Mr. Shadow

"How very touching. Here comes the brave prince to save the damsel in distress. Sorry, but the fairytale is over."

- Mr. Shadow taunting Taki after saving Makie.

Mr. Shadow is the main antagonist of the 1987 anime dark fantasy action film Wicked City.

He was voiced by Takeshi Aono in the original Japanese version, Jeff Winkless in the 1993 American English dub, and by Ray Lonnen in the British English dub.

Biography
Mr. Shadow is from the Black World, an alternate dimension comprised of demons that take humanoid shapes as disguises to enter the human world. A peace treaty between the worlds was maintained and compromised by the Black Guard, members from both the human world and the Black World. They are against a group of rogue Black Guard members from the Black World called the Radicals, who seek to destroy humanity for they see them as inferior to the demons of the Black World. Shadow was the leader of the terrorist group. He was romantically involved with another Radical named Makie, who soon turned against the Radicals and joined the Black Guard for she saw a need for peace between the two worlds.

When a salaryman and Black Agent named Renzaburō Taki is assigned to protect Giuseppe Mayart, a 200-year-old signatory for the treaty, Mr. Shadow sends his Radical henchmen to kill Taki, although he is saved by his assigned Black World partner, revealed to be Makie. As Mayart's plane arrives at the airport, the Radicals destroy it, killing everyone on board. But Mayart was already inside the airport, having boarded an earlier plane since he knew something like that would happen.

After a few more battles with Radical members and having to lose Makie within a barrier with a tentacle monster, Taki is introduced to Mr. Shadow through a small electric ball. Shadow reveals that he has Makie under his hands, visualizing a projection showing her being gang-raped by his men as punishment for betraying him. Shadow threatens to kill Makie once she has outlived her usage to him, taunting Taki to save her.

In the Radicals' hideout, Shadow has his temptress assistant hypnotize Taki into joining them, but Taki shoots her. Shadow orders his men to kill Taki, though Taki is able to defeat them. With only Shadow left, he managed to gain the upper hand against Taki by morphing the ooze from his fallen comrades against melted steel from the ceiling, forming hardened armor around himself, but Taki shoots where Shadow has left exposed, the inside of his mouth, causing him to explode.

However, that would not be the end of Shadow, as he has the ability to regenerate, even with only a chunk of his head left. He orders Kanako to go after the heroes, but Mayart reveals his true form as the guardian of his "bodyguards" and uses electricity to kill her. After Taki and Makie consummate in a church and Mayart reveals that the plan all along was to have a human and a demon produce a child to serve as the peace treaty between both worlds, Shadow appears again and attacks them.

Shadow at first gains the advantage by trapping Mayart within a dimension in his shadow and sends his fanged whip-like fingers in to rip him apart, although Taki shoots Shadow's other arm off, allowing Mayart to escape from the dimension by clinging on to Shadow's leg and shocks him with electricity. Shadow is then stapped through the head on a cross on the church's roof, destroyed when Mayart summons a massive lightning bolt. However, Shadow's arm regens a new Shadow. Suddenly, Makie reveals herself to have been impregnated by a human baby, granting her increased powers, allowing her to slice Shadow in half and blast him with light, killing him for good.