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It takes more than bullets -- or a harlot's kiss -- to kill Nathaniel Essex.
~ Mister Sinister

Nathaniel Essex, or better known as Mister Sinister, is a major enemy for the X-Men, Cable and Deadpool and a powerful supervillain mutant who is bent on creating/becoming a being of genetic perfection and forcing the world's populace into the next step of evolution by weeding out those he believes are weak. He is the archenemy of Cyclops and one of the secondary antagonists of the X-Men as a whole.

Biography

During the 19th Century, Nathaniel Essex encountered Apocalypse who used his technology to transform Essex into "Sinister", the last word his dying wife ever spoke to him.

Soon after, a time displaced Gambit and Courier approached Sinister for help. Sinister agreed to help them, as long as he could have a DNA sample from Courier. This DNA sample allowed Sinister to replicate Courier shape shifting abilities, within Sinister’s own body.

By the early 20th Century, Sinister had cracked the genetic genome and was willing to share the information with Herbert Edgar Wyndham, who would later become the High Evolutionary.

During World War II, Sinister worked alongside the Nazis, collecting as many blood samples as he could. It was during this time that he first saw Sub-Mariner, and was inspired to create a clone of Namor. The clone was experiment N2 and had varied success against the original Namor but was defeated by Captain America.

Some time later, Sinister recruited Gambit to gather together the Marauders and ordered the massacre of the Morlocks. Sinister cloned Jean Grey in the form of Madelyne Pryor, so that Cyclops would have a child with her, which Sinister would view as the ultimate mutant. Ultimately, Cyclops rejected Pryor when Jean returned from stasis, and the youth would be carried to the future, where he would return to present era as Cable. Sinister's machinations would lead to the event known as Inferno, where Cyclops supposedly killed Sinister with an optic blast, although Sinister resurfaced alive and well, when he revealed that there was a third Summers brother.

Sinister was involved in Stryfe's attempted assassination of Xavier, trading Cyclops & Jean Grey to Stryfe in exchange for their DNA. However, Stryfe actually gave Sinister the Legacy Virus, which would terrorize mutant (and eventually human) life, and lead to the deaths of several mutants.

Sinister later involved himself with Nate Grey and the mutant Threnody. He joined the reestablished Weapon X program as Doctor Robert Windsor, claiming to help mutants escape Weapon X's mutant concentration camp "Neverland," but in reality, he took them to be his test subjects.

Other Appearances

X-Men Movies

Mister Sinister, or rather his true name Nathaniel Essex, is referenced in the post-credits scene of X-Men Apocalypse, where a group of mysterious men dressed in suits are shown entering the Weapon X facility at Alkali Lake and retrieving vials containing Wolverine's blood. The vials are placed in a briefcase bearing the name "Essex."

He was meant to appear in the post-credits scene of New Mutants, being portrayed by Jon Hamm, who also played Buddy in Baby Driver and Herb Overkill in Minions. He has since been removed from the film.

It is most likely that due to Essex Corp being under his name and that the organization has been behind certain events of X-Men: Apocalypse (Weapon X data), Deadpool 2 (Headmaster and Firefist) and New Mutants (Cecilia Reyes). Mister Sinister would have been the overarching villain of the New Timeline had the X-Men Cinematic Universe not ended with New Mutants.

Deadpool

In the 2013 video game Deadpool, Mister Sinister (or as Deadpool likes to call him, "Captain Douche") is the main antagonist, attempting to harvest mutant DNA from mutant corpses to become more powerful. His first move is hiring the corrupt media mogul Chance White, sending the Marauders to save him from Deadpool, who was trying to kill him and fulfill a contract. After Deadpool kills Arclight, the rest of the Marauders bring White to Sinister, revealing that White was setting up satellites for Sinister to control. Deeming Chance no longer useful, Sinister ordered Blockbuster to kill him. Angered over losing his money, Deadpool kills Vertigo with a gunshot and subdues Blockbuster with a kick before holding Sinister at gunpoint, demanding the money that the now-dead White owed him. The terrorist, however, easily defeated the Merc with a Mouth by using his telekinesis to violently dismember him, leaving Deadpool to regenerate unconscious.

Afterward, Sinister went to Genosha with the now-conscious Blockbuster in order to profane mutant corpses for their DNA, with Deadpool, the X-Men, and even Cable trying to stop him (Deadpool however, did not care about Sinister's plan and just wanted to kill him for revenge over his lost contract). In his way to find Sinister, Deadpool interfered in his plans, as he killed a clone of him which was broadcasting a signal through a security tower, rescued Rogue from Blockbuster, and stopped the profaning of corpses with Cable's help.

Wait, that was the real Sinister, right?
~ Deadpool after killing the real Sinister.

When Deadpool finally got to Mr. Sinister's base, Magneto's old citadel, the villain sent numerous clones, including that of the late Marauders, to fight him. After the Merc killed them all, the real Sinister finally showed up, angry with Deadpool's interference, quickly subduing the recently arrived X-Men using concussive blasts. Sinister started insulting Deadpool, without noticing he was standing right in a giant "X" the mercenary had painted before the final battle. Deadpool, commanding the player to "push the button", proceeded to punch Sinister in his crotch, and used a modified boot of a destroyed Sentinel to crush him when he was reeling from the pain, finally killing him. Initially confused if he was the real Sinister, Deadpool learned to his relief from Cable that he was indeed the real deal.

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Movies
X-Men: Brotherhood of Mutants (Magneto, Mystique, Sabretooth & Toad) | Pyro
X2: William Stryker Jr. | Lady Deathstrike | Jason Stryker | Brotherhood of Mutants (Magneto, Mystique & Pyro)
X-Men: The Last Stand: Brotherhood of Mutants (Magneto, Dark Phoenix, Pyro, Juggernaut, Multiple Man & Mystique) | Omega Gang (Callisto, Psylocke, Quill, Arclight, Avalanche, Spike, Glob Herman & Phat) | Archangel
X-Men: First Class: Hellfire Club (Sebastian Shaw, Emma Frost, Azazel, Angel Salvadore & Riptide) | William Stryker Sr. | Magneto | Mystique
X-Men: Days of Future Past: Trask Industries (Bolivar Trask, William Stryker Jr. & Sentinels) | Magneto | Mystique | Toad | Horsemen of Apocalypse (Apocalypse)
X-Men: Apocalypse: Ashir En Sabah Nur/Horsemen of Apocalypse (Apocalypse, Magneto, Psylocke & Archangel) | Dark Phoenix | Mystique | William Stryker Jr.
X-Men: Dark Phoenix: Dark Phoenix | D'Bari (Vuk & Jones) | Brotherhood of Mutants (Magneto & Selene Gallio) | Mystique
The New Mutants: Essex Corp (Cecilia Reyes) | Demon Bear | Reverend Craig | Smiley Men

Television
X-Men (1992): Magneto | Sentinels | Sabretooth | Juggernaut | Apocalypse | Mesmero | Horsemen of Apocalypse | Mister Sinister | Omega Red | Brotherhood of Mutants (Mystique, Avalanche, Blob & Pyro) | Dark Phoenix | Master Mold | Bolivar Trask | Silver Samurai | Hellfire Club (Sebastian Shaw, Harry Leland, Jason Wyngarde, Donald Pierce & Emma Frost) | Reavers (Bonebreaker & Lady Deathstrike) | Supreme Intelligence | D'Ken Neramani | Deathbird | Graydon Creed | Red Skull | Silver Samurai | High Evolutionary | Phalanx
X-Men: Evolution: Magneto | Brotherhood of Mutants (Mystique, Avalanche, Toad, Blob, Quicksilver & Scarlet Witch) | Pyro | Mastermind | HYDRA (Madame Viper & Omega Red) | David Haller | Juggernaut | Bolivar Trask | Sentinels | Apocalypse | Horsemen of Apocalypse | Mesmero | Destiny
Wolverine and the X-Men: Brotherhood of Mutants (Magneto, Mystique, Scarlet Witch, Juggernaut, Quicksilver, Avalanche, Blob, Pyro & Toad) | Dark Phoenix | Bolivar Trask | Sentinels | Sabretooth | Mutant Response Division (Colonel Moss) | Shadow King | Hellfire Club (Sebastian Shaw, Donald Pierce, Harry Leland, Selene Gallio, Emma Frost & Stepford Cuckoos) | Master Mold | Silver Samurai

           Wolverine-Logo-600x257.png Villains

Comics
Abomination | Absorbing Man | A.I.M. | Apocalypse | Arcade | Arnim Zola | Aryan | Baron Strucker | Bastion | Batroc | Beyonder | Bi-Beast | Blackheart | Blob | Bolivar Trask | Brotherhood of Mutants | Bushwacker | Cameron Hodge | Cassandra Nova | Collector | Crossbones | Crusader | Daken | Damage | Dark Beast | Dark X-Men | Deadpool | Deathwatch | Doctor Doom | Donald Pierce | Dracula | Egghead | Ego | Electro | Galactus | Green Goblin | Hand | HYDRA | Hobgoblin | Holocaust | Hulk | Impossible Man | Iron Monk | Juggernaut | Kingpin | Kraven the Hunter | Lady Deathstrike | Lady Mastermind | Lt. Ethan Warren | M.O.D.O.K. | Madame Masque | Madame Viper | Magneto | Master Mold | Masters of Evil | Master of Illusions | Mauvais | Mister Jip | Mojo | Morlocks | Mr. Sinister | Mysterio | Mystique | Nimrod | Nitro | Norman Osborn | Nuke | Omega Red | Onslaught | Prime Evil | Romulus | Reavers | Sabretooth | Savage Land Mutates | Sauron | Sebastian Shaw | Sentinels | Shadow King | Shingen Yashida | Silver Samurai | Spiral | Spot | Stryfe | Taskmaster | Tiger Shark | Titanium Man | Toad | Venom | Vermin | Vulture | Wendigo | White Rabbit | William Stryker | Winter Soldier | Wrecker

Movies
Hulk Vs. Wolverine: Professor Thorton | Deadpool | Lady Deathstrike | Sabretooth | Omega Red
X-Men Origins: Wolverine: William Stryker Jr. | Sabretooth | Deadpool | Agent Zero | Blob
The Wolverine: Silver Samurai | Madam Viper | Shingen Yashida | Noburo Mori | Magneto
Logan: Essex Corp (Zander Rice, Donald Pierce, X-24 & Reavers)

Television
Brotherhood of Mutants (Magneto, Mystique, Scarlet Witch, Juggernaut, Quicksilver, Avalanche, Blob, Pyro & Toad) | Dark Phoenix | Bolivar Trask | Sentinels | Sabretooth | Mutant Response Division (Colonel Moss) | Shadow King | Hellfire Club (Sebastian Shaw, Donald Pierce, Harry Leland, Selene Gallio, Emma Frost & Stepford Cuckoos) | Master Mold | Silver Samurai

Video Games
Black Cat | Brigade | Fault Zone | Hazmat | Johnny Ohm | Niles Van Roekel | Solara | The Wink | Vulture

           IMG 20190518 113114.jpg Villains

Comics
Absorbing Man | A.I.M. | Apocalypse | Arcade | Arnim Zola | Awesome Android | Batroc | Beyonder | Black Box | Black Talon | Brotherhood of Evil Mutants | Bullseye | Carnage | Chameleon | Constrictor | Crossbones | Dark Avengers | Deadpool | Dracula | Dreadpool | Doctor Bong | Doctor Doom | Doctor Octopus | Erik Killmonger | Fixer | Frightful Four | Grizzly | Hand | Hit-Monkey | Humbug | HYDRA | Hydro-Man | Juggernaut | Kingpin | Klaw | Lady Deathstrike | Loki Laufeyson | Mad Thinker | Magneto | Masters of Evil | Mephisto | Mister Negative | Mister Sinister | Mysterio | Norman Osborn | Piledriver | Punisher | Sauron | Sentinels | Skrulls | Stryfe | Swarm | Taskmaster | Thunderball | Thunderbolts | Tiger Shark | Titania | Tombstone | Trapster | Typhoid Mary | Ultimate Deadpool | Walrus | Wrecker | Wizard |

Movies
Deadpool: Deadpool | Dopinder | Ajax | Angel Dust | Agent Smith
Deadpool 2: Deadpool | Cable | Dopinder | Firefist | Juggernaut | Essex Corp (Headmaster) | Black Tom Cassidy | Sergei Valishnikov | Omega Red

           AC6C7A86-8942-4FFD-8947-EE4EEABBF47A.pngvengers Villains

Comics
Abomination | Abominatrix | Absorbing Man | Adolf Hitler | Agony | A.I.M. | Air-Walker | Alkhema | Aleksander Lukin | Alistair Smythe | Amatsu-Mikaboshi | Amora | Annihilus | Ani-Men | Answer | Apocalypse | Arcade | Ares | Arnim Zola | Atlas | Attuma | Avalanche | Awesome Android | Badoon | Barracuda | Baron Blood | Baron Mordo | Baron Wolfgang von Strucker | Baron Zemo | Baron Zemo II | Basilisk | Batroc | Beetle | Beyonder | Black Knight | Blackout | Black Order | Black Cat | Black Talon | Black Widow | Blackie Drago | Blastaar | Blitzkrieg | Blizzard | Blob | Blood Brothers | Bombshell | Boomerang | Brothers Grimm | Brotherhood of Evil Mutants | Bullseye | Burglar | Bushmaster | Bushwacker | Cache | Carnage | Carrion | Calypso | Celestials | Centurion | Chameleon | Chance | Chemistro | Chester Goudal | Chitauri | Collector | Colonel Ross Whittaker | Commander Kraken | Constrictor | Corruptor | Count Nefaria | Cowled Commander | Crime-Master | Crimson Dynamo | Crimson Widow | Cristu Bulat | Crossbones | Crossfire | Daken | Damage | Daniel Whitehall | Dark Avengers | Dark Elves | Deadpool | Deathbird | Deathurge | Death Adder | Deke Wainscroft | Demogoblin | Diablo | Doctor Doom | Doctor Faustus | Doctor Octopus | Doctor Spectrum | Dormammu | Dracula | Dreadknight | Eddie Brock | Eel | Egghead | Ego the Living Planet | Electro | Elementals | Elements of Doom | Enclave | Enforcers | Equinox | Exodus | Ezekiel Stane | Fabian Cortez | Famine | Fin Fang Foom | Finn Cooley | Firelord | Fixer | Fold | Frost | Frost Giants | Frightful Four | Galactus | Gargantus | Garthan Saal | Ghost | Goliath | Gladiator | Godzilla | Grand Director | Grandmaster | Grant Ward | Graviton | Green Goblin (Norman Osborn, Harry Osborn) | Grey Goblin | Griffin | Grim Reaper | Grizzly | Growing Man | Grotesk | Hammerhead | Hand | Hazmat | Hela | Hera | Herr Kleiser | Heinz Kruger | High Evolutionary | Hitman | Hive | Horsemen of Apocalypse | Hobgoblin | Hydro-Man | HYDRA | Immortus | Impossible Man | Ironclad | Jackal | Jack O' Lantern | Jester | Jigsaw | Johnny Ohm | Jonas Hambleton | Jormungandr | Juggernaut | Justin Hammer | Kaine | Kang the Conqueror | Killer Shrike | King Cobra | Kingpin | Klaw | Knull | Korath the Pursuer | Korvac | Kraven the Hunter | Kree | Lady Deathstrike | The Leader | Lightmaster | Living Brain | Living Laser | Living Monolith | Lizard | Loki Laufeyson | Lucia Von Bardas | Ma Gnucci | Machinesmith | Mad Pharaoh | Madame Masque | Madame Viper | Madcap | Madelyne Pryor | Maelstrom | Maestro | Maginty | Magneto | Magus | Malekith the Accursed | Man-Ape | Mandarin | Mandrill | Man-Spider | Man-Wolf | Master Man | Master Pandemonium | Masters of Evil | Masked Marauder | Maximus the Mad | Melter | Menace | Mentallo | Mercurio the 4-D Man | Mesmero | Mephisto | Mister Fear | Mister Hyde | Mister Negative | Mister Payback | Mister Sinister | M.O.D.A.M. | M.O.D.O.K. | Mojo | Molecule Man | Mole Man | Molten Man | Moonstone | Morbius the Living Vampire | Morgan le Fay | Moses Magnum | Mystique | Mysterio | Namor | Nebula | Nekra | Nicky Cavella | Nightmare | Nightshade | Niles Van Roekel | Nicky Cavella | Obadiah Stane | Omega Red | Onslaught | Overdrive | Owl | Paladin | Phalanx | Phil Urich | Piledriver | Pluto | Presence | Princess Python | Proctor | Psycho-Man | Puppet Master | Puma | Purple Man | Quasimodo | Quicksand | Radioactive Man | Ragnarok | Ramrod | Reavers | Red Ghost | Red Skull | Reverend Samuel Smith | Rhino | Rhino II | The Rose | Ringer | Ringmaster | Riot | Ronan the Accuser | Roxxon | Sabretooth | Sandman | Säurespritze | Sauron | Savage Land Mutates | Scarecrow | Scarlet Witch | Scorcher | Scorpion | Screaming Mimi | Sebastian Shaw | Secret Empire | Selene Gallio | Sentinels | Sentry 459 | Serpent Society | Shriek | Shocker | Shockwave | Sidewinder | Silver Sable | Sin | Sinister Six | Skaar | Skeleton Crew | Skrulls | Skurge | Slug | Space Phantom | Spider-Man Revenge Squad | Spider-Slayers | Spot | Squadron Sinister | Stranger | Street | Sunstroke | Superia | Super-Adaptoid | Super-Apes | Super Patriot | Super-Skrull | Supreme Intelligence | Superia | Surtur | Swarm | Swordsman | Symbiotes | Tarantula | Taskmaster | Technovore | Temugin | Ten Rings | Terminus | Thanos | Thunderball | Thunderbolts | Thunderbolt Ross | Thundersword | Tiger Shark | Tinkerer | Titania | Titanium Man | Toad | Tombstone | Trapster | Trick Shot | Terrax the Tamer | Typhoid Mary | Tyrannus | U-Foes | Ulik | Ultimus | Ultron | Unicorn | Universal Church of Truth | Vapor | Vector | Venom | Vermin | Vulture | Walrus | Warlord Krang | Whiplash | Whirlwind | White Rabbit | Will-O'-The-Wisp | Winter Soldier | Wizard | Wonder Man | Wrecker | Worthy | X-Ray | Yellow Claw | Ymir | Yon-Rogg | Zahnmörder | Zodiac | Zzzax

Television
The Avengers: United They Stand: Ultron | Kang the Conqueror | Swordsman | Ringmaster | Masters of Evil (Baron Zemo, & Whirlwind) | Attuma | Zodiac (Taurus & Scorpio) | Egghead | Scarlet Witch | Grim Reaper
The Super Hero Squad Show: Doctor Doom | Mole Man | Fin Fang Foom | Abomination | Wrecker | Thunderball | Piledriver | M.O.D.O.K. | Klaw | Toad | Melter | Dormammu | Sabretooth | Juggernaut | Pyro | Whirlwind | Zzzax | Enchantress | Baron Mordo | Punisher | Egghead | Ringmaster | Skrulls (Super-Skrull) | Trapster | Mystique | Impossible Man | The Leader | Mad Thinker | Skurge | Crimson Dynamo | Batroc the Leaper | Loki Laufeyson | Magneto | Quicksilver | Scarlet Witch | HYDRA (Red Skull , Arnim Zola & Baron Wolfgang von Strucker) | Galactus | Terrax the Tamer | Firelord | Stardust | Thanos | Kree | Ego the Living Planet | Grandmaster | Annihilus | Nebula | Ronan the Accuser | Nightmare | Ultron | Dark Surfer | Sentinels | Dracula | High Evolutionary
Avengers: Earth's Mightiest Heroes: HYDRA (Red Skull, Baron Von Strucker, Grim Reaper, Arnim Zola, Doughboy & Madame Viper) | Masters of Evil (Baron Zemo, Enchantress, Skurge, Chemistro, Abomination, Crimson Dynamo & Grey Gargoyle) | A.I.M. (M.O.D.O.K.) | Kree Empire (Supreme Intelligence, Colonel Yon-Rogg & Ronan the Accuser) | Absorbing Man | Klaw | Ultron | Wrecker | Thunderball | Piledriver | Red Hulk | Frost Giants (Loki Laufeyson & Ymir) | Technovore | Bi-Beast | The Leader | Whirlwind | Kang the Conqueror | Man-Ape | Malice | Mad Thinker | Mandrill | Graviton | Fenris Wolf | Lucia Von Bardas | Zzzax | Blizzard | Constrictor | Griffin | Living Laser | Whiplash | King Cobra | Magneto | Wendigo | Skrulls (Super-Skrull) | Malekith the Accursed | Hela | Doctor Doom | Surtur | Glenn Talbot | Winter Soldier | J. Jonah Jameson | Destroyer | Annihilus | Purple Man | Galactus | Firelord | Stardust | Terrax the Tamer
Avengers Assemble: HYDRA/A.I.M. (Red Skull, M.O.D.O.K., Blood Brothers, Grim Reaper, Crossbones & Baron Wolfgang von Strucker) | J. Jonah Jameson | Doctor Doom | Ulik | Impossible Man | Dracula | Hyperion | Wrecker | Thunderball | Piledriver | Destroyer | Loki Laufeyson | Chitauri | Justin Hammer | Mojo | Galactus | Ringmaster | Black Order (Thanos) | Hela | Winter Soldier | Nighthawk | Dormammu | Ultron | Roxxon Energy Corporation | Absorbing Man | Titania | Whirlwind | Fin Fang Foom | Masters of Evil (Baron Zemo, Beetle & Goliath) | Klaw | Ghost | A.I.M. (Kang the Conqueror, Whiplash & Spymaster) | Abomination | Kree Empire | Egghead | The Leader | Crimson Widow | Arnim Zola | Enchantress | Skurge | Typhoid Mary | Ares | Taskmaster | Doughboy | Ulik | Beyonder | Symbiotes | Morgan le Fey | Tiger Shark | Erik Killmonger | Man-Ape | Madame Masque | Kraven the Hunter | Vulture

Movies
Ultimate Avengers 1 & 2: Herr Kleiser | Chitauri
Next Avengers: Heroes of Tomorrow: Ultron
The Avengers: Loki Laufeyson | Chitauri (The Other & Leviathans) | HYDRA (Gideon Malick & Jasper Sitwell) | Georgi Luchkov | Thanos
Avengers: Age of Ultron: Ultron | Ultron Sentinels | HYDRA (Wolfgang von Strucker, List, Scarlet Witch & Quicksilver) | Ulysses Klaue | Madame B | Chitauri (Leviathans) | Thanos
Avengers: Infinity War: Black Order (Thanos, Ebony Maw, Proxima Midnight, Corvus Glaive, Cull Obsidian, Nebula, Outriders, Chitauri & Leviathans) | Red Skull | The Collector | Loki Laufeyson | Winter Soldier | M'Baku | Scarlet Witch | Thunderbolt Ross
Avengers: Endgame: Black Order (Thanos, Ebony Maw, Proxima Midnight, Corvus Glaive, Cull Obsidian, Nebula, Outriders, Sakaaran Mercenaries, Chitauri, Leviathans & Chitauri Gorillas) | HYDRA/STRIKE (Red Skull, Alexander Pierce, Crossbones, Jasper Sitwell & Jack Rollins) | Loki Laufeyson | Winter Soldier | M'Baku | Scarlet Witch | Kraglin Obfonteri | Dark Elves | Thunderbolt Ross | Akihiko

Video Games
Marvel's Avengers: M.O.D.O.K. | Monica Rappaccinni | Abomination | Taskmaster | Super-Adaptoid | Lyle Getz

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