Johan Liebert, the eponymous Monster. The title suits him
Dilandau Albatou from Vision of Escaflowne, although he was more psychotic than sociopathic
In the FMA manga and Brotherhood anime, Envy, Pride, Shou Tucker, and Kimblee are this as well. This version of Kimblee is a particularly chilling example of high-functioning sociopathy, being an extremely intelligent, extremely self-aware psychopath in the vein of Hannibal Lecter, masking his lunacy beneath a Faux Affably Evil facade and a bizarre code of honor.
Full Metal Panic!: Gauron is a Combat Sadomasochist and Death Seeker with a Hair-Trigger Temper, No Sense of Personal Space, No Social Skills, an utter Lack of Empathy, and an obsession with the hero that borders on the ephebophiliac.
Anton Chigurh from No Country for Old Men.
Roose Bolton from A Song of Ice and Fire is possibly one. Capable of extreme cruelty and betrayal, while never wavering from his Dissonant Serenity.
Alex from A Clockwork Orange (both the book and the movie).
Some interpretations of Sherlock Holmes. Another, probably much straighter example is Sherlock's Evil Counterpart Moriarty.
Though many of the supernatural creatures in The Dresden Files exhibit elements of sociopathy (notably vampires who fully embrace their predatory nature and many of the nastier Winter Court sidhe), the most obvious example is the all-too-human Nicodemus, a man so thoroughly and unapologetically (and yet often politely) evil that a Fallen Angel works with him as a genuine partner. Nick's wife Tessa and daughter Deirdre are also candidates.
The Silence of the Lambs: Dr. Hannibal Lecter, a Serial Killer and an Evil Genius, and perhaps one of the most famous examples of the inhumanly charismatic and exceptionally intelligent "elite psychopath" popularized by Ted Bundy and Jeffrey Dahmer.
Comedic Sociopathy
Ignatius Reilly from A Confederacy of Dunces has a Master's degree in history and believes life peaked with medieval feudalism and has degenerated ever since. He announces this loudly while bouncing between menial jobs and managing his valve.
Carl Hiaasen's novels usually include at least one unlikely, terrible, imaginative and painfully undignified death. A man dies during liposuction when the under-qualified surgeon (and bad guy) has a breakdown; another drowns after falling into a dolphin pool while the sexually-deviant dolphin has its way with him. What makes them hilarious is the bizarre circumstances and that it's the comeuppance of one of the book's villains.
Kitsu Chiri from Sayonara, Zetsubou-Sensei eventually got the role due to Characterization Marches On, and frequently snaps and murders (or is implied to murder) the extremely non-killable cast or attempts crazy stunts like splitting the Earth in half, taking over Sengoku-era Japan by killing everyone, or playing 'meat doll'. It gets so bad that when Chiri's attempt at 'surprising' the teacher ends up demolishing a wall and flattening all the desks in the classroom (and Ushio), everyone points out that this kind of behaviour is not very 'surprising' coming from her.
- Another example is (possibly) Kafuka, whose role as living in-universe Nightmare Fuel is mostly Played for Laughs.
The most impressive and villainous character in Ashita no Nadja? A 13-year-old girl. Yes, a teen Bitch in Sheep's Clothing and Nadja's Forgotten Childhood Friend: Rosemary. Said character steals the spotlight brilliantly by kicking puppies so well and hard that even the local Smug Snake, who thought the kid would be an easy-to-manipulate puppet at first, in the end utterly fears them. And for all that, the punishment amounts to nothing more than a slap in her face and willingly leaving the mansion. Karma Houdini, indeed.
Proxy One in Ergo Proxy, who is even referenced to be "the winner at the end of the world" (with good reason). Not only is he the master manipulator of nearly everything that happens in the course of the series, but he wins.
Johan Liebert - the Monster. He manipulates everyone he encounters as they were puppets on a string and then disposes of them without a second thought, subverts every Pet the Dog moment he's given in chilling ways, and never loses that Dissonant Serenity permanently affixed to his face. The problem is, the straight treatment the series gives his activities also makes him freaking scary to behold. A perfect example of a character who manages to be both this trope and a Complete Monster.
Miyo Takano from Higurashi No Naku Koro Ni certainly counts. She masterminded the events of the first six arcs, and loves frightening people with tales of Hinamizawa's past. Definitely a Magnificent Bitch. Also manages to be COMPLETELY EVIL (but mostly because of what the orphanage leader, Nomura, and Tokyo did to her).
Perhaps the most impressive and villainous character in Mon Colle Knights happens to be Redda, the Big Bad and final villain.
Though possibly more of a Guile Hero, Danny Ocean from Ocean's Eleven exemplifies the protagonist angle of this trope. A persuasive, imaginative, charismatic and highly organized professional criminal with an impeccable sense of style, Danny Ocean pulls off an impressive plan; robs the central vault of three casinos and gets his ex-wife to break off her relationship with the antagonist.
Graham Marshall (Michael Caine) in A Shock to the System. He methodically murders his bitchy wife and sleazy boss, beds his beautiful coworker, gets her to help him cover up the crimes after she finds out he did it (and drugged her to create an alibi), rubs the homicide cop's nose in it, and in the last scene takes out the chairman of the board and takes his place. And does it all with a Deadpan Snarker narration that is 200-proof Michael Caine gold.
Harry Lime from The Third Man. "Victims? Don't be melodramatic. Look down there. Tell me. Would you really feel any pity if one of those dots stopped moving forever? If I offered you twenty thousand pounds for every dot that stopped, would you really, old man, tell me to keep my money, or would you calculate how many dots you could afford to spare? Free of income tax, old man. Free of income tax—the only way you can save money nowadays." And he's played by Orson Welles.
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