12 Rounds: Miles Jackson is a suave, perpetually cheerful terrorist who masterminds the entire plot. Miles has evaded capture and conviction for his atrocities for years, always staying one step ahead of his law enforcement pursuers, and is introduced tricking a mole in his organization into betraying the F.B.I. and robbing them, after which Miles murders the same mole for ever thinking of turning on him. Though imprisoned for several years thanks to a freak accident, Miles breaks out of prison and sets up the game "12 Rounds" to be played with his arch enemy Danny Fisher. Using the excuse that he is getting revenge for his deceased girlfriend, Miles sets up various puzzles and traps throughout the city for Danny to figure out and stop, using the man's wife as a hostage the hold time. Miles' true magnificence comes with the reveal that the entire point of 12 Rounds was solely to serve as a long, complicated set-up to a bank robbery for millions of dollars, and that every round Danny played further assisted Miles in his scheme. Always ready with a quip and possessing a swaggering charisma that draws all eyes on him, Miles is an intelligent, charming villain, one capable of ridiculous amounts of manipulation and strategy, and whose very first scene illustrates his character perfectly by having him win a losing chess game for a stranger on a whim.
Catch Me If You Can: Frank Abagnale is a born Con Man whose first relatively harmless scheme involved impersonating his French teacher, fooling the entire school for weeks. His later criminal actions consist of acquiring millions of dollars by writing fraudulent checks, sending out fake letters, and posing as air plane pilots, doctors, and lawyers, all to live a lavish lifestyle spent in expensive hotels, throwing parties, and sleeping with numerous women he seduces, as well as a high-class prostitute whom he tricks into paying him for the night spent with her. When the FBI's Financial Crimes unit starts pursuing him, Frank cleverly manages to avoid capture numerous times, such as performing a Bavarian Fire Drill that convinces FBI Agent Carl Hanratty that Frank is a Secret Service agent, and in his most audacious scheme, smuggling himself through an airport filled with FBI agents by recruiting a group of handsome stewardesses to distract the men supposed to be watching out for him. Although the law ultimately catches up with him, Frank is a Lovable Rogue who is so good at what he does that he's able to elude the authorities for years and all before he was even 21.
Die Hard: These two show that magnificence runs in their family:
Die Hard: Hans Gruber is the mastermind behind the scheme to steal hundreds of millions in bearer bonds from the Nakatomi building. Meticulously orchestrating his operation, Hans shows his brilliance by constantly outmaneuvering the police and federal agents and his charisma by remaining level headed as his plan is disrupted and in his dealings negotiating with the hostages. To throw the cops off the trail of his robbery, Hans demands the release of the members of various terrorist groups, confusing the police force and hiding his true intentions. Confronted by the smug Ellis, Has tricks him into giving up McClane's name and nearly gets the location of the detonators McClane has taken. When caught unarmed by John McClane, Hans is instantly able to improvise with an American accent to pretend he is a hostage and throw off suspicion. Though utterly ruthless in the name of his avarice, Hans is an iconic villain because of his wit and charm, setting the stage for countless action villains to follow.
Die Hard with a Vengeance: Simon Gruber is a former soldier, Hans' older brother and master thief just like his sibling. Distracting the New York City police department with bomb threats, Simon strings along John McClane and Zeus to play games following his instructions lest he detonate his bombs. Pretending to be masterminding revenge for his brother, Simon mobilizes on his real goal: robbing the Federal Reserve for over one hundred billion dollars in gold bars, while the preoccupied police force leave it nearly completely unguarded for Simon and his men to plunder. When McClane attempts to follow his men, Simon improvises with a discarded bomb to flood the tunnel McClane is in, nearly drowning him. Alleging to destroy the gold to disrupt the American power-grasp on the world, Simon really means to make off with it himself. Every bit as adaptive and charming as Hans, Simon is yet another Gruber who shows to be a brilliant criminal.
Following: Cobb is ordered by a gangster (The Bald Guy) to kill one of his former lovers after she started blackmailing him, then notices that a stranger (the Writer) has been following him. He plays the Writer for a complete fool, implicating himself in the murder Cobb is planning under the guise of teaching him the art of burglary. He pretends to be working with the Blonde to implicate the Writer for another murder. He reveals he's working for the Bald Guy, kills the Blonde with the same weapon the Writer used earlier in another burglary, then disappears into thin air to let the Writer take the fall.
Fracture (2007): Theodore "Ted" Crawford hatches a plan that allows him to shoot his cheating wife, hide the murder weapon, confess to his crime, get himself acquitted and be immune against further prosecution, cause the suicide of the man sleeping with his wife, pull the plug on his comatose wife, and nearly get away with all of it. Crawford delights in playing mind games with the young hero Will Beachum, allowing Beachum to know he's guilty, but constantly dancing out of trouble via his own clever schemes until the end of the film. Despite being a murderer, Crawford manages to retain his charm and even a measure of sympathy, even handling his defeat with grace.
The Godfather: Part I: Vito Corleone, the Godfather himself, is the charismatic head of the Corleone family who started the crime family from nothing. After being bullied in his youth by the supposed mafioso Don Fanucci, Vito soon outplayed and disposed of him, becoming a "treasured friend" to the neighborhood who traded favor for favor. Even in his old age, Vito is the true strength of the Corleone family, who holds most of New York's judges and politicians in his pocket. When he is gunned down by the assassins of Virgil Sollozzo, Vito later returns after his eldest son's death, but uses a peace summit to determine who the true mastermind of the war was before making plans so his son Michael will wipe out all the enemies of the family, even after Vito's death. An iconic who defined The Don, Vito misses little chance to show why he is the most talented and powerful Don in the nation.
The Godfather: Part II: Hyman Roth, seeking revenge for his protege and friend Moe Greene at Michael's hands, has Michael's brother Fredo manipulated into giving his men a chance to murder Michael. Also manipulating a situation in New York through his proxies the Rosato Brothers, Roth has them attempt to murder Michael's New York caporegime, Frank Pentangelli, while making him think it was Michael's doing. Roth then uses Frank's survival to get him to turn witness for the State, even buying out the members of the Senate's investigative committee so Michael will be personally indicted. Soft spoken and relaxed, Roth hides an utterly devious mind, seeking personal revenge under the guise of everything being "strictly business" and comes closest to bringing Michael down.
Hard Candy: Hayley Stark is an extremely gifted teenage girl, who uses her intellect to lure out pedophiles, rapist and murderers. Hayley gets them into a false sense of security making them believe she is a naive young girl, before tearing into to them both physically and emotionally, then driving them to suicide. Upon luring out Jeff, Hayley tears into him so bad that she pushes him into the Five Stages of Grief, until finally calling his alleged former hookup, Janelle, and threatening to play the victim card in front of her unless Jeff kills himself.
James Bond: Of the many brilliant criminals and terrorists faced by the title character, these few manage to be even a cut about in suaveness and intelligence:
Dr. No: Dr. Julius No is one of SPECTRE's top operatives and a man of charm and charisma who rules Crab Key, Jamaiaca with his two metal fists. Seeking to disrupt a shuttle launch from America, No outplays everyone sent to the area until Bond's arrival, and even for much o the film Bond is entirely within No's power, only surviving thanks to outwitting No's assassins. When encountered by Bond, No reveals how he completely outwitted the Tongs after crawling up from nothing in Hong Kong as the son of a German missionary and a Chinese woman. Joining SPECTRE, No seeks to help overthrow the orders of east and west blocks alike, and remains one of the most dynamic and striking villains Bond ever faces.
The Man with the Golden Gun: Francisco Scaramanga was once a circus boy who loved an elephant. When the elephant was abused to death by its trainer, Scaramanga murdered the man and discovered a love for, and talent at killing. Becoming a master assassin, Scaramanga keeps his skills sharp by having his sidekick Nick Nack hire assassins to kill him so he can always test himself with his life on the line. Scaramanga also outplays the ostensible villain of the film, the industrialist Hai Fat, killing him to steal the powerful solar device to sell to the highest bidder and retire. When he has his hands on Bond, Scaramanga demonstrates his respect and wish to challenge Bond by challenging him to a duel, gleeful to show his own talents against the world's greatest secret agent.
Goldeneye: Once James Bond's best friend, Alec Trevelyan was the son of Cossacks who killed themselves after the betrayal of the British and Stalin's execution squads. Seeking revenge, Alec faked his death, betrayed the British and formed the Janus Crime syndicate. Alec proceeds to manipulate and organize several schemes to get his hands on the Goldeneye Satellite, even completely outwitting Bond and nearly killing him on several occasions, all while intending on robbing the British bank and then using the Goldeneye to erase the records, also nearly collapsing western civilization. One of Bond's most personal adversaries, Alec Trevelyan conducts himself with pure charisma, able to get under Bond's skin like no other by knowing him better than anyone else.
Skyfall: Once one of M's finest agents named Tiago Rodriguez, betrayed by her to the Chinese and tortured to the point of a bungled suicide that left him hideously disfigured, Raoul Silva escaped, joined SPECTRE under his new name and became a cyber-terrorist who plays the entirety of MI-6 perfectly. Using a series of terrorist attacks to lure out Bond, Silva proceeds to play mind games with him from their meetings, and allows his own capture so his encrypted laptop allows his men access to MI-6's systems. Escaping MI-6's custody, Silva hunts down M with the intention of achieving a mutual suicide with her, to end his pain with hers and secure his revenge against the woman he sees as a mother who betrayed him. One of Bond's most effective and brilliant adversaries, Silva even dies achieving almost everything he sets out to do, with M following him to death moments later.
Labyrinth: Jareth the Goblin King is a charismatic, manipulative goblin expertly played by David Bowie. First summoned by heroine Sarah, Jareth kidnaps her baby brother to lure her to him, spending the film manipulating the rest of the cast and tricking Sarah into eating an enchanted peach to make her more susceptible to his influence. Jareth shows a genuine care for Sarah, even if he is not above ruthlessly manipulating her and everyone else in the film, but never loses his sense of charm, flamboyance and friendliness, who even seems to care for the child he kidnaps upon her sister's rash wish.
Lucky Number Slevin: Slevin Kelevra was just a normal kid when both his parents were murdered on the orders of two mob bossess, The Boss and The Rabbi, to make an example of his father for trying to place a bet on a fixed horse race. The contract killer sent to take care of Slevin, Mr. Goodkat, couldn't bring himself to kill Slevin and instead raised him to follow in his footsteps as an assassin. Slevin spent years plotting the demise of his parents' killers with Goodkat's help, killing the Boss's son and both bosses' book keepers to make them even more paranoid of each other after they had already previously broken up their partnership. Goodkat then kills Nick Fisher so Slevin can pose as Nick's friend and be taken to the bosses to settle Nick's outstanding debts to both men. Slevin makes himself appear harmless before later killing the Rabbi's son as well and faking his own death, then kidnapping both mob bosses and suffocating them to death after explaining his reasons for wanting revenge. Slevin demonstrates that a dish Best Served Cold requires real mastery of the Kansas City Shuffle.
Captain America: Civil War: Helmut Zemo proves his stripes as one of the greatest manipulators of the franchise. Overcome with grief over losing his family during the Avengers battle with Ultron, Zemo decides to enact vengeance against them. Knowing he is no match for them in strength, Zemo instead devises an intricate plan to break them up. Launching an attack on a UN conference, Zemo frames Bucky Barnes for the attack which starts a manhunt against him. After Bucky is captured, Zemo impersonates a UN interrogator to activate Bucky's Trigger Phrase which will put him under his control to give him information on the death of Tony Stark's parents. Finally, Zemo leaks this ruse to the media, counting on Tony Stark following Cap and Bucky to the Hydra compound in Siberia so he can accomplish his real plan: show Tony evidence that Bucky killed his parents, causing him to fly into a murderous rage and attack Bucky and Captain America, permanently fracturing the Avengers in a way they may never fully recover from. By the end, in spite of being captured by T'Challa, Zemo still accomplishes what he wanted and gracefully accepts his capture and even offers to let T'Challa kill him to avenge the death of his father. Zemo stands out in a world full of super-powered beings, aliens, sorcerers and cosmic entities with only his intelligence and able to cement himself as one of the work's most successful villain, being the man who broke the Avengers.
Spiderman Homecoming: Adrian Toomes was once a hard working man who made a living salvaging Chitauri technology from The Incident. After having his occupation taken by Damage Control, he became a career criminal, taking the moniker The Vulture, and turning what was left of his salvaging company into an underground arms dealership, that would steal said technology and sell it to criminals. Toomes made sure not to leave any evidence for government officials to track his operations, while also making sure they aren't too big so that the Avengers won't view them as a threat; This process worked great for Toomes and his criminal business lasted for eight years without any problems. However, when he does face a problem in Spider-Man he isn't afraid to fight Spider-Man himself on several occasions; Spider-Man barely manages to survive those encounters with him. He is also able to uncover Spider-Man's civilian identity, Peter Parker, simply by analyzing Peter's behavior, and finds an opportunity to intimidate Peter from interfering with his operations. When this fails he sends The Shocker to distract Peter and later fights him for the final time so he wouldn't foil Toomes' latest heist job. Although threatening to kill Peter and his loved ones, its shown that Toomes greatly respects him, showing gratitude for saving his daughter's life, as well as his own, by not selling out his Secret Identity in prison, cementing Adrian Toomes as one of the most honorable, yet cunning foes in the films.
Minority Report: Lamar Burgess is the director and founder of the Precrime program, which uses premonitions extracted from three telepathic humans to predict and prevent all murder within the Washington D.C. area. However, at the same time Burgess is cunning enough to have literally made a career out of faking out Precrime; first by disguising Anne Lively's murder as an "echo", then by disguising all three visions of Crow's death as brown balls by putting the plan in action while Anderton was at the office, ensuring that he would either be arrested immediately or run, so when Crow would be found with the Orgy of Evidence that could lead Anderton to murder him, it looked planned by Anderton. When Federal Agent Danny Witwer catches on to him, Burgess promptly murders him, knowing that the system being deactivated will allow him to get away with it. The only thing Burgess couldn't see coming was Anderton figuring out everything in time to tell it all to his wife, even if he wasn't free to act on the information himself. However, even when his plot is exposed and faced with the impossible choice of either killing Anderton and going to prison or letting him live and discredit Precrime, Burgess manages to go out on his own terms by killing himself instead.
Saw: John Kramer aka the Jigsaw Killer was a law-abiding civil engineer before losing his unborn son, becoming estranged from his wife, and being diagnosed with terminal brain cancer in quick succession. Jigsaw uses his skills and intellect to become a prolific Serial Killer, designing elaborate death traps and picking his victims on the basis of their perceived lack of gratitude for the blessing of life. Fostering multiple protegés, only some of whom are even aware of each other, Jigsaw blackmails a hospital orderly to impersonate him to allay suspicion, manages to escape from police custody by manipulating the lead detective responsible for capturing him, uses his more devoted followers as back-up insurance against those who do not follow his teachings properly, and is responsible for schemes planned so far in advance that he continues to effect events even a decade after his death.
Unbreakable: Elijah Price, aka "Mr. Glass", was born with a genetic disease that causes his bones to be exceptionally brittle. After seeking solace in comic books handed him by his mother, he sets out to fulfill his life's purpose by becoming a supervillain and finding his heroic counterpart. He orchestrates several large-scale disasters such as train wrecks, hotel fires, and blowing up passenger planes, until he finally finds a miraculous Sole Survivor in David Dunn. Elijah proceeds to stalk David and his family, subtly manipulating him into fulfilling his destiny as a superhero until David answers his calling and saves several lives. Only then does Elijah knowingly expose his machinations to David, revealing David's new friend to in fact be his ultimate arch-nemesis, an Evil Genius who managed to kill hundreds while remaining undetected and was able to hide his true nature even from the hero.
Wild Things: Suzie Toller is a teenage girl from the wrong side of the tracks, masking her genius-level intellect by appearing as white trash. After one of her best friends was murdered by corrupt cop Ray Duquette, who then busted her on a bogus charge, Suzie vowed revenge. She hatches a plot wherein Suzie, her guidance counselor Sam Lombardo and Kelly Van Ryan, the rich girl Sam was sleeping with, are able to con Kelly's mother Sandra Van Ryan out of millions of dollars by having both girls falsely accuse Sam of rape, then cracking on the stand and opening the Van Ryans to a countersuit. Suzie also ordered Sam to draw Ray Duquette into the scheme by convincing him that he and Sam would get rid of both girls and split the money between the two of them instead of three-ways. After multiple betrayals and counter-betrayals and even faking her own death, at the end Suzie is the only conspirator left standing: a high-school drop-out responsible for several murders with a fortune safely stored away in an overseas account.
Wonder Woman (2017): The God of War, Ares once wiped out his fellow gods when they quarreled over Ares' wish to eliminate humanity. Surviving while injured and crippled, Ares instead plays on humanity's own preexisting prejudices and fears to sway them to destroy themselves, giving humans ideas for weapons and helping to manufacture peace that he knows they can't keep,setting the stage and giving them the matches to burn it down. When he reveals himself to Diana, Ares elaborates on his methods, also wishing Diana to join him to wipe out humanity and make the world a paradise.