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Cathal Gunning
Published 7 minutes ago
Cathal Gunning has been writing about movies, television, culture, and politics online and in print since 2017. He worked as a Senior Editor in Adbusters Media Foundation from 2018-2019 and wrote for WhatCulture in early 2020. He has been a Senior Features Writer for ScreenRant since 2020.
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Although Pennywise’s long-awaited appearance in It: Welcome to Derry is terrifying in its own right, it is particularly chilling when viewers think about the moment’s implications for the series as a whole. From It: Welcome to Derry’s opening scene, the prequel show made it clear that its version of Pennywise was even worse than the killer clown of the It movies.
Pennywise turns into all manner of monsters in the movies, including a witch-like elderly ghoul, a haunted painting, and a gigantic statue of Paul Bunyan. However, the entity doesn’t turn into a group of people, like it does when it takes the form of a family inside a car during It: Welcome to Derry’s opening scene.
Similarly, episode 5, “29 Neibolt Street,” made Pennywise’s powers even more disturbing. It was clear that something strange and supernatural was happening from the moment the show’s young heroes encountered Matty after Pennywise attacked him weeks ago, but the reality of their fate was one that completely rewrote the rules of how the monster works.
Pennywise’s Matty Disguise Makes It: Welcome to Derry’s Villain Much Worse
Bill Skarsgård's Pennywise with his monstrous mouth open in IT: Welcome to Derry episode 5
At the start of “29 Neibolt Street,” the kids find Matty alive, albeit worse for wear, in their secret clubhouse. He tells him that he has been surviving in the sewers and that he can take them to where the rest of the children are, but he refuses to talk to the police.
In fact, Matty says he’ll bolt if the kids try to involve any adult authorities, a comment that should have raised alarm bells for viewers. It is clear that something strange is going on with the survivor of the pilot’s first Pennywise attack, but the kids are so relieved to have Matty back and a lead that they don’t question this.
This turns out to be a mistake when Matty leads the group to the titular Neibolt House via the sewers and, in a truly terrifying sequence, transforms into Bill Skarsgard’s Pennywise. Although the monster has appeared in various forms throughout the last few episodes, including talking pickles and snail-like eye protrusions, this marks Pennywise’s screen debut.
While It: Welcome to Derry took a while to unveil its most iconic monster, “29 Neibolt Street” managed to make Pennywise even scarier in the process. Apparently, the entity can imitate people for days on end and walk around in the real world in broad daylight if it wants to, even appearing to multiple people at once.
Matty’s Return Hints At It: Welcome to Derry Episode 5’s Big Reveal
Throughout “29 Neibolt Street,” there are plenty of hints that something is seriously wrong with Matty. However, even though Pennywise taunted the kids at the theater in episode 1 by appearing as Matty inside a movie, it still seems unlikely that the child would be another form that the monster has taken.
The main reason for this is that Pennywise needs to be in numerous locations at the same time for the events of “29 Neibolt Street” to make sense. It possesses a prison guard when It: Welcome to Derry’s Hank is almost shot while being transferred to Shawshank, around the same time that it is appearing to the kids as Matty.
However, the episode’s ending makes it clear that this is no major feat for the monster, who appears as Charlotte, Matty, Pennywise, and Uncle Sam at the same time while down in the sewers. This allows the entity to terrorize multiple people around the same time, proving it isn’t limited by time and space.
It: Welcome to Derry even subtly hints at Matty’s true identity when he goes into a lot of unsettling detail, talking about how Pennywise killed the kids. When viewers find out Matty is actually Pennywise in disguise, it becomes clear that he is gloating by providing these detailed descriptions of his murders and relishing the fear it instills in his listeners.
Pennywise’s Confessions Could Explain His Powers In It: Welcome to Derry
While Pennywise takes a sadistic glee in revealing himself to the kids, like Marge’s attack in It: Welcome to Derry episode 4, his gruesome descriptions of his killings aren’t incidental. The more Pennywise scares the kids, the stronger he becomes, and the less likely they are to defeat him.
He’s indirectly strengthening himself by telling these stories, which might be why he tells the kids not to bring him to the cops when he’s disguised as Matty. Pennywise’s powers of disguise might not work against less susceptible, less impressionable adults, which could explain why the police could not see him in the photos that the children developed.
If the kids had brought Matty to the police station and the police had been unable to see him, this would have proven that he was just another one of Pennywise’s tricks, and they wouldn’t have followed him into the sewers. While It: Welcome to Derry’s Ingrid seemed suspicious until this episode, Pennywise’s human form was a more insidious one.
By taking the form of Matty, Pennywise fooled the kids and gave them hope for their dead friend, meaning they were all the more defeated and terrified when he revealed Matty was dead. This twisted plan proves just how dangerous It: Welcome to Derry’s villain truly is.
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It: Welcome to Derry
10 stars 9 stars 8 stars 7 stars 6 stars 5 stars 4 stars 3 stars 2 stars 1 star Like Follow Followed TV-MA Horror Mystery Drama Release Date October 26, 2025 Network HBO Directors Andy Muschietti Writers Jason Fuchs, Stephen King, Austin Guzman Franchise(s) IT
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Dick Hallorann with his eyes wide looking angry in It Welcome to Derry
Bill Skarsgard's Pennywise in IT Welcome to Derry trailer 2Image courtesy of HBO Max
Kid similing in IT Welcome To Derry
It: Welcome to Derry teens looking surprised at something off screen
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Do you think Pennywise's ability to imitate people for extended periods makes him a more terrifying villain compared to his previous iterations?
Cathal
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7 minutes ago
Some viewers might find this new power terrifying as it adds a layer of psychological horror, making it harder to trust anyone in the story. Others may prefer the more straightforward monster from the original. A few could argue that this change makes Pennywise too overpowered and less relatable.
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