Darker Than Black: The elusive, mysterious Amber betrayed MI-6 to work for The Syndicate, eventually leading the deadliest squad of Contractors in Heaven's War. Realizing the Syndicate's true intentions and using her powers to see and rewind the future countless times, Amber manipulated the Syndicate and her own side to seal off Heaven's Gate, which caused a massive disaster that rendered most of South America uninhabitable. Returning in modern day Japan, Amber orchestrates a series of bombings while kidnapping the scientist behind the Saturn Ring project, manipulating her former lover Hei and the world's intelligence agencies to place Hei close to Hell's Gate so he can seal it as well and prevent the Saturn Ring project from killing all the world's Contractors. After settling things with Hei, Amber sacrifices herself to rewind time and give him a chance to choose a third option, later revealing she had foreseen that possibility and left guidance in the new world Hei had made.
ERASED: Gaku Yashiro is a psychopathic mastermind who brings excitement into his everyday life by murdering children and expertly framing Innocents for the crimes. His genius extending all the way to childhood, where he effortlessly murdered his abusive older brother and made it look like a suicide, he carries his depraved intelligence into adulthood, where he spends years perfecting the art of charming and manipulating others, especially his preferred targets. Be it noticing signs of abuse or taking advantage of their innate naivety, he always gets his target, and in a notable instance, murdered one of his male students who resembled a girl, knowing it would eliminate him from suspicion as a killer who solely targeted females. Despite Satoru's time travel abilities, Yashiro one-ups and outwits him at every turn, never even knowing of the man's powers, just being so naturally adaptable that nothing slows him down. Yashiro is a truly terrifying killer, having not only the smarts and charms to kill whoever he wants with ease, but also the fast-thinking to ensure that he's never caught, no matter what opposition arises.
Gankutsuou: Once an innocent man sentenced unjustly, Edmond Dantes returns as the ruthless, charming Count of Monte Cristo to destroy his enemies. Rescuing the son of his former best friend Fernand and his fiancee Mercedes, the young Albert Morcerf, it is later revealed the Count set up the kidnapping to begin with to gain Albert's trust. Manipulating his old enemies into trusting him with investments that ruin them, the Count also reveals he rescued a young alien girl named Haydee so she could expose Fernand as a traitor and the murderer of her father. Edmond also introduces one enemy, Villefort's, mentally unstable wife to poison so she will commit murders and further disgrace her husband while later having his ally, the bandit Andrea, reveal he is Villefort's illegitimate son to ruin him further. Finally, the Count plans to harden his own heart and kill Albert to destroy Fernand, not satisfied until he has given Fernand the same unending despair Fernand once gave him, before finally letting go of his hatred thanks to the love of Albert, ending his life with a final plea to remember that his name was Edmond Dantes. A charming, sophisticated manipulator, none around him ever saw the Count coming until he struck.
Golgo 13: Master assassin Duke Togo, better known as Golgo 13, spends most of his stories coming up with a complex gambit to fool his target and get him in a position to take his shot. A master sniper, Togo has been active decades with incredibly few failures and a sterling reputation as a professional. In one instance, he tricked a CIA traitor into leading him to her boss while wearing a red coat against the snowy background to snipe them both in one shot. In another, knowing a mobster was faster on the draw than him, Golgo fooled him into being occupied with his dominant arm holding on to a woman so Golgo could outdraw him. Throughout every story, what characterizes Golgo 13 is cold charisma and unreadable expression, always having a plan to take out his target, no matter who it is.
Gundam: In a franchise featuring endless wars, these villains truly stand out for their charisma and intelligence in the field of battle:
Mobile Suit Gundam: Kycilia Zabi was the last member of her family standing for a reason. Fully aware of her elder brother Gihren's moral depravity and mismanagement of the conflict with the Earth Federation, Kycilia uses the One Year War as a cover for a coup d'etat against him, gathering resources and allies, while undermining Gihren's loyalists. Upon discovering through Colonel Killing's betrayal that Gihren had infiltrated her faction and was preparing to frame her for treason, Kycilia moved swiftly, leaking Char's identity to Gihren's fake conspirators and transforming a sham plot into an actual revolt against his rule. Aware that Zeon could no longer win the war, and that the Federation would never make peace while her brother lived, Kycilia journeyed to A Baoa Qu and, on finding out that Gihren had murdered their father, executed him for patricide and assumed command of what was left of Zeon. Killed when Char Aznable erratically and irrationally betrayed her, Kycilia was nevertheless the only Zabi, or indeed, Zeon Admiral, with both a realistic appreciation of their circumstances, and the ruthlessness and will to act accordingly.
Mobile Suit Zeta Gundam: Titans Lieutenant Paptimus Scirocco is an Enigmatic Minion who graduates to taking over the organization. A brilliant tactician both in and out of a mobile suit, Scirocco excels at reading potential in his subordinates and outmaneuvers the Anti-Earth Union Group (AEUG) to capture the strategic base of the lunar city Von Braun. Leaving the operating of Von Braun in the hands of his antagonistic superior, Scirocco leaks the man's plans to the AEUG and arranges for his death to gain more power within the Titans for himself. Forming an alliance with Haman Khan of Neo Zeon, Scirocco bolsters the strength of the dying Titans with her army. To take power, Scirocco personally assassinates their leader, Jamitov Hymem, taking over the Titans and blaming Jamitov's death on Haman, rallying his forces to fight against her. Giving a former AEUG pilot he corrupted to his side a grand speech on his ambitions for humanity, Scirocco engages the AEUG personally and reveals he has kept his alliance with Haman to revitalize the strength of his forces. Even with his forces destroyed by the blast of a colony laser, Scirocco continues to fight Kamille personally and in his dying moments, destroys Kamille's mind, unwilling to accept defeat. Emotionally manipulative but charming and stylish, Scirocco proves himself to be every bit as deadly and cunning as he is mysterious.
Mobile Suit Gundam ZZ: Axis warlord and Neo-Zeon Regent for Life Haman Khan came closer to conquering the Earth Sphere than any of the despots to come before or after her in the UC timeline. Intervening in Zeta Gundam's Gryps Conflict on the side of Paptimus Scirocco's Titans, Haman helped turn the battle between the AEUG and the Titans into a full scale civil war within the Earth Federation, a war from which she emerged as the one true winner following Scirocco's death and the obliteration of the Titans and most of the AEUG. Invading the Earth before the Federation could recover from the war, Haman occupied huge swathes of the planet, and used the Dublin Colony Drop to terrorize Federation officials into surrendering to her, all while employing sheer force of personality to mask her myriad personal issues and hold the backstabbing house of cards that was Axis-Zeon together. Betrayed at the zenith of her power by Glemmy Toto, and faced with internal rebellion by his supporters, Haman quickly moved to quell the descent, meeting Glemmy in open battle. Confronted by series' protagonist Judau Ashta, Haman was persuaded that humanity did not, in fact, need her jackboot on its throat to stop them from killing each other. The only UC Big Bad self-aware enough to come to grips with what she had become, Haman killed herself in the name of giving the world a better future.
∀ Gundam: Guin Sard Lineford is the former lord of the Principality of Inglessa, falling into disgrace with the defeat of his country, though managing to keep his influence thanks to his friendship with the Luziannan princess Lily Borjano. A young, ambitious and visionary lord, Guin successfully leads the forces of Earth against the technologically advanced Moonrace and study their advanced weapons. One of the heroes' smartest allies, Guin eventually betrays them to join Gym Ghingham, taking a role as the leader of a new technological revolution, which only fails because of the barbaric behaviour of the latter. Accepting his defeat at the hands of his former friend and political ally, Lily, Guin saves the protegee of Gym and escapes with her.
Mobile Suit Gundam SEED: No one hides their true intentions quite like Rau Le Creuset, ZAFT Commander and defective clone. Lacking his own sense of identity, and seeing the face of his "father" every time he looks in the mirror, Le Creuset believes the rest of humanity is suffering just as much as he is, and sets out to put the entire species out of its misery. Playing the role of Patrick Zala's right-hand man, Le Creuset sells ZAFT secrets to Blue Cosmos headman Muruta Azrael, prolonging the Bloody Valentine War, and ensuring that the conflict ends with mutual attempts at genocide, as Azrael tries to nuke the ZAFT colonies and Patrick fires his Wave Motion Gun at Earth. Successful at masking his encroaching madness until the very end, Le Creuset dies smiling, convinced that the entire world will shortly be following after him.
Gundam SEED Destiny: ZAFT Chairman Gilbert Durandal sees himself as the saviour of Earth and nearly persuaded most of the planet to go along with it. Presenting himself as a moderate and a pacifist, Durandal made use of Lord Djibril and Blue Cosmos' blatant evil to launch an invasion of the Earth Sphere disguised as a liberation, using his own reputation for honesty and the services of Lacus Clyne impersonator Meer Campbell to camouflage his intentions, and scattering agents of FAITH throughout the ZAFT military to keep an eye on its loyalty. Preying on the emotional insecurities of those in his service, Durandal turned Decoy Protagonist Shinn Auska into the very thing he hated most, and kept veteran characters like Kira, Athrun, and Lacus out of the picture or unsure if they should oppose him for most of the series. Only killed when he loses the faith of his most loyal enforcer, Rey, Durandal dies convinced that he was right and that without his Destiniy Plan the world is doomed.
Mobile Suit Gundam: Iron-Blooded Orphans: Rustal Elion is one of the Seven Stars who lead the military police force Gjallarhorn. A charismatic nobleman and brilliant military strategist, Rustal has the complete trust of his subordinates. When Rustal's rival in the Seven Stars, McGillis, moves against him, Rustal engineers a small scale war to turn McGillis' allies, Tekkadan, against McGillis. While the war fails to break McGillis and Tekkadan's alliance, it does force Tekkadan to shut down their Earth branch, weakening the organization considerably. When the tensions between Rustal and McGillis lead to civil war, Rustal has one of his subordinates infiltrate McGillis' forces, fire an illegal Dainsleif railgun at Rustal's fleet and commit suicide, giving Rustal justification to annihilate McGillis and Tekkadan. While political tensions ultimately force the Seven Stars to disband in favor of democratically elected leaders, Rustal still comes out ahead as he is elected leader of Gjallarhorn. Rustal remains a hero to the public and becomes the first Big Bad of the franchise to win in the end.
Hunter × Hunter: Leader of the Phantom Troupe, also known as the Spiders, Chrollo Lucilfer is a handsome, charismatic young man who masterminds elaborate heists and mass murders, only to get bored of the objects he obtains and sells them away again. Coming to the mafia-ruled Yorknew City, Chrollo masterminds the heist of the century where the Spiders infiltrate the mob and steal all the items from a high profile auction while Chrollo targets and steals the power of one mob leader's daughter. Completely outwitting the mob, Chrollo learns there is a contract on his head from the Twelve Godfathers and instantly hires different members of the same assassin family to target the Godfathers before having the Spiders fake their deaths and escape completely free. Chrollo also deeply values the other members of the Troupe, offering the lives of multiple mafia soldiers as a "requiem" for the fallen Uvogin, and when he faces off with the ruthless killer Hisoka, he also shows what a brilliant tactician and combatant he truly is by completely outplaying and seemingly killing the skilled fighter. A charming, philosophical man who freely admits he places no value on his own life, Chrollo is one of the most memorable villains in all of Hunter x Hunter.
Jackals: Lee Meilang, the head of Tennouren, is the most intelligent and devious gangster in all of Cicero City who takes over Tennouren solely to destroy the gangs in the city and come out ahead. Meilang manipulates their rival mob Gabriella into a war where she proceeds to play the hero Nichol Heyward and his allies into doing everything she wants. When Don Salieri is overthrown by his depraved underling Vampire Franco, Meilang simply works it into her plans and comes out ahead, selling out the other gangs and establishing a legitimate organization with the government after their defeat, completely untouchable to the end.
Kindaichi Case Files: The Gentleman Thief is really a cunning woman and Master of Disguise with a penchant for stealing precious items and leaving notes to her next targets. Disguising herself as a young journalist, Diago Maki, the Thief targets Gamou Gouzou's residence to steal his painting, "My Beloved Daughter". Although almost outwitted by Kindaichi, the Thief disguises herself as and old woman and ties him to a basket of heavy rocks, leaving him stranded in the middle of a busy street. Later appearances show the Thief uses the same ploy to trick Kindaichi and get away with her stolen goods, saying she hopes to meet her challenging rival again.
Legend of Galactic Heroes: Paul von Oberstein is the most ruthless of Reinhard von Lohengramm's inner circle. A man infamous for his Dissonant Serenity and ruthlessly pragmatic advice, Oberstein devotes himself fully to Reinhard and his new dynasty, using his tactical and political brilliance to help entrench Reinhard as the rightful ruler of the crumbling Empire. Seeking to destroy the Goldenbaum dynasty, Oberstein hears that its mad prince Braunschweig is planning to nuke the rebellious colony Westmoreland, and intentionally delays Reinhard from hearing the news to let the attack happen. This has the effect of the entire empire unifying around Reinhard in revulsion, just as Oberstein planned. Oberstein makes himself a hated figure to keep any loathing directed from Reinhard, manipulating other admirals as he sees fit to keep Reinhard's empire safe and even uses himself as bait to lure out the last of the Terran cultists in the final episode to eliminate the final threat to Reinhard's rule, seemingly aware the empire he has forged has no place for him.
Lupin III, the titular thief, is a debonair rogue always ready with a plan for a brand new caper. A thief who savors the rush and thrill of the theft far more than any monetary value, Lupin also delights in paying karmic justice to deserving victims. Throughout multiple anime incarnations, Lupin is characterized by choosing seemingly impossible ventures or is thrust into inescapable situations, only to execute a cunning plan and escape completely free, in one instance even outsmarting an ancient brain supposedly beyond any human being's. Rarely ever losing his playful grin, and always ready with witty repartee, Lupin remains one of anime's most successful examples of a Gentleman Thief who is constantly capable of twisting a situation to his advantage.
Lupin's occasional lover, rival and ally, Fujiko Mine, is his equal in brilliance and audaciousness. A skilled thief who lives for the rush of the theft, Fujiko is able to perform as many complex schemes as Lupin while constantly outwitting him and everyone around her to get her big score. In one instance in The Woman Called Fujiko Mine, she poses as a tutor at an all girls' school, allows one girl to seduce her, only to reveal she knew the girl was a cop in disguise, to fool him and steal the codes she needed. Equally capable of ruthlessness, Fujiko once escaped prison by seducing a guard and sending him to execution in her place, never hesitating to weaponize her sexuality. At the end, Fujiko allows nobody but her to define herself and stops at nothing to achieve her goals, no matter who she has to manipulate or fool, while always maintaining the same charismatic style as Lupin himself.
My Hero Academia: 'Sensei', better known as All For One, is a incredibly powerful villain, the arch-nemesis of the heroic All Might. Secretly ruling the country from the shadows for generations, All For One was seemingly killed by his enemy, but survived and rebuilt a group of villains in secret. Wanting to hurt All Might, All For One tracked down All Might's mentor's long-lost grandson, and raised him as the villain Shigaraki tomura, knowing this revelation would be the one thing to crush All Might's heroic spirit. Even in his final battle with All Might, All for One is pleased even if he loses, knowing his loss will inspire Tomura to become the greatest villain in history to oppose All Might's own successor.
Lord Laertes Van Di Montague from Romeo X Juliet, who pretty much rose from the slums after the death of his prostitute mother, infiltrated himself in the Montague clan as a kid, killed its leader when he was of age, slaughtered the rival clan of the Capulets both to gain power and as revenge for his destitute origins, and ruled Neo Verona with a hand of steel for almost 15 years. And that's just the beginning...
Rurouni Kenshin: Ruthless Social Darwinist Makoto Shishio was once the feared Hitokiri of the Shadows during the Bakumatsu. Betrayed by the government and left for dead, Shishio survived and by virtue of his overwhelming power and charisma creates a powerful organization consisting of loyal soldiers he effortlessly manipulates, with one named Usui even ostensibly wanting revenge against Shishio for blinding him, unaware Shishio is well aware he's lost all hope of vengeance and is just manipulating him by using his pride. Shishio then sets up a complex plan to burn Tokyo, only for it to be revealed this is a ruse as he attacks Kyoto instead. Despite being foiled here, Shishio proceeds to have the heroes fight his men in single matches, all for the purposes of weakening or eliminating them before they face Shishio himself when he gains greater understanding of their abilities through the fights. Even after his defeat and death, Shishio shows no sign of complaint and instantly sets off with his deceased lover and most loyal follower to begin conquering Hell itself.
Slayers: Xellos the Trickster Priest is a Mazoku, and the most mysterious member of the cast. Hiding his true self behind a veil of smiles and pleasantries, Xellos ruthlessly manipulates Lina and friends into carrying out his wishes and destroying his enemies. Frequently arranging situations to benefit himself no matter what the outcome, Xellos helps destroy his Mistress, the Grand Beast Zelas Metallium's rivals and other Mazoku should it benefit him. Xellos tends to change his schemes on the fly as well, making it impossible to tell what was part of his plans from the start, even if he admits he feels some affection for Lina and her team. Xellos is so charming and affable, it's very easy to forget that he is a demonic being under his friendliness.
Space Battleship Yamato: Albelt Dessler is the charming, sophisticated supreme ruler and dictator of Gamillas. Desiring a peace in the galaxy through ultimate control, Dessler has expanded the Gamillas empire but keeps new conquered races happy by allowing them to prove themselves equal citizens in the empire on pure merit. When earth proves more difficult to conquer, Dessler deals with the matter by assigning a failed commander to either give Dessler more knowledge of the earthlings' tactics, or removing an incompetent without him lifting a finger. Dessler also outplays any who attempt to usurp his authority and when defeated, he promptly reemerges to take the Yamato over to restore himself to glory, convinced that his success is the glory of Gamillas itself.
Speed Grapher: Choji Suitengu is a man who flaunts his extensive wealth via using expensive yen notes as cigars, believing everything 'has its price,' especially human life. In truth, Suitengu is dedicated to overthrowing the social order of Japan, manipulating all the upper echelons of society with his Roppongi Club that caters to a variety of fetishes. Constantly planning ahead of series hero Saiga, Suitengu also manipulates his lover, Shinzen of the powerful Tennozou Group and later disposes of her when she attempts to betray and kill him.Revealing his tragic past to his arch enemy, the prime minister, when the man tries to kill Suitengu and take over the Roppongi Club, Suitengu kills him and enacts his master plan: completely erasing the corrupt upper class and causing a massive financial crisis to completely break their hold on Japan forever.
Sword Art Online: SAO designer Akihiko Kayaba, a pioneer in the field of Virtual Reality (VR), traps 10,000 players inside his game, killing them in the real world if they die in the VR one. Disguising himself as Big Good Heathcliff and guiding the players through the dungeon floors of Aincrad, Kayaba intends to betray and kill them in the last dungeon, acting as the Final Boss of his own game. When Kirito is able to deduce "Heathcliff's" true identity, Kayaba praises the boy for his observance before challenging him to a duel, promising to end the game of Kirito wins. Keeping his word and freeing the players, Kayaba seemingly commits suicide, though actually copying his Fluctlight onto the internet to continue existing. Reappearing in the next arc, Kayaba helps Kirito defeat the Arc Villain, Sugou, whom even he finds repellent. Entrusting Kirito with his last invention, Kayaba encourages him to go on to share it with the world, leading to the creation of many innovative VR games. Though utterly sociopathic, Kayaba never strayed from his strict moral code and stood out as one of Kirito's most noble foes.
Vinland Saga: Askeladd Olafson introduces himself to the audience sacking a fort and robbing it of its riches with a series of clever schemes, barely shedding a drop of blood. Leader of a group of Viking raiders, Askeladd was born the son of a slave and a lord. Murdering his father years later after his mother's death, Askeladd framed one of his brothers after ingratiating himself to his family. Playing the cutthroat court of King Sweyn with clever gambits, Askeladd has the caretaker of the weak prince Canute murdered to build Canute into an ideal candidate for the throne. Also driven by his desire to protect his maternal homeland of Wales, Askeladd finds himself briefly outplayed by Sweyn who demands he kill Canute or see Wales invaded by the Danes. Askeladd instead chooses to kill Sweyn and allow Canute to kill him, achieving all his goals posthumously by making Canute a beloved, respected King and knowing the young man will forge Askeladd's ideal kingdom and defend Wales out of gratitude.
Yu-Gi-Oh!: Maximillion Pegasus was the series' first genuine Big Bad and one of its most fondly remembered. The inventor of Duel Monsters and CEO of Industrial Illusions, Pegasus used the mind reading powers of his Millennium Eye to control the few things his billions of dollars could not, and planned to use KaibaCorp technology and Yugi's Millennium Puzzle to resurrect his deceased wife. Stealing the souls of Yugi's grandfather and of Mokuba Kaiba, Pegasus lured Yugi and Seto Kaiba to his Duelist Kingdom Tournament, where he pitted them against one another and his handpicked team of Eliminators, using Kaiba as a catspaw to damage Yugi's confidence before claiming the former World Champion's soul as well. Only narrowly defeated by Yugi & Yami's tag-team dueling strategy, Pegasus set a high bar for subsequent villains to aspire to, and whether as a duelist, corporate raider, or user of Shadow magic, always seemed to be holding all the cards.
Sakyo is a charming, charismatic member of the Black Black Club who came up from nothing. A born sociopath who despised his honest, loving family, Sakyo graduated from torturing animals into high stakes gambling where he amassed a fortune to join the demon-trafficking and torturing Black Black Club. Deciding to advance even further, Sakyo plays the group's founder Gonzo Tarukane by secretly paying off the Toguro brothers when Tarukane hires them as bodyguards, rigging the gambles he makes with Tarukane by having the Toguro brothers take a dive against Team Urameshi. Setting up his team to fight in the Dark Tournament, Sakyo takes a curious liking to Shizuru Kuwabara and protects her during the events while also manipulating and eventually disposing of the rest of the Black Black Club, before gambling his own life on Toguro's victory in order to insure he can see a portal opened to the Demon World out of sheer morbid curiosity. When Toguro is defeated, Sakyo immediately offers his life without complaint, bidding a last fond farewell to Shizuru first.
The Younger Toguro brother sold his soul 50 years go to become a powerful demon after winning the Dark Tournament in despair over the deaths of his students and the knowledge of his impending mortality. In present, having grown disillusioned with his life, he manipulates the events with Gonzo Tarukane to see if Yusuke Urameshi is a worthy adversary and forces him and team to join the Dark Tournament. Toguro manipulates Yusuke into becoming stronger while also keeping him from making Toguro's mistakes before the final match. After killing Yusuke's mentor, his former teammate and lover Genkai, Toguro is dissatisfied with Yusuke's strength and seemingly murders his friend Kuwabara to force him to fight all out, only to reveal he faked Kuwabara's death. Unlike his twisted elder brother, Toguro never sold his pride along with his soul and displays a true sense of honor, grateful to give his all against a final worthy adversary.
The 'Black Angel, Shinobu Sensui was once a brilliant young Spirit Detective whose idealistic view of humans was shattered by the Black Black Club. Years later, he uses the depraved Chapter Black tape to recruit a group of psychics to his side as Team Urameshi goes after him, manipulating all his enemies and allies alike to achieve his goals and weaken Yusuke's team. In one instance, Sensui forces Kurama to duel in a game against a little boy, with the boy not knowing he will die if he loses. Sensui is aware Kurama will do it, but knows it will shake him up too much to be of use in fighting Sensui at his best later, while also knowing a guilt-stricken Koenma will use up too much power restoring the boy to life. Sensui also uses his multiple personalities to bear the burdens of his crimes, revealing his true self in time to defeat and even kill Yusuke before opening a path to the demon world. His true goal? Is an elaborate suicide attempt to die at the hands of a powerful demon to atone for taking so many demon lives in the past. Passing as a dark mirror to Yusuke himself, Sensui remains one of his most sympathetic and fascinating enemies.