Simon the Devious is a vampire that has a long-standing rivalry with Laszlo over a witch’s hat. He is played by the actor Nick Kroll.
Simon the Devious returns to hinder the lives of the Staten Island vampires in the latest episode of ‘What We Do in the Shadows’ but what exactly is his history with them?
Hopes of an alliance
In season 1 of What We Do in the shadows, Nandor, Laszlo, Nadja and Colin were tasked with taking over the new world by The Baron and to aid with their quest, they decide to visit Simon the Devious, the leader of the Manhattan vampires. Simon also leads a crew called the Leather Skins that do his bidding.
Laszlo and Nadja knew Simon from way back in the 1800s but they haven’t seen him in many years. They visit his club to make an alliance but Simon says that he will accept their proposal only if Laszlo gives him the witch skin hat that Laszlo owns. Laszlo adores the hat but Nadja is convinced that the hat is cursed.
Simon uses all the dirty tricks in the book and gets the hat from Laszlo before betraying them and kicking them out of his club. He tries to attack them with a flaming arrow but accidentally blows up his nightclub because of the cursed hat.
Laszlo retrieves the hat later on from Simon who is recovering in the hospital from his injuries.
Devious house guest
After the destruction of his nightclub, Simon the Devious falls upon hard times and begins living in the sewers while also losing the support of most of his crew. He shows up at the vampires’ doorstep and Nadja suggests letting him in and helping him get back on his feet.
Laszlo is still suspicious of Simon’s true motives and becomes paranoid. He falsely accuses him of trying to steal his hat when in reality, Simon was making a gift for the other housemates. Eventually, Simon ditches the facade and calls for a house meeting to decide who gets Laszlo’s witch skin hat.
He and Laszlo get into a fight that leads back into the sewers where Simon reveals that his crew is still with him and he has the upper hand. He talks about his craving for the hat grew out of jealousy watching Nadja and Laszlo have such a great relationship and that need is more important than leading his crew.
Simon then realises that his foot fused with a metal grate while he was transforming between bat and human form while wearing the hat. Laszlo takes the hat back and Simon is left to drown in the sewer as his crew abandons him for real after his harsh words.
The Staten Island vampires receive a visit from Bran and Toby Daltry, twin brothers with a reality show called Go Flip Yourself where they go to rundown house and renovate them.
Nadja accidentally kills Toby after which she hypnotizes Bran and the rest of the crew into carrying on with the show while thinking that Toby is sick.
Bran offers up several grand ideas on how to spruce up their mansion with one of them being to convert Laszlo and Nadja’s sleeping quarters into a walk-in closet for Him and Her where Laszlo can keep his hats.
When the time for the big reveal arrives, the vampires realize that there are barely any changes made to the house except for a few cosmetic ones. Bran takes them to the walk-in closet that has been completed and when Laszlo realizes that his witch skin hat is missing, Bran reveals himself to be Simon the Devious in disguise.
Simon says that he created an entire show and ran over 100 episodes just so that he could get into their house and steal the hat once more. He even reintroduces the Leather Skins who are masquerading as his crew. After saying his piece, Simon leaves but not before flying straight into the window sill because of the curse.
In a glimpse at the next episode of Go Flip Yourself, Simon is seen wearing the witch skin hat and show a couple the changes to their house but when he foes to switch on a gas stove, the house explodes leaving Simon’s fate up in the air.