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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.
Dark Phoenix: Dark Phoenix | D'Bari (Vuk & Jones) | Brotherhood of Mutants (Magneto & Selene Gallio) | Mystique
The New Mutants: Essex Corp (Cecilia Reyes) | Demon Bear

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

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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
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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

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