.
- There is also Kayneth's death, based on your definition of "villain" (he did kill Risei). It's hard not to feel a little sorry for him when he gives up the War to ensure the safety of the woman he loves, only to be ruthlessly gunned down together with her.
- The gamebook Search for Dinosaurs: A T-rex slowly starving in the aftermath of the meteorite fall is a rather pitiful sight, even if it tried to eat you previously.
- The Wheel of Time: Asmodean and Lanfear. Ishamael could possibly be considered an inversion, as he wanted to die, and being resurrected was his punishment by the Big Bad for his failures and insubordination.
- Kara no Kyoukai: Overlooking View has Kirie Fujou, who unconsciously uses her spiritual counterpart to drive other girls into suicide out of loneliness. When Ryougi kills her spiritual counterpart, Kirie says that the moment Ryougi killed her was the most she has ever felt alive. Feeling she has nothing to live for and wanting to experience death again, she commits suicide.
- There is also Fujino Asagami in Remaining Sense of Pain, although she's mostly an Anti-Villain. She's been raped, her own father has hired Ryougi to kill her, and she's dying a slow, excruciating death via untreated appendicitis. At the end of the chapter, she's crawling through rubble, weakly repeating that she doesn't want to die between bouts of vomiting blood.
- Araya Souren in Paradox Spiral. As he lays dying after Ryougi defeats him, Touko questions his obsession with the Spiral of Origin. Araya recalls his past and we see that witnessing endless death and tragedy has left him guilt-ridden over his inability to save the people around him in his years as a wandering Buddhist monk, so he decided to at least record their deaths and desperately attempted to find some form of meaning or purpose in them.
- Although the death of Bertha Mason in Jane Eyre leaves Jane and Rochester free to get married, it's hard not to feel for her, especially since her life has been so loveless and painful.
- The Lord of the Rings: Loathsome as Grima Wormtongue might have been, it's hard not to pity him when one sees the level to which he has been reduced by the time of his death.
- In The Doomspell Trilogy by Cliff Mcnish the death of the first book's main villain Dragwena in the second book is really rather sad. The way she dies is rather horrible as she attempts to revive herself but Came Back Wrong in a Body Horror way. She also dies being cradled by her mother and sister who love her deeply and mourn her death.
- At the end of The Spell of the Black Dagger, Overlord Ederd, having been restored to his throne, refers to Tabaea, the woman who overthrew him and seized control of the city and then died in a failed effort to save it (the city was saved, but not by her) as "that poor girl" and "poor little Tabaea." It is clear that he means it.
- Les Misérables chapter "Javert In Disarray" is all about this, as Inspector Javert is Driven to Suicide after his entire view of the world is destroyed by Jean Valjean saving his life.
- Not even an Ax-Crazy Jerkass like Cato deserves to be Eaten Alive by Mutts for over twenty hours in The Hunger Games.note
- Alfred Builder in The Pillars of the Earth, in a Big Bad Wannabe sort of way. He was a Big (Step)brother Bully to Jack and Martha, got Jack kicked off of the building site of Kingsbridge Cathedral, married Aliena out of spite just so Jack couldn't have her and treated her like crud, betrayed his stepbrother when he had the decency to hire him after all he did, and even tried to friggin' rape Aliena at knifepoint. However, he becomes a lot more sympathetic once you realize that, unlike Willaim Hamleigh or Waleran Bigod, he acted the way he did not because he wanted power or because he enjoyed it, but because his whole adult life he had to deal with one tragedy after another: his mother's death, his father favoring his stepson over him, the woman he loved turning down his marriage proposal, and his father's death. Everything he did was out of revenge for the world treating him awfully. Aliena even muses as he lays dying that he could have been a better, happier person had he just been nicer:
"She thought, as she looked into his eyes, that he had never been compassionate himself, nor forgiving, nor generous. He had nursed his resentments and hatreds all his life, and had taken his pleasure from acts of malice and revenge. Your life could have been different, Alfred, she thought. You could have been kind to your sister, and forgiven your stepbrother for being cleverer than you. You could have married for love instead of revenge. You could have been loyal to Prior Philip. You could have been happy."
- The Da Vinci Code: has Silas who spent all his life being treated as a monster and an outcast for being an albino, so much that the one time that someone showed kindness to him, he ended up joining his religious crusade out of gratefulness. While this led him to commit terrible crimes, by the end he went through a big My God, What Have I Done? moment where he prayed not for his life but for his adopted father's and died hoping to find piece and God's forgiveness in the end.
- mothy loves this trope, especially in the Evillious Chronicles.
- It is almost impossible to not feel sorry for Gallerian at one point or another. His entire family was murdered because he didn't want to work with MA. He honestly believes the Clockworker's Doll is his daughter. And, at his death, there's an image of him hugging his 'daughter'. And later on, it's stated that him protecting her from the flames was the only reason she didn't die.
- Lemy's death. Despite him being an Ax-Crazy Serial Killer Enfant Terrible, the lyrics really hammer in that he was just a kid.
Pierrot doesn't want to die! Pierrot doesn't want to die!
- The titular duke from The Lunacy Of Duke Venomania—despite everything he's done, it's hard not to pity him as he dies completely alone, abandoned by everyone; his harem, the woman he loved (realizing too late he loved her and being unable to voice it), and even the demon of Lust. He reverts back to the ugly appearance that caused him so much abuse in his childhood afterwards, too.
- Margarita Blankenheim gets this in Gift From The Princess Who Brought Sleep, with Elluka trying to stop her from committing her misery-induced suicide. Subverted when it turns out this didn't kill her after all, and Margarita's nature was much, much more sinister than originally thought.
- The music video to "Gods and Punks" by Monster Magnet. Sure, it leans heavily on parody ("Will destroy your world for food") but when in the end the brats kill the villain (who saw better days) with his own death ray, you shed a tear for him.
- In the biblical Books of Samuel, David's son Absalom rebels against him and is ultimately defeated and killed. When David gets the news, rather than rejoicing over the victory, he is devastated and mourns his son so intensely that his officers finally have to give him a What the Hell, Hero? for hurting his men's morale.
- Farmgirl and Goodwitch mourn Dark Lady's passing in the artwork for Kozmourning in the Yu-Gi-Oh! TCG. The scene resembles both a sorrowful Dorothy regretting having to kill the Witch and Luke Skywalker mourning his father's death.
- Makuta Krika in BIONICLE; he was the Noble Demon of the Makuta with a Monster Sob Story, who only went along with the plan of the Makuta of Metru Nui because he saw it as a "damned if you do, damned if you don't" scenario. He made a genuine effort to help the Toa (the heroes) at the end of the Karda Nui arc, and then, when he learned that the Makuta were about to outlive their usefulness, he tried to warn them, and was rewarded by slowly becoming so intangible that all of his atoms flew apart - the kicker of his death was that it was caused by his own power being forced out of control by his brethren, who thought he was lying.
- Subverted in Oklahoma!. Curly tells Jud that when he dies, people will cry for him despite being afraid of him prior to his death. When he actually dies, what's the first song that they sing? "Oh what a beautiful morning
" Foreshadowed in the Curly/Jud duet Poor Jud is Dead. Jud is really getting into this vision of how awful people will feel when he's dead, and Curly is echoing:
Jud: And folks are feeling sad that they used to treat him bad, and now they know their friend is gone for good.
- Romeo and Juliet
- Tybalt. After all, the hero had just murdered him for what had ultimately been an accident. As this is Shakespeare, the validity of this is really up to the director and the actor.
- Paris would also be a good example. He's often displayed in a negative light, but ultimately, is simply a man trying to woo a girl he's in love with in the typical fashion of that era, and he's killed while trying to arrest a dangerous criminal who had killed the cousin of the woman he loved, and, for all he knew, drove her to suicide.
- Javert from Les Misérables gets sent off after having his entire worldview shattered.
- Heathers: J.D. committed murder, and attempted to blow up his school. But it is clear that before Veronica, no one truly liked him, his father was cruel, and his mother killed herself in front of his eyes. And he ends his life taking his bomb from Veronica, admitting he is "far too damaged". Even Veronica, despite everything he's done, can't help but plead for him to stop.
- Played with in Wicked. Even as the rest of Oz celebrates Elphaba's death, Glinda can't help but bring herself to condemn her old friend. Of course, not only is Elphaba not the bad guy here, but she's not actually dead either - she's run off with Fiyero/The Scarecrow to live the rest of their lives in peace.
- Inverted in Hamilton, as it's the hero (Hamilton) who is killed, while the antagonist Burr is filled with regret and claims that "I survived, but I paid for it". Undercut by Real Life, of course, because Burr did some not-so-sympathetic actions afterward, including attempting to secede from the US.
- Higurashi: When They Cry: Takano ultimately is subject to this trope, left to run and fall apart emotionally in the rain in a scene mirroring her escape from her Orphanage of Fear, bloody and barefoot, left a gun with one bullet with which to kill herself, betrayed by all her allies, and ultimately left to have her grandfather's papers stomped on again, causing her to break down sobbing as her trauma catches up with her.
- Umineko: When They Cry: Beatrice falls in this trope. She starts the series as a witch who loves to kill Battler's family in the most horrifying ways, but in EP5 it's confirmed that she didn't actually enjoy doing this, and in EP7 you are shown just how Beatrice came to be. After she's broken, Bernkastel keeps playing with her.
- 'Dangan Ronpa'' frequently has this for its killers.
- Leon is taken to his execution utterly terrified, having killed Sayaka after her attempt to kill him (which, according to the manga, was an accident).
- After being convicted for killing Chihiro, Mondo is revealed to have accidentally killed him in a fit of rage. If the time limit ran out and Monokuma revealed everyone's motives, it would have revealed that Mondo's recklessness had been the cause of his older brother's death, a secret that would have caused their biker gang to fall apart. Mondo barely argues back and accepts his argument- the only reason he moved Chihiro's body was to keep his promise and ensure that no one found out Chihiro was a boy.
- Even Celeste, the most ruthless of the murderers in the first game, gets this. Despite Celeste unapologetically claiming to having killed Hifumi after manipulating him into killing Taka, simply to escape and live a life of luxury, Makoto notices that she's still scared at the prospect of her impending death, and it's up to the player's interpretation as to how much of her story was a lie.
- In the second game, Teruteru is revealed to have accidentally killed Byakuyanote , while trying to kill Nagito for two reasons. The first is because he thought Nagito was trying to kill someone, not realizing that Nagito wanted to get the killing game started by any means necessary, even at the cost of his own life. The second was because he was desperate to get home and look after his sickly mother.
- After Peko's plan to make Fuyuhiko graduate fails due to her being considered the murderer, Peko apologizes to the remaining survivors, asking them to forgive Fuyuhiko for causing the murder and not allow another killing. She has an emotional breakdown after Fuyuhiko's Anguished Declaration of Love, and dies protecting him when he's injured trying to stop her execution.
- Gundham willingly accepts his fate, saying that while he killed Nekomaru so that the class wouldn't starve to death, he's nothing more than a murderer, and it's strongly implied that he allowed himself to be caught so that the others wouldn't be executed.
- In the third game, Gonta is manipulated into killing Mio (who also gets a fairly heartbreaking death scene) by Kokichi, only to end up forgetting that he committed a murder as a result of accidentally putting the wires in the wrong sockets. For most of the trial, Gonta honestly believes that he's innocent, and his death is one of the saddest executions in the game.
- Godot's defeat in Phoenix Wright: Ace Attorney: Trials and Tribulations could count, judging by how he was desperately trying to repay his debt for Mia Fey, for whom he blames himself for her death and has been taking it out on Phoenix for his failure to stop the murder back in the second case of the first game. It's not until Bridge to Turnabout that he was finally ready to forgive him.
- Acro's defeat as well in Phoenix Wright: Ace Attorney: Justice for All, with his remark (that you have to interpret for Regina) about how he wanted to stick around, which is why he didn't kill himself or turn himself in despite being overwhelmed with remorse for accidentally killing Regina's father. He's worried that he might be in prison or executed by the time his brother gets out of his coma.
- Caster in Fate/stay night's "Unlimited Blade Works" scenario. Yes, she captures and tortures Saber, holds Taiga hostage, and is responsible for many a Bad End in Unlimited Blade Works, including one where she orders Shiro's friend, Issei, to kill him. Yet her last moments were so touching, it almost made you forget all that.
- Kirei Kotomine in Heaven's Feel, even more so. His actions in the route, and the backstory it reveals, does an impressive job of building sympathy for him, considering that he lives to see others suffer and is actively trying to destroy the world. Seeking the reason for his twisted existence, he died without regret. No wonder Shirou realized that he liked Kirei.
- Zouken Matou. It's difficult to feel sympathy for the monster he's become, but you might just pity the idealistic Zouken Makiri, who kept seeking immortality so that the woman he loved wouldn't have died in vain.
- Ilya, who in 'Fate' was a psychopathic monster at worst, appeared in 'Unlimited Blade Works' long enough for a finale with backstory that managed to make her sympathetic without even giving away her whole Freudian Excuse (which was saved for 'Heaven's Feel'). And Berserker, already Deader Than Dead from his Self-Destructive Charge, managed to stand long enough to give her comfort before both died.
- Doki Doki Literature Club!: As horrifying as her actions are, Monika is still worthy of pity. She's gone utterly insane due to her status as a fictional character, and on top of that, she doesn't even get a chance to romance the player character, meaning her only purpose in life is to be a side character. It doesn't excuse the lengths she went to to rectify this, but it's understandable how she ended up this way. And, in the end, she saves you — proving that when she says she loves you, she means it.
If I don't know how to love you... I'll leave you be...
- In The Order of the Stick:
Elan: I know now that we were never going to be family, but...he didn't deserve this!
- Miko Miyazaki's slide from holier-than-thou Knight Templar to a Tautological Templar has her murder her lord, lose her Paladin powers, and accidentally kill herself in fulfilling what she had decided was her divinely ordained destiny. The ghost of her order's founder tells her that her efforts were... adequate... but not worthy of redemption, which she accepts with uncharacteristic grace as she dies. It's still debated whether she deserved it.
- In strip 830, it's really hard not to pity Tsukiko — an unrepentant Card-Carrying Villain who sold out her own city to Xykon — when Redcloak usurps control over her wights, who she'd treated like her own children, to prove that undead are little more then automatons for necromancers of any stripe. And then he has them drain her to death. And then eat her. She was a sick, twisted, self-confessed necrophiliac who was obsessed with Xykon because every living person she ever met in her entire life treated her like crap. What puts her solidly in Alas Poor Villain territory is that she really and truly loved him, and only died because she discovered concrete proof that Redcloak is manipulating Xykon, and that the MacGuffin they're after won't get Xykon the power he wants. The point really gets hammered home when the only person to mourn is the Monster in the Darkness, who points out that in the end, Tsukiko just wanted to be loved.
Demon-roach: So what? Who cares?
Monster in the Dark: Exactly. That's why I'm sad.
- Nale's death in 913: Independent has caused some of these reactions. Nale is a petty, selfish mass-murderer, but hearing his anger about being treated like a tool by his father, and refusing his father's help to his face shows that he has balls, only to get stabbed by his own father. Plus Elan's reaction...
Haley: Elan, he...kinda did. He was a terrible human being.
Elan: Yeah, but- how could I be mad at him? What if it had been me? Raised here? Would I be a jerk, and he be the hero?
Haley: I...don't know.
- Subverted when a reanimated Crystal is dumped into lava: three panels of silence, followed by brunch.
- Whenever Oasis dies in Sluggy Freelance, it's treated with sadness, even when she's been in full-on Ax-Crazy, Stalker with a Crush mode, since we know she's only like that because Dr. Steve Brainwashed her. However, as Oasis becomes more heroic and we learn she'll always come back from being killed, this has faded.
- Violent Glaswegian Dougie in What the Fu suffers a breakdown from the revelation that he's not actually Scottish. Zac almost feels sorry for him, except he's "still a murderous psychotic bastard".
- Vriska Serket, who had spent the entirety of Act 5 Act 2 getting closer to John and finally admitting that she wanted to try living a normal life. She was killed by Terezi in order to prevent her from fighting Jack, which in an alternate timeline got everybody except Vriska and Aradia killed. Her final message? Telling John that if and when they finally do meet, she'd like to go on a date.
- Courtyard Droll, Jack's clueless underling who fails at being evil, which gets his superiors pretty annoyed with him. When he finally manages to follow one of Jack's orders to the letter (Jack had ordered him to kill Jade, something Jack himself couldn't do due to his Undying Loyalty from Bec's prototyping), Jack snaps and kills him. Thankfully the Scratch brings him back. Sort of.
- Snowman is a Jerkass, but it's hard not to feel bad for her when the Doc Scratch-influenced Spades Slick shoots her dead at the end of Act 5, especially since she had just saved his life a few moments before. Furthermore, she requests and welcomes her own death as an end to her eternal servitude to Lord English.
- Ephsephin from Unsounded, an Ineffectual Sympathetic Villain who suffers more and more abuse as the story goes on. He becomes even more sympathetic when Word of God says he was a failure at life who was obsessed with over how he couldn't provide a better life for his mother. The only reason he signed up with Starfish was to get a big enough payoff so that she wouldn't have to keep breaking her back working. After he gets grievously wounded by Jivi and begs Starfish for a doctor, Starfish merely smiles, then bashes his head in with a whiskey bottle.
- Tobun in Penny Arcade's Cardboard Tube Samurai storyline, is implied to have become a Death Seeker after being compelled to commit atrocities. Fighting the CTS hand to hand, his last words are "before this moment, did I ever see the world?"
- Dragon Ball Multiverse: The first Cell Jr's death by his own father's hands. Especially after he had a Hope Spot of becoming more powerful.
- At the grand finale of Errant Story, Ian just keeps repeating "I just wanted to help." Despite a personal body count in the thousands, he's quite serious. However, it doesn't keep him from getting his brains blown out.
- Apple Bloom in Moody Mark Crusaders. Even though she's a jerk, it's hard not to feel sorry when she's Taken for Granite. She gets better though.
- Kalki in Drowtales spends the majority of her screentime either acting like The Fake Cutie or inflicting serious harm or brutal deaths on other characters, including stabbing the hand of her own half-sister and nearly killing her by chopping off her arm the very first time they meet, but the way her mother Snadhya'rune, whose neglectful parenting was at least half the reason she became as twisted as she did, coldly kills her and tells her she has outlived her usefulness firmly puts her into this.
- Happens quite often in Survival of the Fittest:
- Bobby Jacks' death, committed after realising the path he took. Read it here.
- Laeil Burbank goes out with a fairly tragic death, accented by how violently and sadistically she received her fatal injury and how she was almost saved. Found here.
- Clio Gabriella gets a fairly touching send-off, dying in her boyfriend's arms while she begs for him to save her after being shot. Again, readable here.
- In the Global Guardians PBEM Universe, the villain Hardcase was generally thought of as a brutish, selfish thug who liked to beat up women for fun, drank too much, and was generally a sleaze. And on September 11, 2001, he gave his life by using his superhuman strength to save people from the collapsing North Tower of the World Trade Center. The heroes not only campaigned to get him a posthumous presidential pardon, they sprang for a funeral the likes of which are normally reserved for deceased presidents and popes.
- CT in Red vs. Blue (no, not the one from Season 7, the real Freelancer who the Rebel Leader took the identity of) was never really a villain in the first place, but instead ended up becoming a Hero Antagonist to try and take down the Director. Her reward for trying to do the right thing? A throwing axe to the chest which mortally wounds her, causing her to die in her lover's arms.
- The Director also got a moment like this in the finale of Season 10, when he realised he should have spent more time looking after his daughter Carolina, realises that he has been chasing at ghosts futilely for several years, asks Carolina for a pistol, makes peace with her and F.I.L.L.S and then is implied to commit suicide.
- Parodied in Part 3 of the Ben Mc Yellow series. Despite being a gleefully psychotic Blood Knight with absolutely no sympathetic qualities, when fatally wounded, Lord Sword slowly falls to his knees with great dignity while mournful music plays. Then when his body finally hits the ground, he instantly vanishes with a fart sound effect.
- Scion of Worm was unquestionably a sadistic, Omnicidal Maniac, but the way that Taylor defeated him by taunting him with the death of his counterpart makes it hard not to pity him.
- Although a lot of the villains in Arby 'n' the Chief are usually downright over-the-top like Craig, or downright hateful like Adam, the series's final villain, Eugene Black is certainly an interesting case of this. As evident throughout the show's final season, he's a downright sadist who has no trouble letting his psychopathic or pedophile friends do as they wish to people online, as well as enjoys forcing hundreds of innocent people to replace their Xbox 360s after banning them with a hardware corrupting software over a period of 2 months, just for laughs. On the flipside though, he's also a failing student at his school (despite also being a bully too), is constantly abused by his Drunk (and sometimes neglectful) Father, and his sister (the only source of happiness in his life) is dying a slow and agonizing death of Leukemia. It's hard whether to feel sorry for him for how crappy his life is, or to hate him for how much of a bastard he is just to repress these feelings. To add insult to injury, this only get worse for him, and he's Driven to Suicide by the show's end.
- Ask That Guy with the Glasses goes out with a strange mix of this and Death as Comedy. In the Grand Finale, someone asks him "do you have a question?". He gets so excited that someone finally thought about what he wanted that he literally explodes. Lampshaded by Chester A. Bum, who is sad when he first finds out about That Guy's death, but then realizes that he was a terrible person and it's probably a good thing he's gone.
- Llamas with Hats: It's oddly heartbreaking when Carl in the final episode gets Driven to Suicide by the realization that he's killed his former best (and probably only) friend along with everyone else on Earth.
- Critical Role has one with Delilah Briarwood. She and her husband Sylas are, by all accounts, a loving couple who care for one another very, very deeply. They are also truly terrible people, and are the ones responsible for the massacre of protagonist Percy's family and household and the trauma he endured as a result, as well as unknown other evils. But even after the horrible things they did, critters and players felt bad for Delilah, due to her absolutely heartbroken reaction when she saw Sylas killed right before her eyes.
- Marble Hornets: The two main antagonists of the series, Alex and Brian, both die with some degree of sympathy. Alex practically begs Tim to finish what he started, implying that while he may have gone Ax-Crazy, he nonetheless believed that what he was doing was right. Brian, on the other hand, is revealed to be the Hooded Man shortly after his own demise. Seeing the sharp contrast between his personalities before and after encountering the Operator makes the viewer sympathize with him as well.
- The Adventure Zone: Balance has a couple examples:
- At the end of The Suffering Game, Lydia dies of despair when Edward is killed; in her final moments, she drops her illusory form in favor of her true black robes, and, at a loss for words, simply screams.
- John might be the source and avatar of the Hunger, but watching him get subsumed by it is more than a little tragic. His actual death, watching the sunset with Merle before fading away, only makes him more sympathetic.
- Major Jakov. The sheer brutality with which Barry usurps and then murders him makes his death a dramatic moment, both for the audience and In-Universe.
- If he even counted as a villain, then Captain Murphy-he wasn't even a bad guy, just a harmless, if unstable, guy who went nuts and started making terrorist threats due to being trapped at the bottom of the ocean, but Archer's idiocy gets him killed, and he tells them how to escape the lab with his dying breath.
- In Beast Machines, Rhinox, a former ally, has become Tankor, a powerful enemy. After Tankor's death, the heroes hold a memorial for their fallen friend.
Cheetor: He wasn't just one of us... He was the best of us.
- Beetlejuice: Claire Brewster can be considered villainous, with her massive ego and strive to humiliate Lydia (she'd succeed if not for the Ghost With The Most). But one episode had her rung through the wringer on a Beetlejuice-staged foreign exchange student program to where she's dirty, dishelved and her clothes are torn. When she tries to enter her own home for a big fancy party, the butler dismisses her as a poverty-stricken waif. Lydia (at the party) sees Claire outside crying her eyes out, so she sneaks Claire in through a back window, cleans her up and gets her ready for the party.
- Vlad Masters in Danny Phantom, the Big Bad of the show, and performs his share of evil acts. Still, in his final moments he not only had to deal with the fact that everyone he wanted would not give him their love, but his most hated "friend" of all people rejected him when he refused to change his evil ways. Now, Vlad doesn't have anyone and is stuck in an area where he has to confront his greatest fear: loneliness.
- This happens a lot in the DC Animated Universe.
Batman (Terry): You gotta get out of here, Freeze! The whole place is gonna go!
- In nearly every Mr. Freeze appearance (except the one where he finally gets a happy ending and the one from The New Batman Adventures), he is defeated in a tragic and Tear Jerky way, culminating in this final exchange in his last appearance (both in Real Life and in the Universe timeline), where he lets himself be caught in a collapsing building.
Freeze: Believe me... you're the only one who cares.
- Solomon Grundy in a single episode (or rather two connected ones), goes from regular villain to sympathetic villain, who dies in his quest to attain his lost soul. For good measure, he's brought back again in a later episode, this time truly soulless, and has to be put down Old Yeller style.
- Similarly, Ace, the powerful psychic child who, in "Epilogue", has graduated to a full-blown Reality Warper, at the cost of her mind being on the brink of an aneurysm due to her psychic abilities. Batman sits beside her as she sets everything back to normal before the aneurysm kills her.
- General Shiva in Exo Squad; imprisoned for not slaughtering the Australian Resistance to the last man, he is given a chance to "redeem himself" by retaking Venus, which he knows to be a suicide mission. But, being a good soldier, he gives it a go anyways. When he gets shot down, even the Exoscouts who find him see it as a tragedy.
- Played for laughs in the Futurama episode "Anthology of Interest I". In a fantasy sequence, Bender is depicted as a giant who smashes up a city before being killed. As he lays dying, he laments he was unable to carry out his dream of killing all humans and expires on this line:
Bender: "Who's the real seven billion ton robot monster here? Not I. Not... I."
- Gargoyles has the Captain of the Wyvern Castle guard, who was so wracked with guilt for accidentally causing most of the Gargoyles' deaths when he betrayed Wyvern Castle to the Vikings that he spent the next thousand years haunting the castle's remains after his death.note Hakon was also haunting the site, but out of continued hate for Goliath (who ironically had nothing to do with either of their deaths who killed each other Disney style, although he wanted to deliver a gruesome kill). When Goliath shows up at the castle again, they harass him, make him hallucinate and attack his own friends, and, finally, drive him to an ancient ritual site where they can exchange his life for theirs. The Captain realizes what evil he is about to commit, repents, and uses his brief physical form to destroy the site. With his last moments, he thanks Goliath for forcing him to acknowledge his sins and begs for forgiveness as he travels to the afterlife. Goliath happily mourns him as a friend who is finally at peace. Hakon is still stuck, trapped within the ruined site, alone to wallow in his hate.
- In The Legend of Korra, Tarrlok and Amon/Noatak end up on a boat escaping Republic City after Noatak's lies are revealed to the public. Deciding they could not live, for any various amounts of implied, but unsaid reasons (being the legacy of an evil bloodbending criminal, knowing they'll be hunted for the rest of their lives, coming to terms with evil deeds), Tarrlok uses an Equalist shock glove to blow up the boat's engine, killing both of them. This follows Noatak having said he wanted to start a new life with his brother. Tarrlok even remarks "it will be just like the good old days," and Noatak remarks how he almost forgot the sound of his own name and sheds shed a single tear right before the explosion. Depending on who you ask, the tear indicates (among other interpretations) that he knew what Tarrlok was about to do and didn't try to stop him, or that he genuinely wanted to have the peaceful life with his brother that he'd been talking about.
- Book 3 gives us...every member of the Red Lotus inner circle except Zaheer. Even if someone's that much of a deadly ruthless bastard, being stuck in a Tailor-Made Prison (two of which were hellish) for thirteen years is bad enough without ending up obliterating oneself via the pyrokinetic equivalent of a shaped charge, being electrocuted, or dropping a cavern on oneself to avoid ending up back in the aforementioned cell. (Add to that the fact that these characters were a former child soldier, a tiny and visibly disabled woman who spent her time in prison imagining what made her jailers tick, and one of the most blatant antivillains to ever appear in a kids' cartoon.)
- Samurai Jack:
- It's very hard not to feel sorry for the Villain Protagonist of the "The Tale of X9" episode , a robotic assassin, who was one of several murderous robots created by Aku, but was the only one given emotions and feelings. After years in the service of Aku all the other robots of his series have been destroyed, but he has survived because of his emotions. However, when he meets a tiny dog named Lulu (sweet thing), he finally hangs up his assassin hat for good. Unfortunately, when Jack arrives, Aku becomes desperate and decides that he has to pull his greatest assassin out of retirement by holding Lulu hostage. Jack knows nothing of this, and when X9 launches his attack, Jack cuts him down just as effortlessly as he would any other mook. His final words are asking Jack to finish caring for his now abandoned charge.
- Princess Mira from "The Princess and the Bounty Hunters" is another enemy of Jack's that is after him for a noble cause; she hopes to use him as a bargaining chip to free her nation from Aku's tyranny. When she and her allies ambush Jack, he effortlessly dispatches all of them with only Mira standing. Realizing that she is so badly outclassed by the samurai, Mira can only slump over and cry, seemingly accepting that she will never save her people, while Jack wanders off into the forest without a word.
- In Season 5, Jack is pursued by female assassins known as the Daughters of Aku, whom were brutally trained from birth by their abusive mother with the purpose of killing the samurai. While Jack himself is initially unaware of this, its made abundantly clear to the viewer that they were just abused young women than anything else. When he is forced to kill one in self-defense, its treated as a very somber moment for marking the first time he killed a real human being and not a robot. And after killing five more in combat, Jack is so wracked with guilt he begins to hallucinate with dozens of crows calling him "MURDERER".
- The death of Spider-Carnage in Spider-Man: The Animated Series. He was a demented, Ax-Crazy loon who was trying to set of an Omniversal Metaphysical Annihilationapocalypse, but when he has a Heel Realisation and kills himself it's all but impossible not to feel bad. There's just something about seeing someone with the face of the show's hero brought so low that not only does suicide seem like a good idea, it's the best option that there is.
- Savage Opress from Star Wars: The Clone Wars caused more than his share of death and destruction while apprenticed to Count Dooku, Asajj Ventress, and later Darth Maul. However, this was due in large part to his brainwashing at the hands of the Nightsisters, and when he is unceremoniously impaled on the lightsabers of Darth Sidious, he dies in his brother Maul's arms, expressing regret that he had not reached Maul's expectations.
- In Star Wars Rebels, the death of Darth Maul is a major Tear Jerker, one of the biggest in the whole series, when he realizes how badly he's failed and how much of his life has been completely wasted. He's past his prime, everything he has worked for is for nothing, his family is dead, and he spends his time tracking down Obi-Wan Kenobi for one more duel. As Maul dies, the two have a quiet conversation on the Chosen One and Maul saying that he will avenge "us" - Maul, and either his brother or Obi-Wan.
- Also from Rebels, there's Imperial Lieutenant Yogar Lyste. Despite being a jerkass who seized land from innocent farmers for the Empire, it's hard not to feel sorry for him when he gets framed for treason by the actual Reverse Mole. He's last seen being dragged away protesting his innocence, and the only person who actually seems to care about what happens to him is the same man who framed him in the first place.
- Jasper from Steven Universe. Before being corrupted, she's revealed to be an angry and vengeful loyal soldier who, from her point of view, lost her colony, her planet and her leader (Pink Diamond) because of Rose Quartz. She spends her last moments roaring at Steven for every wrong she thinks Rose Quartz did. On top of this, it's implied she's nothing more than the equivalent of a grown up Child Soldier who's been indoctrinated from birth to think the way she does. Word of God later confirmed that she refused Steven's help because she hated herself for being (in her eyes) too weak.
Bismuth: You should have shattered me back then. At least if I were in pieces, I wouldn't have to know how little I mattered to you! You didn't even tell 'em. You bubbled me away and didn't ever tell your friends. My friends!
- Bismuth is also this. Fighting in the war against Homeworld, she saw her comrades shattered at the hands of Homeworld Gems. She believed they'd lose the war unless they stopped following Rose Quartz's policy of not shattering enemy Gems. When she made a weapon designed to do just that, Rose was mortified. She poofed Bismuth to keep her from telling the others, and lied to her friends about her disappearance for 5000 years. When Bismuth is stabbed with Rose's sword by Steven, she delivers some heart-wrenching words before she poofs.
Steven: I'm going to tell them. I'm going to tell them everything.
Bismuth: *chuckles* Then you really are better than her.
- The Rubies are a generally incompetent, childlike morons, aside from Eyeball, who has a little more experience due to being a Shell-Shocked Veteran. All of them are Thrown Out the Airlock by Steven, a possible Fate Worse than Death, due to the fact Gems don't need to breathe and are The Needless, condemning them to a possible eternity of floating through space, something Steven expresses heavy guilt over in later episodes, in addition to the fates of Jasper and Bismuth.
- In the Teenage Mutant Ninja Turtles (2003) episode Nano, a colony of Nano Machines are separated from the main group, and create a body made from junk, which is found by a jewel thief who "adopts" it (seeing as it has the intelligence and personality of a child) and uses it to commit crimes. Eventually, as the nano-bots multiply and it gets stronger, the Turtles have to destroy it by dumping it in a vat of molten iron, but they're pretty bummed about it later:
Michelangelo: I kinda feel sorry for the guy. He was like a little kid.Donatello: Too bad he had such a rotten father...
Leonardo: You heard the man. Let's go stop the Shredder.
- Hun in Turtles Forever, after the Turtles finally convince him that The Shredder is going to destroy The Multiverse. Hun is erased from reality right afterwards. The same thing happened to Casey and April; they both get better once reality is restored, Hun was likely brought back too.
- Transformers Prime.
- The Decepticons got some of their members killed unceremoniously. Breakdown was eviscerated by Airachnid. And Dreadwing, who wanted to kill Starscream who zombified his brother Skyquake, was killed by Megatron for disobeying his order to stand down.
- Additionally, several MECH members end up being killed by Silas as he views them as useless now he is a human-Transformer hybrid, just after they saved him of all things. It's pretty hard not to feel sorry for them in this case.
- TRON: Uprising: Keller's a scientist forcibly drafted into the occupation to force them to mind control other programs. She chafes, and helps the Renegade stop her concoction before going on the run, with the Occupation force chasing after her. She spends an entire episode in a state of panic, trying all manner of options to desperately escape while trapped on a train, nearly dying at least twice, and Beck, sympathetic to her position, trying to recruit her. At the very end, cornered, she goes back to the Occupation with Paige promising her no harm, but not before covering for Beck so no one knows he's a Resistance sympathizer. She goes to back to the general, who welcomes her back, and kills her like every other minion who displeases him.
- Wakfu, at the end of the series. Poor Nox.
Nox: Twenty minutes? All that wakfu spent for a jump of twenty minutes in time? Two hundred years of researching and collecting wakfu for twenty miserable minutes?! NOOOOOO!
- The real kicker is when Yugo chews Nox out for committing so many atrocities in the name of his delusions. Finally seeming to understand the truth, or that he never had a chance of seeing his family again, Nox breaks down crying. When the soldiers of Sadida show up to pass judgement on him, he doesn't put up a fight.
- Likely because, on top of everything else, Nox had managed to convince himself (and attempted to convince others) that it was okay to do any horrible thing in pursuit of his goals because it would all be undone when he finally succeeded. He'd get what he wanted and no one would really be hurt. But of course, it didn't work out that way.
- Actually, he doesn't die then. Instead, he teleports away and travels to the grave of his beloved family, whom he wanted to see again so badly that it was the key motivation for everything he'd done, and dies either by quietly killing himself or running out of power after he surrendered the Eliacube to Yugo and couldn't draw on its energy anymore. Take your pick on which is even more depressing.
- The real kicker is when Yugo chews Nox out for committing so many atrocities in the name of his delusions. Finally seeming to understand the truth, or that he never had a chance of seeing his family again, Nox breaks down crying. When the soldiers of Sadida show up to pass judgement on him, he doesn't put up a fight.