"And when everything they have built lies shattered, I will savor their fall from the sky. For I have been patient."
Chessmasters in western animation TV.- Avatar: The Last Airbender:
- Azula of Avatar: The Last Airbender — The Vamp, Dragon Lady, Hero Killer, and Psycho for Hire all rolled into one.
- Her father, Evil Overlord Ozai, prefers the 'set the chessboard on fire and stand back laughing maniacally' approach, rather than messing about with all those fiddly little pieces. Until her Villainous Breakdown, Azula was a genuine (and, fortunately for Ozai, genuinely loyal) Chessmaster, so she got to do all the thinking.
Oh, Ozai can scheme fine (note the flashback in "Zuko Alone", where he very clearly exploits the weak spots of everyone around him to get exactly what he wants, and he managed to keep Azula under control for years — no mean feat!). Problem is, he's usually far too Drunk with Power to put that cunning to effective use.
Effectively, Azula plays this trope straight, using plots, her skills as a 'people-person' and good ol' situational awareness to deal with her enemies; kicking ass and taking names is more a trump card she keeps close to the vest. Ozai's cunning when he needs to be, but he is much more of an outright bully who uses violence, intimidation and raw displays of power to get his way. Ozai's the club, Azula's the rapier. - Long Feng is very good at this too, keeping a city under his control for years with no one but his immediate henchmen the wiser. Unfortunately, his flaws, like underestimating his opponents and not dealing well with sudden reversals — both of which Azula exploits....
- Her father, Evil Overlord Ozai, prefers the 'set the chessboard on fire and stand back laughing maniacally' approach, rather than messing about with all those fiddly little pieces. Until her Villainous Breakdown, Azula was a genuine (and, fortunately for Ozai, genuinely loyal) Chessmaster, so she got to do all the thinking.
- Amon, Big Bad of the first season of The Legend of Korra, has claimed himself to be a chessmaster. He has thus far been very convincing at his role. Episode 6 sealed his status as not only a brilliant Chessmaster, but also something more.
- Azula of Avatar: The Last Airbender — The Vamp, Dragon Lady, Hero Killer, and Psycho for Hire all rolled into one.
- Anarky, the Big Bad of Beware the Batman, loves to play chess using Batman and various villains as chess pieces, as symbolism for how he indirectly manipulates the events of the series.
- Lawrence Limburger had a couple of episodes playing several factions against each other in Biker Mice from Mars. This had to involve a chessboard with the people involved and a lot of Evil Laughter.
- Henry Haber from Bob's Burgers runs for school president under a chess-based platform, with him eventually winning the election not by popular vote, but rather by some crafty manipulation that involves Millie running for school president (and Louise, knowing full well of her Yandere interest in her, going all out to stop her).
- Vlad Masters of Danny Phantom is fond of using chess metaphors to describe his Evil Plan.
- Viren and his patron Aaravos from The Dragon Prince, especially when they combine their skills. Viren is an excellent people-person, able to twist any situation or person to his advantage. When Ezran told him to dismiss a large portion of the army, he still managed to phrase the order in a way that made the remaining army undyingly loyal to him. His charisma and persuasiveness is further bolstered by Aaravos, a chessmaster of highest sort but who's not in any position to be as active as Viren. Together, they walk straight into the Sunfire elf capital, knowing that the arrogant and traditionalist queen will insist on them going through a lethal "purification" ritual close to the source of sunfire elf power. Aaravos and Viren proceed to absorb said power and burn the queen to death.
- Dragons: Race to the Edge:
- Viggo Grimborn does this with "Maces and Talons", what appears to be its universe's version of chess (even though chess is also mentioned to exist as a separate game). He even spells this out when Hiccup arrives at his ship which is by then completely abandoned, save for a Maces and Talons board setup to reflect the current situation. Viggo uses complex plans involving Batman Gambits and Reverse Psychology and regularly speaks in "Maces and Talons" metaphors. He is pleased to discover that Hiccup is actually a Worthy Opponent .
- In the later seasons, we also have Trader Johann, who is revealed to have been Evil All Along and Obfuscating Stupidity for eight whole seasons to trick the Dragon Riders into playing into his hands repeatedly without them realising. It's only after Johann reveals himself that the Dragon Riders are able to put the pieces of his machinations together.
- Anti-Cosmo and HP on The Fairly Oddparents could both qualify, usually tricking Timmy or some other third party into helping with their plans.
- Spoofed in Futurama by Zapp Brannigan, who sees himself as a brilliant strategist and refers to chess to prove this, but keeps mixing it up with other games: "In the game of chess, you can never let your adversary see your pieces."
- Gargoyles:
- David Xanatos, king of the eponymous Xanatos Gambit. His girlfriend/wife Fox is no slouch at it to the point where almost all the events outside of the Trio's promotion competition in the episode, "Upgrade" is part of a special game of chess. This is done with the couple competing using a chessboard with board pieces representing each of the people they are manipulating; The Pack for Xanatos and the Manhattan Clan for Fox.
- Fox, Thailog, and the Weird Sisters all play close to Xanatos's own level (Thailog and Fox have even bested him once each).
- Demona does some of this, though she's often so hot blooded and/or generally screwed up that she'll inadvertently sabotage herself.
- The Archmage doesn't have the same skill as the above, but he makes up for it with the sheer grandiose nature of his ambitions.
- The Illuminati are implied to be a whole organization of these (at least, the ones at the top are). The Illuminati's status as an organization of these is established in the comics, where Xanatos is recognized for his cunning and manipulative skills and is inducted into the organization... at the lowest rank! The illuminati ranks run from 1 to 36, with each rank having that many members at that level (1 member is rank one, 2 members are rank two, and so on.). The person who is Rank 1 has thus outwitted 666 other chess masters to get there.
- Gravity Falls: Bill Cipher engineered events for at least the last thirty years, all to complete his plan of merging his world with the real world, freeing him and his other nightmare demons. This was just the final and first successfully completed plan in a long line of plans executed since, presumably, the beginning of the universe. Previous plans included convincing a shaman to try and build a portal long before it was technologically feasible. When the shaman found Bill out, he set himself on fire ("DRAMA QUEEN"). Also, the original intention for Ford's portal was simply a gateway for Bill and Co. to pass through which Ford thought was for his own research purposes before he also found Bill out. After Ford spent thirty years in various dimensions, breaking the Rift the portal created upon his return became the new plan. As a Visual Pun, he's seen playing chess with Ford. Ford also writes in code in the journal after he discovers Bill's trickery, "INTERDIMENSIONAL CHESS ISN'T FUN WHEN YOU'RE A PAWN."
- James McCullen makes a good attempt at being this in the G.I. Joe: Renegades episodes, playing the Joes and Cobra against each-other but gravely underestimates who it is he's really up against in Adam DeCobray.
- My Little Pony: Friendship Is Magic:
- The Big Good, Princess Celestia, seems to be able to play this part when necessary, and is a rare benevolent example, working for the good of her subjects. She remains somewhat enigmatic, but seems to have wisdom fitting her millennial experience of ruling. She generally seems on top of everything that's going on, but has twice been shown doing some serious plotting: At the beginning of the first season, she pulled off a Gambit Roulette with the twin goals to a) make her student Twilight Sparkle get out more and make some friends and b) save the world. In the beginning of the second season, she performs a much simpler and more elegant single-step Batman Gambit with somewhat similar goals.
- Celestia's old Arch-Enemy Discord — a being so dangerous and chaotically ingenious that he's actually able to catch her off balance and unnerve her — plays a round against her in "The Return of Harmony", with the main characters as pawns. (Although, if we're doing Chess Motifs, there's more than one reason why it might be fitting to call them Celestia's knights.note ) Discord's plan aims at making sure that the ponies will be psychologically broken and unable to use the only thing that can stop him even after they do find it, although given his power, it looks like he's also doing things the hard way just For the Evulz.
- Changeling Queen Chrysalis apparently planned an invasion of Canterlot (the pony capital) by deliberately scaring them to set up their defences, which only worked to her advantage when no-one knew she was already inside and working on something that would both give her great power and make sure the magical shields would fall at the right moment anyway. And then she takes another level in magnificent bastardry in the comics, where she hatches a scheme to suck all the magic out of Twilight Sparkle by fillynapping the Cutie Mark Crusaders to lure her to her Supervillain Lair, then capturing the rest of the Mane Six to coerce Twilight into studying The Dark Arts as her apprentice. Like Discord in the show, the only reason she loses this time is because she underestimates The Power of Friendship.
- Sorcerous Overlord King Sombra is largely considered the biggest example so far — at least before he became an Almighty Idiot World-Wrecking Wave, that is (and even then, he still shows signs of It Can Think). Case in point: He gets a Near-Villain Victory just because of the Crazy-Prepared measures he took over a millennium in advance. Oh, and the kicker? The Crystal Empire's past vanishing and present reappearance is because of his Dead Man's Switch-style curse allowing him to preserve "his" domain despite Celestia and Luna's initial defeat of him. When he's resurrected in the Season 9 finale, he doesn't have his Crazy-Prepared measures, but his cunning is on full display when he pulls of a complex plan where he attacks the Crystal Empire again, knowing that the heroes will bring the Elements of Harmony to stop him, and then fakes his defeat so that he can follow the heroes when they're returning the Elements to the Tree of Harmony. He then destroys the Tree, depriving the heroes of their greatest weapon, and then nearly succeeds in his real goal of conquering Canterlot.
- Cozy Glow, the Big Bad of Season 8. She puts up the facade that she's an innocent little filly for most of the season, then hatches her master plan. She knew that, once she started draining the magic of Equestria, the Mane Six would be sent to Tartarus to check on the most likely culprit (Tirek), allowing her to take over the School of Friendship (and even when Starlight Glimmer didn't go with them, she quickly disposed of her). When Obstructive Bureaucrat Chancellor Neighsay shows up, she manages to trick him into thinking she's helping him before betraying him by convincing the other students to revolt against him. Even when she gets defeated and ends up in Tartarus, she still seems to get what she wants–namely, close vicinity to her pen pal Tirek. While she isn't seen playing the game, she gets bonus points for her cutie mark being a chess piece (a rook, to be precise).
- The Owl House: What allowed Belos to stay in power, is his nightmarish planning skills. Beyond organizing a plan, seemingly for centuries, to ensure Luz teaches him the magic he'll need in the future, he's also organized the "Day of Unity" for quite some time, inducting every witch into a Coven so as to murder them all at once and take their power to achieve his own goals, proves to be Crazy-Prepared for betrayal multiple times over, and even proves to be a master of rearranging the plan when the time calls for it.
- Phineas and Ferb:
- The Supercomputer from Phineas and Ferb is a rare benevolent example. The Supercomputer is omniscient and will answer any question given to him. Phineas and the gang ask him "What is the nicest thing we can do for Mom today?" and Candace asks him "How can I get my Mom to see what my brothers have done?" The Computer has Phineas and the kids go to Danville Hill with a leaf blower and a container of dye tied to balloons, and has Candace build a device with a toaster and a mirror. The end result is Phineas' party ended up undoing Linda's bad haircut, and Candace's device showed her what happened.
- And another benevolent example, from the Christmas Special, is Santa Claus himself, sending Doofenshmirtz the plans for a Naughty-inator, marking all of Danville as naughty, and giving Phineas and Ferb their Christmas gift of getting to experience what it's like to be him. He even foiled Doofenshmirtz with a CD that was given to Perry as a Secret Santa gift, containing a song with a note that shattered vital parts of the inator. And said foiling fulfilled Doof's Christmas wish, giving him the ability to hate Christmas like a normal villain instead of having intensely burning apathy.
- HP's thirty-seven year plan from School's Out! The Musical. After the Pixies discovered the abandoned clown baby Flappy Bob, they raised him to become a boring corporate executive and inspired him to build an educational camp/day care center called the Learn-a-Torium. At the start of the summer, the pixies sabotaged the kids' summer plans to cause Dimmsdale to be destroyed, which allowed Bob to rally support from the town for his "Camp Learn-a-Torium". The kids were sent there and HP convinced Timmy to wish for a world ruled by kids, eventually making them so happy that they don't need fairies anymore, forcing Jorgen to recall them all back to Fairy World. Finally, the Pixies convinced Bob to sign over control of Fairy World in exchange for him taking back control of Earth. However, the plan all unravels when Bob overhears the pixies celebrating their plan and admitting they never genuinely cared for their godson. Feeling betrayed, he decides that Timmy had a point about him betraying his own values in a quest for power and decides that the world should go back to the way it should be.
- Subverted in an episode of The Simpsons where Mr. Burns hires an assassin to kill Grandpa. After two botched attempts, the assassin suggests a third option which he describes "as complex and precise as a well-played game of chess." Cut to him bursting into the retirement home with a machine gun and firing wildly in all directions.
- Skylanders Academy: Despite being sealed within Kaossandra’s Evil Spell Book, Strykore, Master Eon’s Evil Twin, made a plan at the end of the second season that involved using the Doom Raiders’ vendetta against Kaos and his mother to get Kaos to meet him. This not only allowed Strykore to be freed from his prison, but he also destroyed the trust that had been built between Kaos and his mother by claiming to be the former's father and that his mother betrayed him.
- South Park:
- Eric Cartman is the chessmaster in quite a few episodes. "Scott Tenorman Must Die" is the most chilling example. Even the main group acknowledges how dangerous Cartman is here. To add to it, he even uses Stan and Kyle to rat out his (fake) plan to Scott Tenorman. So beyond everything, everyone knew Cartman was up to something. He just took it to the next level.
- Kyle Broflovski's also shown to be quite capable of this, usually as direct opposition to Cartman. This is best seen in "Le Petit Tourettes" where he orchestrates a series of events to stop Cartman's faking of the disorder.
- The terrorist cell in the Imaginationland trilogy, who orchestrate a war between the Good and Evil characters who were at peace on their separate territories of Imagination, and in order to wipe them all out and destroy collective imagination, even posthumously as they were killed after they started the war. However, the Good characters get full support in the narrative as if the Evil characters, despite being Obviously Evil, were the Big Bads, but neither side were responsible for the war. Also, the gambit failed when Good characters won the war with all their casualties resurrected, while the Evil characters weren't so lucky and their survivors were imprisoned. And the real perpetrators of the war were already dead right after the war started.
- Played with in "Mystery of The Urinal Deuce". The episode focuses on the true culprit of 9/11. Stan and Kyle visit a 9/11 truther who claims the government planned it in order to invade the Middle East. Suddenly, a SWAT team captures the three and takes them to the White House, where George Bush personally executes the truther, and tells the boys how they caused 9/11 in "most intricate and flawlessly executed plan ever", before attempting to execute them. They miss, and both boys flee to Chicago. Then it turns out the government didn't plan 9/11. However, he knew there would be conspiracy theorists who would accuse them anyways, so they created the 9/11 Truth Movement to feed that crowd and give the government an illusion of power.
- Leslie Meyers turns out to be one as well. She exploited the Politically Correct movement to gentry South Park so that the price of living there would increase to the the point where the townsfolk can't afford to live there forcing them move out while allowing her race of sentient Ads to take over. She had done this to many towns beforehand and would repeat this process until even the planet itself is too expensive to live in.
- Lennart Bedrager is one where he reveals to Gerald that he successfully drove the entire world into chaos through manipulation alone. His reason for doing all this, because he thought it'd be funny to do so.
- Toffee from Star vs. the Forces of Evil. He infiltrates Ludo's group as he is the monster that aims for the wand the most. He gains Ludo's absolute trust and uses that trust to use Ludo's minions, moving them around to get as much information on Star and her wand as he can. He then makes Ludo banish his previous loyal dragon Buff Frog. Then he causes a revolt among the minions which results in Ludo being thrown out of his own castle, making Toffee the new group leader. And the absolute masterpiece of the entire thing? He doesn't want the wand. He has no interest in owning and using it. He asks Star to destroy it. And everything he had done was so he could force her in a situation where she must obey him. He also alludes that he possibly knows most of Star's family secrets as he knew exactly how Star could destroy the wand, while she didn't. Oh yeah, and as cherry on top: during that confrontation the destruction of the wand causes a massive explosion. And Toffee leans back in satisfaction, only a few steps away and watches the wand go off, having been fully aware that this would happen as well. But wait, there's more! The Season 2 finale reveals that Toffee didn't perish in the explosion. No, the reason he wanted the wand destroyed was so that he could use the explosion to merge with the wand, from which he manipulated everything Star and Ludo (having found half of the wand) did throughout the entire season, while at the same time, corrupted the wand's magic. Then after Star realized the truth and used the Whispering Spell again to remove him from the wands, this turned out to be what Toffee wanted as well, using it to trap Star in the wand so he could force her mother to return the lost finger she had taken from him, thus finally allowing him to completely restore his body. Even in his final moments, Toffee hinted that everything was still going as he planned.
- Just like in the old Legends continuity, Grand Admiral Thrawn is a force to be reckoned with when it comes to planning and tactics in Star Wars Rebels. He manages to nigh effortlessly manipulate the rebels of Phoenix Squadron into doing what he wants, only ever losing due to variables he couldn't possibly have planned for.
- The Brain from Teen Titans (2003) plans out all of his moves like a chess game and his mobile body even LOOKS like a giant chess piece! The final battle against the Brain's Brotherhood of Evil actually takes place in a large room that resembles a gigantic chessboard.
- Transformers:
- Megatron of Beast Wars (and later Beast Machines), nearly ended the Beast Wars several times without leaving his hot tub. His ultimate weapon in the Grand Finale was, in fact, unwittingly furnished by an especially treacherous minion.
- This role almost equally describes Tarantulas — who was a third party in and of himself, only pretending to work with the Predacons. He frequently even pulled one over on Megatron. At one point Megatron was sitting in his throne all impressed with how brilliant he was because he managed to a way to spy on Blackarachnia... and then we cut to Tarantulas spying on 'him.'
- Tankor, of all characters, became one in Beast Machines after his spark was reawoken.
- W.I.T.C.H.:
- Nerissa from W.I.T.C.H.'s second season is excellent at this. Her opposition is so thoroughly manipulated and played that despite the heroines' best efforts, they can only score the smallest of victories in comparison to her Magnificent Bastardry until the absolute end of the season... and were only then able to overcome it because Phobos is also good at chess and moved Nerissa into being absorb into her own Seal.
- And then we find out that Will was manipulating Phobos like a fiddle, expecting him to betray them as soon as he had the Seal of Nerissa and easily putting him in a situation in which he would be defeated.
- The adaptation of Dick Grayson/Robin/Nightwing in Young Justice (2010) is a benevolent form of this. He engineers a fake mission from Batman to help out the circus he was raised in in Season 1, while in Season 2 he makes a complex plan involving a false case of teammate gone bad, a faked death, and more, which ultimately results in the two factions of bad guy turning against each other
