Trickster doesn't even begin to describe this character. If The Chessmaster is the master manipulator of events, the Manipulative Bastard is the master manipulator of emotions and perspectives. This is the guy who gets off on playing head games — clever and dangerous and lacking comedic overtones. He or she always has The Plan, but rather than do any work, the Manipulative Bastard prefers to play on other characters' emotions and then watch the victims destroy themselves as they waste their energy on fighting against fake dangers or their friends.
In many cases the Manipulative Bastard personally is rarely emotional and seldom burdened by notions such as empathy, yet is all too willing to abuse it in others. The Bastard is unmoved by the pain of others, if not actively basking in it. Thus the frequent association of how someone who does manipulative bastardry too often can come across as a sociopath. After all, too many Pet the Dog moments may lead this character to become the mask and care about the people he or she previously saw as playthings.
Like Chessmasters, Manipulative Bastards will have some larger scheme in mind but tend to lose sight of it more easily and simply enjoy the control they have over their peers. A highly-focused/ambitious Manipulative Bastard is scary indeed; not only achieving his or her goal, but then ensuring permanent supremacy by destroying the souls of everyone he or she used to get there. A hell of a lot of Heroic Willpower, and often Shooting The Dog is required to topple this character.
While this character type seems inherently villainous, many of them are at least nominally on the heroes' side. A cunning branch of the Anti-Hero family sports this trope and many a Guile Hero uses many of the same tricks. Indeed, many Tricksters also overlap into Manipulative Bastard territory. The hero will probably survive a relationship with this character, but their trust in people will not.
Manipulative Bastards often fall into the Karma Houdini trope — after all, they never "forced" anybody to do anything...which leads the audience to scream, "Why do you keep falling for this?" at the other characters.
Different methods of Manipulative Bastardry exists, depending on these characters' favorite tricks to manipulate people:
The last subtype is the Apparently Powerless Puppetmaster who is genuinely powerless and only has as much power as his/her opponents see fit to give him/her. To this end, he/she fakes stupidity or insanity so that he/she can avoid being assassinated while still being able to manipulate events as he/she pleases.
The Writer is the ultimate example of this. He manipulates everything in the entire universe.
Lupin III/Assassin in Just An Unorthodox Thief. Here, Lupin has become much more manipulative in dealing with his enemies, pushing Kirei to a path with seemingly innocent questions, playing mind-games against Saber, and manipulating everyone for his own benefit.
Loki in Child Of The Storm. He has performed a Heel-Face Turn, true, and he does regret his actions. But that just makes him Reformed Not Tamed, and within less than two years, he's built up a worldwide spy network in such a way that any attempt to uproot it by SHIELD would look like a wanton global case of Kick the Dog, rehabilitated himself as a sincerely regretful philanthropist, philosopher, superhero and a champion of the underdog, and now, a kindly uncle. Everyone thinks that he's nice and friendly. He is. But what they don't know is that's not all he is...
The Other Girl in the Hooker!verse. She's successfully ruining her other personality's (Penny) life, she gleefully mindfucks the Critic and Chick, and Linkara falls into her trap when she pretends to be Penny and be a crying mess.
Torment in the Spyro Madness Saga. As Cynder's Super-Powered Evil Side, she knows everything about Cynder and pretends to be her friend, but what she's really trying to do is possess her. As the manifestation of Cynder's darkness, she's fueled by the dark counterpart of what Cynder desires. Since Cynder has repressed feelings for Spyro, Torment tries to turn that love into lust. She temporarily succeeds and slaughters everyone at a party, causing Cynder to suffer a collosal Heroic BSOD.
Red Cyclone's masterful manipulation of the entire Griffin Army in Ace Combat The Equestrian War. Even his companion, Black Star, apparently fell for his tricks.
Bowser, Eugene, and Lucy have all had their moments in Calvin At Camp.
Harmony Theory: Max Cash, with a little help from a couple of Elements of Harmony.
Dumbledore is even more manipulative in Knowledge is Power than he is in canon, but less effective. Lord Potter is effective at manipulation, but often prefers just to shout and swear at everyone until they back down.
An Alternate Keitaro Urashima features Granny Hina as its primary antagonist. In her case, many of her manipulations have been derailed due to Keitaro refusing to play along — and making sure his family and friends are aware of her true nature. However, she manages to keep stringing along her tenants, as well as having Ryuichi completely convinced that she's just a sweet old lady. Many of her former friends/victims express shock and disappointment when they learn the truth.
In Kitsune no Ken: Fist of the Fox, Neji takes advantage of Kiba's despondency over Hinata's rejection of his (Kiba's) love confession and the revelation that Hinata had already had an Accidental Kiss with Naruto, to manipulate Kiba into fighting Naruto, as part of a plan to either get Naruto arrested (since Kiba's the son of Konoha Town's police chief) or expelled from school (Konoha High frowns on students with criminal records).
This could be the defining trope for Gaea from Noob. Cumulative info from media has her use Puppy Dog eyes and general charisma in the webseries and comic, the novels indicate that she tends to make speed psychological profiling of people she speaks with, is frequently scamming people and has to do a little of the lying thing to cover it all up. A few lines spoken by other characters in Season 5 however hint that after four years of her playing Horizon, "everyone knows that she's an opportunist".
Former ECW president and Smug Snake extraordinaire Paul Heyman fits this troop to a tee. He stole most of his ideas from other promoters like The Sheik, Joel Goodhart, and Atsushi Onita, and was not only able to convince his fans that they were his ideas, but that anyone else who used them was stealing from him. He was also able to convince them that they were watching only high quality wrestling, and that the WWF and WCW wrestlers were crap, while he made stars out of people like the Public Enemy and [911. Then there is the way he treated his wrestlers, which made them loyal to him despite the fact he had not paid them for the last six months. Even though most people that worked for him realize what a bastard he was in retrospect, he still has a strong Creator Worship following today despite his all his failures in the industry.
It was said of him in the DVD (Rise and Fall of ECW) that Paul always lied to the wrestlers, but he'd never lie to the fans.
WWE's commentators don't refer to Triple H as "The Cerebral Assassin" for nothing.
Raven, especially during his first ECW run and his WCW run, is another prime example just for his ability to gain loyal follower after loyal follower. The man got The Sandman's own wife and son to turn against him, for god's sake.
There's a good reason Edge is known as the "Master Manipulator".
Chaos in general in Warhammer 40,000 is very good at this, and the god Tzeentch in particular. The C'tan, who tricked the entire Necrontyr race into letting them eat their Life Force, deserve a mention too.
On the subject of Tzeentch, it is said that it has so many plans working in unison manipulating so many people and events that they effectively cancel each other out. Foiling one plan will cause a dozen more plans to initiate, which will in turn foil several dozen more plans... and so on and so forth.
Essentially, no matter what you do, you're furthering one or more plans of Tzeentch. I'm straining to remember the title, but one short story had a fairly prominent sorcerer engaged in a pitched battle: the forces of Chaos had far greater numbers and armaments, but the defenders were well dug in and supplied. The battle took months, and in the end a last-ditch effort on the part of the Imperials routed the remnants of his army and caused him to flee. The sorcerer feared for his life and soul, but on the first night had a vision from Tzeentch congratulating him on accomplishing just what he was supposed to do. When your greatest, most honored champions have no clue what your endgame is (or even if you have one) then you, sir, are beyond manipulative.
Part of the reason why Tzeentch is seldom the first guy who comes to mind in the 40k setting is that none of the writers either in fiction or rules really knows how to show Tzeentch succeeding. Almost all the fiction is from an Imperial viewpoint, which means they have to win, and so when Tzeentch crops up they tend to bust up one of his plans for reals, or at least genuinely setting him back because otherwise they may as well not have bothered. Tzeentch has never really gotten a chance to win or even be progressing and is always foiled by suitably clever and heroic imperials, which is somewhat contrary to his web of intrigue that has everything plotted out for every eventuality.
The real question is exactly what Tzeentch's designs might be. Out of all the Chaos gods he is the least Always Chaotic Evil and could be attempting to achieve... well ... anything in the long term. If anything, since conspiring in general is praise to Tzeentch, he could be slurping power out of all the bickering and politicking in the Imperium with eventual plan to re-introduce magic into their ranks, participating in wars and invasions to provoke further in-fighting in the Imperium. We just don't know, no-one has ever really tried to tell us, and that's why Tzeentch SHOULD be a manipulative bastard but tends to more feel like a very clever scooby-doo villain with no specific motivations that the bad guys can stop.
Tzeentch has plans, but he inherently has no agenda. Tzeentch, along with the other Chaos gods, is a psychic manifestation. He is the manifestation of plotting and change. He becomes more powerful simply by the existence of plots and change, not by them achieving any sort of actual objective. If Tzeentch ever definitively "won," he would cease to exist because there would be no one to plot against.
More recent editions have tried to justify Tzeentch's inscrutability by explaining that Tzeentch has no specific end goal, and rather his scheming is done purely for its own sake; in the cosmic scheme of things, Tzeentch is the ultimate pot-stirrer, with no specific ambitions beyond trying to cause whatever disruption in the Status Quo that he feels like. Individual minions may have their own end-goals, but Tzeentch himself simply does everything For the Lulz, and thus any confrontation against Tzeentch is inherently rigged in his favor; no matter what you do, whether you succeed or not, you've made something change, and through that you have served the God of Change.
Iago, from William Shakespeare's Othello, is the absolute definition of a Manipulative Bastard and the inspiration for many other entries on this list.
Shakespeare was using a traditional Christian theatre character called a Vice, who was always scheming and bragging to the audience. (Obviously it was a coveted role.)
If we're including Shakespearean Manipulative Bastards, then we also need to include Richard III.
In Shakespeare's King Lear, the appropriately-named villain Edmund The Bastard gets his brother disowned and banished by framing him for an attempt to kill their father Gloucester, then arranges for Gloucester to be disowned and banished after having his eyes gouged out; he does this all for political gains. After Edmund becomes Earl, he seduces two different women with promises of being queen, even though they are both sisters, and already married. He also secretly arranges for their father to be killed, and another sister as well, to solidify his claim to the throne.
The Black Knight in Middleton's A Game at Chess — a caricature of the Spanish ambassador Count Gondomar (who then had the play closed.) When told "Your plot's discovered", he exults "Which of the twenty thousand and nine hundred/Fourscore and five, can'st tell?"
Archie, who you would think would be 13's Morality Pet, is a more sympathetic version of this. He uses his Muscular Dystrophy to guilt people (mainly adults, as he is not one of the cool kids) to get what he wants. This is actually used as a Chekhov's Gun when he uses his disease to guilt Mrs. Goldman into buying tickets to an R-rated movie.
Madame Morrible in Wicked. The Wizard as well, but to a lesser degree, as he's too deluded and manipulated himself.
Hagen in DerRingDesNibelungen, who manipulates his siblings, Siegfried and Brunnhilda. This leads to Brunnhilda telling him how to kill Siegfried which will enable him to take the Ring of Power. By the end he loses the pretence, killing his brother Gunther to get the ring and trying to snatch the ring from the Rhinemaidens, getting him drowned.
Kirei Kotomine. He isn't even revealed as a bad guy despite his rather openly villainous attitude until late in each path, just as a jerk who likes messing with Shirou.
Even worse, Zouken Matou. He doesn't pretend to be a good/neutral guy or even bother masking the fact that he's a vicious and creepy old man.
Shizune of Katawa Shoujo. She's not the master manipulator Hisao thinks she is (probably...), but she is very cunning, her favorite game is Risk, and she has a lackey in Misha (well, a ditzy lackey with no volume control, but still.) Misha says late in Shizune's route that while she often manipulates people, some of those instances are unintentional.
Muv-Luv Alternative's Kouzuki Yuuko will do anything to ensure humanity's survival against the BETA. Anything. This includes surreptitiously releasing captured specimens on her own base to rattle the troops, not telling Takeru of the dire consequences of his going back to a branch of Extra, in general manipulating the members of the cast, the Americans, and the rest of the UN to ensure the success of Alternative IV. Even her Extra self is shocked at the depths to which she can stoop so low when the circumstances are present.
While Lear Dunham, the Big Bad of Broken Saints is the consummate Chessmaster, it is his Dragon / son, Gabriel, who is fits this trope better; he is easily able to earn Shandala's trust, play on Tui's jealousy like a drum, and keep the suspicious heroes calm long enough for the effects of his paralysis-inducing wine to kick in.
While not as extreme as some other examples, The Nostalgia Chick is pretty good at this. The best example is Kickassia, where she pretended to be sweet and nice to get her way, and then there's "Linking Up With Linkara" (along with MarzGurl) where they made Linkara think they had an epic, once-in-a-lifetime threesome.
In the novel Theatrica, Arthur proves to be an effective example of this trope.
Ladies and gentlemen, Survival of the Fittest's Aaron Hughes. This is a guy who, instead of killing an attacker, lets his ally get killed by said attacker, and goes back to his other allies portraying the poor victim as dying in a Heroic Sacrifice in an attempt to encourage them to get revenge on the murderer. Yikes.
Stephen Reyes from Shadow Unit. With knobs on. Just ask Chaz.
In Stupid Mario Brothers Season Four, Professor Oak willingly tricks Gary and Brock into doing several mundane tasks for him just so they could find out from him which one of them sucks more. Oak eventually claims they equally suck for not turning down the tasks. As a result the two fight over which one of them hates each other the most which Oak uses to his advantage once more.
Whateley Universe: in "Ayla and the Networks" it's pretty clear that everyone is trying to manipulate at least one other group, but the only one who really wins is Phase. Because he made his moves in previous stories, setting up everything.
Toki and she can get ANYONE to do her dirty work, oddly, as sort of a subversion, as they don't seem to mind and are aware of what she's doing. As per this description:
She's not fighting directly rather she's manipulating others to do it for her, in addition to playing dirty. It should be noted and can be properly assumed that she uses manipulation and deception to get what she wants and when she wants it. However, due to the obedience that her friends and the children of the house have that is to her and Doki especially, it is obvious on how she uses them to do her dirty work, nonetheless, don't seem to mind
Actually, Toki has standards and wouldn't go too far.
Giselle. During the first story of Giselle's Revenge, one would have to wonder how she would go, even if it meant harming a child.
Gaea from Noob makes good use of her Puppy-Dog Eyes to avoid contributing to her guild's fund, can do nasty blackmailing when she has the material for it and seems qui proeficient in the Con Man domain. Her plan involves accumulating all the in-game currency she can, apparenly by pure Greed, but Ivy assumes an undisclosed purpose in Season 5.