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Pyrrhic Villainy

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Agent Valentine: You have broken every arms embargo written. There is enough evidence here to put you away for consecutive life sentences. I don't think you appreciate the seriousness of your situation.
Yuri Orlov: My family has disowned me. My wife and son have left me. My brother's dead. Trust me, I fully appreciate the seriousness of my situation. But I promise I won't spend a single second in court.
Agent Valentine: [after Yuri is proven right (on both counts)] I would tell you to go to Hell, but I think you're already there.
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The villain always loses, right? Actually... no. Sometimes the villain surprises us all and is victorious, even if only in the short-term. However, victory comes with a price. Both they and the audience may well ask if it was worth it. Often this takes one of two forms: either it has taken so much effort (and such underhanded methods) to win that it has left the good guys as the moral victors with a better legacy, or in order to accomplish their goal the villain has had to sacrifice what they cared for most and/or made them likable and/or relatable-to for the audience.

So while their efforts might have paid off, to answer the earlier question of whether it was worth it: frequently it is not.

See also The Bad Guy Wins, for where the villain doesn't suffer from this (though he or she may still incur some cost). This sort of plot may be found in a villain's Start of Darkness, back when the villain was either a hero or a much lesser villain, and first turned to true villainy, bringing victory... but at a cost. On the other hand, really top notch villains may win without sacrificing everything, only to find that Victory Is Boring. A Meaningless Villain Victory is when the villain wins but a sudden unforeseen event renders their victory hollow and their efforts for naught. Being Evil Sucks also counts if the villain in question has a Heel Realization about the choices he made.

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This is an Ending Trope, so beware of unmarked spoilers!


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    Audio Play 
  • In Kankinkon, the most powerful man in the setting, the Saijou family patriarch Touji, has accomplished this. He used his connections, riches, and good public face to kidnap the woman he fell in love with, force her into marriage, and then fool her family into thinking she was taken care of after hitting her head and giving him their blessing. He even received a son and heir out of the ordeal, had his family curse put to an end though the boy, and gets to have wild sex with her whenever he wants, but none of it even matters since he grew to only desire her love. And he will never get it, because he trapped her into the marriage in the first place.

    Comic Books 
  • Doctor Doom:
    • In Emperor Doom, Doom succeeds in conquering the world by brainwashing everyone. By and large, he's a fairly benevolent monarch and does much to solve many of the world's problems. Unfortunately, he's so bored out of his mind that when the one unaffected hero manages to break the spell on a few others, he lets the rebellion win. He'd rather be a conqueror than a Desk Jockey.
    • This is a running theme with Dr. Doom; every time he manages to take control of a nation/planet, he'll spruce the place up very nicely and run it better than most governments ever manage, but will ultimately get bored of running it. Doom enjoys the challenge of taking over a nation and solving problems, not the mundane managerial work of keeping national status quo. The exception is in Doom 2099. He conquers the United States, and actually intends to keep power, so he can fix the entire world. It doesn't end well for him, the country, or most of the heroes.
    • In Triumph and Torment, this is how Doom saves his mother.
  • The end of the Civil War plays with this: Iron Man's reputation has essentially become mud because of his support of the SHRA, and it's only further compounded by Captain America's death.
    "It was the right thing to do! And I was willing to get in bed with people we despised to get this done. And I knew the world favors the underdog and I would be the bad guy."
  • Sonic the Hedgehog (Archie Comics) had an early, non-canon Yet Another Christmas Carol where Robotnik is taken to see the future. Robotnik has finally defeated the Freedom Fighters, but he has rendered himself the last man alive in doing so, turning Mobius into a barren wasteland. However, Robotnik doesn't grasp this and fails to learn his lesson.
  • Blacksad: Faust LaChapelle from "A Silent Hell" will never be punished for his crimes while he was a Snake Oil Salesman, as everybody who could expose him is either dead or a nobody without a voice. However, Faust's guilt is also consuming him, he has alienated his own son, and is dying of cancer anyway.
  • In Marvel's "What if Juggernaut killed the X-men", the Juggernaut successfully kills Xavier and the X-men, but he doesn't get to enjoy it because without the X-men to stop them, the Sentinels release a poison gas into the atmosphere that kills everyone but Juggernaut due to his powers, and he finds that he can't interact with people hiding in shelters because breaking in exposes them to the gas. So he's all alone in the world, forever.
  • The Boys ends with Vought still up and running under a new name, but at the cost of their main source of income, superheroes, being out of the picture after most of them were killed in their coup attempt against the U.S. government, Butcher leaking everything they had on them to ruin the ones that weren't, and Hughie threatening to go through with Butcher's Final Solution should they ever overstep their bounds again. Stillwell, who spent the entire course of the series being an unfeeling sociopath willing to do anything to improve Vought's bottom line, has a Villainous Breakdown after realizing his years of scheming led to nothing.
  • While not technically a villain, the Finance Smurf from The Smurfs comic book story of the same name gains the entire village after all his fellow Smurfs, including Papa Smurf, have left it behind along with all their money...only for himself to be left without anybody to share his new-found good fortune with, making him very sad and lonely. This makes Finance Smurf come to his senses and go out to find the Smurfs to tell them he's giving them back everything and abolishing the money system.
  • Played with in The Batman Adventures's final issue with "Fear Itself": Joe Chill ended up in jail on an unrelated charge after shooting Thomas and Martha Wayne, meaning that the policenote  overlooked him. By the time he finds out just who he shot — and just who the boy that he'd spared that night was — said boy's become an "untouchable millionaire" long out of Chill's reach, and Chill is depicted as seeming to be living relatively scot-freenote ... except for his constantly hallucinating the adult Bruce Wayne's face wherever he goes, spending every day day in mortal fear that someday Bruce Wayne will remember his face and finally finger him to the cops. Not only do Batman and a GCPD detective both not recognize his face, Batman actually mistakenly believing Chill to be a henchman of Killer Croc'snote , but finding out his real name and his alias doesn't ring a bell either, meaning that Joe Chill was in a hell entirely of his own making.
  • At the end of the "Kindly Ones" arc of The Sandman, Lyta Hall, aided by the Kindly Ones, succeeds in killing Dream and avenging her son's apparent death. There's just one problem: Daniel wasn't actually dead, and for her crimes against the Dreaming, he is forced to become the new Dream, so she will never, ever get him back. And on top of that, her actions have pissed off a lot of people, leaving her with a lot of enemies.
  • In Injustice 2 (the comic book prequel to the video game of the same name), Ra's al Ghul manages to get rid of the corporate executives polluting the world as well as successfully assassinating the President of the United States for his anti-environmental policies with none of the heroes being able to stop him. However, in the process his animal reserve with several endangered species being devotedly guarded by Ra's gets destroyed during a battle with the superheroes, leading to their species being practically extinguished. He lets his enemies go because there is no more point in fighting, and makes sure to tell them whatever victory he made that day is meaningless due to the price paid before swearing to carry on the fight even more ferociously.
  • Avengers Undercover: Arcade laments his situation in #3. He can't outdo what in did in Avengers Arena, not to mention he's hunted by superheroes outside of Bagalia. #10 reveals he fully demanded respect he thought he earned with Murder World, only Zemo and the others chose to reward Corriander for putting the setting together in the first place.
  • Empire: Golgoth wins, but it's heavily implied to be a hollow victory since he's lost everything that's important to him in the process, and it's highly unlikely that his empire will survive him.
  • In Superman storyline Last Daughter of Krypton, Supergirl defeated Simon Tycho's private army, beat him up, got her stolen Sunstone back and blew his space base up. As for Simon Tycho himself, he lost the lower half of his body because of the explosion. Still, because he got a sample of Supergirl's blood completely by accident, he thinks he came out on top.
  • Watchmen ends with the Big Bad Ozymandias successfully carrying out his Evil Plan to kill millions of people as part of a Genghis Gambit to prevent World War III. However, he makes it painfully clear that he never wanted to hurt anyone, being Necessarily Evil, and looks to Dr. Manhattan for reassurance that it was all worth it. Manhattan implies that world peace ultimately won't last (leading Ozymandias to a subtle Villainous Breakdown), with the final panel of the comic showing that Rorshach had delivered his journal detailing the plan to a local paper as a Dead Man's Switch. In fact, Ozymandias' entire character is a subtle Whole Plot Reference to the Percy Bysshe Shelley poem of the same name about how all of Ramses II's achievements were ultimately forgotten by time.
    • In the sequel Doomsday Clock, it's shown that his efforts truly were All for Nothing as the public figures out he's a fraud within a decade and the peace he built comes crashing down as an international manhunt for his head starts, leading Ozymandias to search for Dr. Manhattan seeking help cleaning up the mess he caused.

    Comic Strips 
  • A minor example in Retail occurred when Josh, the assistant manager for Grumbel's, lied about getting a job offer from a competing store in order to secure a raise. He initially got away with it...until Marla (the store manager) found out about it, and proceeded to tell Stuart, their district manager who was formerly Josh's supporter. No longer having Stuart's protection, and with Marla planning to fire him, Josh quickly got himself a new job and quit.
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    Films — Animated 
  • Tad, the Lost Explorer: A band of mercenaries called Odysseus led by the intimidating Kopponen seek the Idol of Paititi to gain immortality. However, seemingly acclaimed archeologist Max Mordon also turns out to be a mercenary seeking the same relic and is Kopponen's boss. Mordon actually succeeds in obtaining the idol...but turns out the idol only grants immortality to those who hold it by turning them into mummies! Thus, he is transformed into a living mummy and sent to the Mummy prison for all eternity.

    Films — Live-Action 
  • Michael Corleone might be the ultimate example of this by the end of The Godfather movies.
    • Part 1: Certainly he's destroyed every major underworld power in his way but at the cost of his soul.
    • Part 2: Again he destroys his enemies and takes on the US government and wins, but he's also destroyed his marriage, alienated his children and friends, killed his brother, and is left utterly alone.
    • Part 3: He passes leadership of the family but fails to legitimize it, his daughter is killed right in front of him and finally he dies alone and unhappy.
  • Daniel Plainview's empty isolation and drunken insanity at the close of There Will Be Blood. And his now immortal final line: "I'm finished!" implies that the way his life turned out is exactly what he wanted.
  • The movie version of The Talented Mr. Ripley has Ripley having to kill everyone he likes in order to get away with it. The book ends by indicating that he'll never be able to look at another policeman without that flash of alarm that says "This is it — he's the one — he knows." Not a way anyone would like to live life.
  • Star Wars:
    • Kylo Ren in The Force Awakens. Obsessed with setting himself in the image of Darth Vader, his personal hero and grandfather, he has eradicated the new Jedi Order started by Luke Skywalker and joined the First Order in restoring the shattered Galactic Empire, but he has grown so emotionally and mentally unstable that his First Order allies can't completely trust him, and in the end, he has by murdered his own father, Han Solo at the behest of Snoke in an (failed) attempt to eradicate the Light within himself. It's hard not to pity him.
    • The First Order by the end of the The Last Jedi. By all but wiping out the Resistance, they've become the only major superpower in the galaxy, but their Supreme Leader Snoke is killed, their fleet was devastated, and they experienced immense casualties just to take down a relative handful of ships and rebels. In the end, their new leader Kylo Ren humiliated himself in front of his army, highlighting his inexperience and rashness for all to see, and his actions allowed a number of Resistance members to escape from them as a result, preventing a complete victory for the First Order. The only reason they managed to gain any victory at all despite their incredible losses to the amount gained is that their surviving forces still vastly outnumber and outgun the remaining Resistance at the end, making it a win by technicality. Which didn't matter as within a year, the Resistance manages to build back its former strength, and the First Order lost so much of its original fleet that they're forced to ally themselves with the resurrected Palpatine's Final Order, which motivates the entire galaxy to strike back at the First Order as one unified, overwhelming force.
  • By the end of 300, Xerxes has lost most of his best troops and although he's defeated Leonidas at Thermopylae, the performance of the Spartans and the losses inflicted among his men has only given new determination and inspiration to the other Greeks. Historically speaking this was only a minor setback for the Persians, but other Greeks counterattacked and forced the Persians to leave the country; therefore Xerxes won the battle but lost the war because the choke point of Thermopylae bought the other Greeks enough time to mass for their counterattack.
  • By the end of Pat Garrett and Billy the Kid, it's clear that Garrett realizes that he will lead a conflicted, unhappy life and will be chiefly remembered for killing his friend. Billy, meanwhile, will have most of his bits of sociopathy forgotten by an adoring public (to an extent, this extends to other portrayals of the two, including Young Guns II).
  • In House of Flying Daggers, The Mole for La Résistance accomplishes his mission to perfection, but loses the Action Girl he loves, and later kills her while fighting The Rival who had won her love. He ends the film a broken shell of a man.
  • In Lord of War, Villain Protagonist and Arms Dealer Yuri Orlov manages to evade the law and escape a long stay in prison to continue his gunrunning. However, this comes at the cost of his brother and uncle being killed, his parents disowning him, and his one true love divorcing him and taking his only son with her. He was also released only due to being useful to the U.S. Government and he's fully aware they can have him disposed of if his usefulness ceases.note  This is hammered home when the Interpol agent chasing Yuri says that normally he'd tell Yuri to go to Hell, but he thinks that Yuri's already there.
  • In the Hong Kong action crime drama Sha Po Lang (or Kill Zone in the U.S.), Triad crimelord Wong Po, the villain played by Sammo Hung, defeats the hero Inspector Ma played by Donnie Yen by sending him right out a window... right onto the Wong family's waiting car with Po's beloved child and wife still inside, killing all three of them.
  • Star Trek II: The Wrath of Khan: Khan's ruthless, vicious bid to exact revenge on Captain Kirk succeeds (up to a point), and he even acquires what might be the most powerful piece of technology in the 23rd century. Unfortunately, this success led to him sinking deeper into insanity, leading his devoted followers to their deaths, getting disfigured, and finally committing suicide in an effort to finish off the object of his fixation. Early on, his own right-hand man pointed out that he had already achieved a limited victory and could fly away without suffering any consequences. Naturally, his advice went unheeded.
  • Real Steel has Zeus declared the winner of the match between him and Atom despite the latter knocking the former out, keeping his status as the unbeatable champion. However, Zeus is booed by the crowd who embraces Atom as the "people's champion."
  • Marvel Cinematic Universe:
    • In The Avengers, Tony tries to explain to Loki that this is the best he can hope for.
      Tony Stark: You're missing the point, there's no throne. There is no version of this where you come out on top. Maybe your army comes, and maybe it's too much for us, but it's all on you. Because if we can't protect the Earth, you can be damn sure we'll avenge it.
    • In Avengers: Infinity War, Thanos succeeds in his mission to kill half the population of the universe, but his armies and followers are wiped out, and he chooses to murder the person he loves the most to achieve his goal.
      What did it cost?
      ...Everything.
    • And by Avengers: Endgame, he's lost even more. The Avengers track him down and kill him, and his plan was All for Nothing because the Avengers bring them all back by using time-travel to re-create the Infinity Gauntlet. It's no wonder his past self just loses what little composure he originally had when he finds this out and resolves to destroy the world and remake it in his own image.
    • In Spider-Man: Far From Home, Mysterio succeeds in being known as a great hero, one he engineered for himself via a Monster Protection Racket that took many lives. He even defames Spider-Man by revealing his Secret Identity to the world, and tarnishes Tony Stark's legacy in the process. The catch is that all of this could only be done posthumously, as he died in the final battle when his own arrogance got him shot in the crossfire between Spider-Man and his drones.
  • In The Hunger Games: Mockingjay Part 1, Katniss warns Snow about this, stating "if we burn, you burn with us." Snow even acknowledges the fact that the Capitol needs the Districts to survive. That said, if it's a choice between capitulation and domination, Snow proves more than willing to slaughter as many people as it takes to stay in power.
  • The title character in Nixon manages to become President using lies, dirty tricks and backroom deals with big business and government officials... yet can't enjoy his Presidency, because he's too busy trying to destroy his enemies. Arguably Truth in Television: after his 1972 election, where Nixon won 49 of 50 states, Nixon complained that he didn't win enough votes and immediately fired half of his staff.
  • Gillo Pontecorvo's Burn!, set on a fictional Portuguese colony in the Caribbean. The protagonist, English adventurer William Walker, incites a slave uprising to secure the island for British sugar interests. When the slaves continue fighting against the British-backed government, Walker returns with British troops to crush them... destroying most of the island's sugar crop in the process. Walker eventually succeeds, but destroys the island's cash crop and is killed himself.
  • Batman v Superman: Dawn of Justice: On paper, Lex Luthor succeeds in getting Superman killed thanks to Doomsday. However, he ends up in jail as a result, Batman is keeping an eye on him and will work with Wonder Woman on starting the Justice League, Superman is now remembered by everyone as a hero and will come back.
  • C.S.A.: The Confederate States of America: By the early 21st century, the CSA has maintained chattel slavery of Africans, revived the international slave trade, and shows no sign of slowing down. However, every other major country (except South Africa) maintains sanctions against it, and its oppressive "morality" laws and Culture Police have driven cultural icons into exile in Canada, with its only art being government propaganda. At the end of the film, it is stated that the stubborn adherence to slavery is weakening the country's economy, and it will eventually fall.
  • Kingsman: The Secret Service: Valentine sought to save the world by eliminating pretty much its entire population using a Hate Plague to kill each other, save for a few individuals that willingly sided with him. In a sense, he gets what he wants since people die during the ensuing chaos (though not all of them), but also the world leaders that denied climate change and only cared about staying in power. The problem is that all his collaborators were killed off by Merlin, and he gets killed by Eggsy at the end.
  • On its continuation Kingsman: The Golden Circle, Poppy Adams' plan to hold the millions of people that have ever taken drugs legally or not (or had been affected biologically by drugs, such as kids that had their parents taking drugs while they were in the womb) around the world hostage with her virus, in exchange for having all recreational drugs legalized in the U.S., hits a bit of a snag on its execution: The President of the United States turns out to be a Knight Templar and decides it would be better to let those millions die and declare himself the de facto winner of the War On Drugs. If not for the Kingsmen managing to Storm the Castle and get the antidote, the result would have been Adams going down in history as the architect of a world-wide genocide and the complete annihilation of her monetary base. For added irony, she dies without knowing this.
  • Saw: In the end, Jigsaw's actions result in the deaths of his own, his disciples who were qualified enough to succeed him, and his ex-wife. The only thing he leaves behind is his murderous legacy, which is the antithesis of everything he claimed it to be.
  • Catch Me If You Can: While Frank is able to continually evade the FBI and get rich off his cons, this comes at the cost of him being almost permanently estranged from his family and being unable to form close relationships with anyone for fear of them discovering his deceit. The psychological pressure of continuing a life of crime eventually causes him to crack and turn himself in.
  • The Night Flier: Dwight Renfield escapes in his airplane after slaughtering dozens of people, with all his crimes being pinned on Richard Dees. However, he did not want Dees to die in the process, and Dwight actually hates his own existence as a bloodsucking fiend.
  • Jingle Jangle: A Christmas Journey: Brings us Gustafson. He worked under Jeronicus Jangle, the greatest inventor of all time and even came up with an invention of his own that he begs Jeronicus to just look at for a moment due to the fact it never functioned properly. Jeronicus is dismissive and seems more preoccupied with spending Christmas with his family as well as working on a groundbreaking invention. After a little goading, Gustafson steals Jeronicus' book of inventions and uses it to become a famous toymaker leaving Jeronicus broken and destitute. Once out of stolen ideas, he returns to his one original invention only for it to fail miserably and prompt him to try stealing something else from Jeronicus. His efforts are thwarted but as he's being led away by the police, Jeronicus insists on giving him a gift: The part he needed for his invention to work. The nail is further driven in when its revealed that Jeronicus planned to surprise Gustafson with it the night he left. Gustafson is left dumfounded and can only manage a long last look before being taken to jail.
  • The Wicker Man (1973): Lord Summerisle and the villagers succeed in burning Sgt. Neil Howie alive - but the latter predicts that should the crops fail next year, the former will be betrayed and murdered by his own cult. His grimace upon hearing it heavily suggests that he knows that if Howie is not accepted, then his days are numbered.

    Literature 
  • Patrick Bateman from American Psycho gets away with everything, but is just as miserable and lonely as he was in the beginning. Nobody actually cares about him, and there are implications that all of his crimes only happened in his own sick mind anyway.
  • The Four Gospels' Judas Iscariot may be an example. Sure, he got a tidy sum for betraying Jesus, but, according to Matthew, he was so overcome with guilt afterwards that he hanged himself.
    • Exactly how things worked out for Judas varies a bit depending on who's telling it. The Gnostic Gospel of Judas (rejected when New Testament's contents were formalized) even claimed that Judas "betrayed" Jesus under Jesus's orders.
    • Jesus said, "Truly, I say to you, one of you will betray me, one who is eating with me... For the Son of Man goes as it is written of him, but woe to that man by whom the Son of Man is betrayed! It would have been better for that man if he had not been born." (Mark 14:17 & 21, ESV)
    • And of course, that "tidy sum" of earthly treasure is a mere pittance compared to the honor his fellow apostles would have of "sitting on twelve thrones, judging the twelve tribes of Israel", not to mention sharing in the same inheritance that the Lord and His believers would receive from His Father. To compare it to another part of the Bible, Judas' thirty pieces of silver is the equivalent of Esau's bowl of pottage which he traded his birthright inheritance for with his brother Jacob, which brings us the Aesop that sacrificing one's future (heavenly) inheritance in exchange for the satisfaction of immediate short-term (worldly) gain isn't a good thing.
  • In the book of 2nd Maccabees, Jason the corrupt (and eventually former) high priest continued to slaughter Jews in chapter 5, without realizing that a victory that destroys his own people is the worst possible defeat, because he was thinking he had won a battle against enemies rather than against other Jews.
  • In Test of the Twins, Raistlin Majere's goal of becoming a god is revealed to be a severe case of Pyrrhic Villainy. He succeeds, but in the process he destroys the world and eradicates every shred of good in his own soul, leaving him with no ability to renew or heal that which he has laid waste. Fortunately for all concerned, his brother Caramon is able to go back in time and reveal this outcome to the earlier Raistlin, who then sacrifices himself to save Caramon and Crysania.
    • He thinks of it differently, as revealed during his nephew's test to become a full-fledged mage.
      Raistlin: I sacrificed myself to save myself.
  • In the William Gibson short story "Dogfight", the main character wins the aerial combat video game, but in the process alienates everyone he might possibly celebrate his victory with.
  • Sure, by the end of PLAGUE (4th GONE book), Caine Soren finally got that important position of evil dictator he was pushing for since book 1, but at what cost? Oh yes, A) He doesn't really have supreme control at all. B) Everyone hates and disrespects him. and C) the love of his life just left him for his twin brother/arch enemy. And she's pregnant with his demon child, who certainly stirs shit up for him later. Some victory that turned out to be.
  • Several instances occur within A Song of Ice and Fire:
    • Cersei makes her illegitimate son Joffrey king but was unable to stop Ned Stark from informing Stannis Baratheon that he is the true king or stop Renly from leaving the city and proclaiming himself king. Joffrey then executes Ned causing the North to declare independence and they capture Jaime. The Lannisters gained the throne and a three front war to match.
    • Tywin Lannister destroys the Starks as a noble house. In the process, his eldest son is crippled by Tywin's own mercenaries and later denounces him, Gregor Clegane renews tensions with Dorne and his last-minute Tyrell allies poison his grandson and take a large chunk of his political power.
    • The Freys gain possession of Riverrun and a number of other perks for perpetrating the Red Wedding. They're currently the most despised house in Westeros and are being killed one-by-one by the Brotherhood Without Banners and Wyman Manderley.
    • Roose Bolton becomes one of the most powerful men in Westeros for betraying and murdering Robb Stark. He also inherits Robb's war with the Greyjoys, a war with Stannis, the imminent invasion of the Others, and only a handful of Roose's new vassals aren't actively plotting against him. His only heir is his sadistic bastard son Ramsay Snow, whose endless parade of Stupid Evil actions are rapidly destroying what little support the Boltons have left. When he marries Ramsay to "Arya Stark" (actually Jeyne Poole) to secure their hold on Winterfell and the North, Ramsay abuses and rapes his new young wife for his own sadistic pleasure, so it's no surprise that she takes the first opportunity to escape the castle.
    • Archmaester Gyldayn's Histories chronicled Aegon II's successful usurpation of the Iron Throne but by the end, he is deformed, his dragon and his family are dead, his forces are depleted and he has no heir save his nephew who is the son of his nemesis. Still, he remained defiant against the rebels. He is poisoned to end the war.
  • To Kill a Mockingbird: Bob Ewell is able to get away with severely beating his daughter and having a black man framed for it and imprisoned. But anyone watching the trial knew what he did, destroying what remained of his reputation, and driving him to harass the wife of the black man he imprisoned, spit in Atticus' face, invade the home of a judge, and later attempt to murder Jem and Scout, an action that got himself killed by Boo Radley.
  • And Then There Were None:
    • Vera's lover Hugo refused to marry her because he wasn't financially well-off enough to support her, so she decided to solve that problem by letting his nephew Cyril drown at sea so that Hugo would get the family inheritance instead of him. However, Hugo can tell that Vera wasn't honest about her claims that Cyril's death was just an accident and since he genuinely loved his nephew, he leaves her, meaning that her horrifyingly extreme attempt to get the man she loved to marry her only ended up driving him away from her for good.
    • General Macarthur, after learning that his wife was cheating on him with one of his officers, sent that officer on a virtual suicide mission to get rid of him. It worked, but his wife died of a broken heart soon after, leaving Macarthur alone and utterly consumed with grief and regret for the rest of his life. By the time U.N. Owen starts offing people on the island, he's ready to accept death as the fate he deserves.
  • Five Little Pigs: The murderer of Amyas Crale has long since gotten away with the crime, with Amyas's wife Caroline taking the fall (and having since died in prison). Even when Poirot confronts the person at the end, he admits that he can't actually get them convicted. Elsa may have escaped legal consequences, but all she accomplished was killing the one man she ever really loved, and she was deprived of even the satisfaction of hurting Caroline by Caroline's dignity in the face of imprisonment. While she's now wealthy and above investigation, she lives an empty and miserable life, and considers herself more dead than her victims.
    She and Amyas both escaped — they went somewhere where I couldn’t get at them. But they didn’t die. I died.
  • Gone Girl: On paper, The Bad Guy Wins; Amy literally gets away with murder, and gets everything she wanted in the end. But she still isn't happy. She's still an empty, miserable person with nothing to live for except maintaining the façade of a perfect life and marriage. The husband she's essentially made her prisoner even admits he just feels sorry for her, which enrages her.

    Mythology & Religion 

    Music 
  • In The Willow Maid a man wants to force the titular willow maid to marry him. He succeeds in chopping down her tree and dragging her out of the forest ... but once she is out of the forest, she turns into a flower. Thus, his plan to make her bear his children will likely not work out.
  • Metallica's "King Nothing" is about a person who uses extreme methods to achieve a goal, stopping at nothing to get it and letting nothing stand in their way. They get it, but everything comes crumbling down and they're left with nothing. They sacrificed everything for something that was worthless in the end.

    Tabletop Games 
  • Werewolf: The Apocalypse's final book, Apocalypse, features one scenario in which the Weaver takes centre stage as the main villain of the setting instead of the Wyrm, and can actually end with the Weaver eliminating all threats to her perfect world by sealing the Gauntlet shut, separating the physical world and the spirit world once and for all. Unfortunately, this means that the spirit world is sentenced to entropic breakdown without a physical world to reflect, and the real world loses its vital spark of creativity without the spirit world to provide it; not only do humans lose their ability to dream and innovate, but all life in the universe begins a steady decline into extinction. For all intents and purposes, the Weaver's chance to create a static utopia has been lost forever, and thanks to the separation of the two worlds, there's nothing she can do to stop it.
  • Mage: The Ascension: The Technocracy is winning the war against the Traditions and moulding Consensus in favour of its vision of reality, only to discover too late that the stamping out of the spark of creativity, freedom and independence it had done in the process has also resulted in the Masses deeming its own superscience too fantastic to be plausible. In this setting, how openly one can use magic is affected by how easily it can be passed off as something nonmagical, lest you incur Paradox, and given that the Technocracy is really doing Magic Powered Pseudo Science despite its self-delusion and indoctrination to the contrary, this is quite the problem.
  • Warhammer 40,000:
    • The reason Tzeentch (god of hope, backstabbing, mutation, and magic)'s plans always end up failing at some point is because if he did achieve ultimate and final victory over everyone else, he'd have nothing left to hope for, and no purpose to his existence. Thus his plans always require the failure of a previous one and are intended to be overturned at some point.
    • Subverted with the orks: in the event that they actually manage to kill off all other species in the galaxy (which they came dangerously close to doing once), leaving them no one else to fight... they'll happily turn on each other.

    Theatre 
  • The ending of Sophocles's Antigone, in which the sympathetic Anti-Villain Creon succeeds in bringing his rebellious niece to justice, but at the cost of his entire family, makes this Older Than Feudalism.
  • The MacBeths killed King Duncan, forever destroying the mental peace of Lady Macbeth and turning Macbeth into a Fallen Hero who essentially sold his soul to the devil, all for a temporary victory. In the long term, what they accomplished was to make Banquo's descendants kings.
  • Curtis from Dreamgirls cheats and double deals his way to the top of the music industry but it all catches up to him. Deena turns against him and gives Effie evidence of his shady business deals which she uses to get exclusive rights to her hit single "One Night Only". Deena leaves him and the rest of The Dreams disband. Even though Curtis is trying to move on to a new artist, it's possible he'll never get the same success he once had.

    Visual Novels 

    Webcomics 
  • In Drowtales:
    • Sarv'swati Vel'Sharen works together with her sisters, Snadhya'rune and Zala'ess, to launch The Coup against their mother and kill her. This makes Sarv'swati the defacto leader of the Sharen clan, but destabilizes their empire and eventually provokes half of the clans into rebellion. By the time it's over, most of her children are dead and the throne room itself is under siege, with Sarv'swati breaking down in tears and begging the very mother she killed to come back.
    • The Big Bad, Snadhya'rune Vel'Sharen, enacts a series of schemes to ravage her city and make it collapse so that she can takeover uncontested. She is completely successful in ruining the city, and partially successful in taking over, but the city continues to fall apart beyond her control, leaving even her unhappy with how little there is left to rule.
  • The Order of the Stick:
    • The Start of Darkness prequel book shows this happening very, very heavily to Redcloak, who loses nearly everyone and everything he cares about as he tries to make progress on the quest his god has given him. It also happens to a lesser extent to Xykon, whose transformation into a lich has made him immortal and more powerful than ever... and becoming an undead also means that he has lost all the earthly pleasures that he had believed made life worthwhile before his transformation. (The loss of his sense of taste and ability to enjoy coffee being the one that gets emphasized by the book.)
    • Vaarsuvius's Deal with the Devil, literally harnessing the powers of evil, ultimately doesn't accomplish what they planned. In a twist, V's subsequent actions cause a LOT of change, some of it even good, but they're left morose at how badly things went awry. Thankfully, this has started V down some real character development.

    Web Original 
  • The final Act of Dr. Horrible's Sing-Along Blog, Joss Whedon's 2008 Web Original supervillain musical. Dr. Horrible/Billy attempts to kill Captain Hammer to both gain entry to the Evil League of Evil and win Penny's heart. In doing so, Billy indirectly causes Penny's death and Captain Hammer's humiliation. The final scenes show him living the high life of an A-List villain... but the final shot shows Billy, heart-broken and traumatized. And the final song describes that he has achieved everything he ever wanted, but the lyrics are dripping with double meanings: "The world I wanted at my feet": the world is my oyster, or Penny - the "world I wanted" - lying dead at his feet. It's also shown that all of this was strictly unnecessary; Penny thought Billy was attractive, and probably would have gone out with him had he asked her to. But Billy was so into the role of the Dogged Nice Guy that he loved the idea of Penny more than Penny herself, and never realized this until Penny was dead, leaving his schemes All for Nothing.
  • Bennett the Sage and JesuOtaku have done several crossover videos, with the idea in mind being Bennett attempting to Break or Corrupt the Cutie with terrible and sexually shocking or exploitative anime. In the third such crossover, JO reviews Master of Martial Hearts for Bennett, and he agrees that Sage has won and shown him something so gratuitously cruel and horrific that he just can't laugh it off or remain unaffected by it. However, after a relatively short spell of being horrified and depressed, JO remembers that it was just fiction and all the good things about real life, then goes outside to enjoy himself and cheer himself up by playing with his roommate's dog. Meanwhile, Sage is left in a deep depression with his "victory", pondering where mankind has gone wrong, and whether a species capable of such cruelty and darkness is worthy of redemption.
  • RWBY: Hits Cinder in Volume 5, as her mortal wounding of Weiss only succeeded in bringing out Jaune's healing Semblance and making the rest of the heroes double up their efforts. If that wasn't enough, her plan to ambush the children with Raven and Vernal and betray them to get the relic backfired, as Raven used Vernal as a decoy to get the relic for herself.

 
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Expecting A Happy Ending?

After Bugs' trick is revealed, Elmer becomes enraged and unleashes the full power of his magic helmet on Bugs with intent to kill. He succeeds, but comes to regret it.

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