It: Welcome to Derry finally shows us a side of Pennywise that the films barely touched on. More frightening, more dangerous, the creature in the show is reshaped on a level that the version of him in the films look almost tame. This is Pennywise at his most terrifying, and the fifth episode really highlights this.
In the films, Pennywise cycles through an assortment of nightmare fuel. Yet even with all that absurd shape shifting, he never behaves the way he does in the show’s first minutes, when he appears as an entire family inside a car. That single scene introduces a Pennywise capable of slipping into groups of people at once, which immediately raises the stakes.
Episode five, titled 29 Neibolt Street, pushes that idea further. The episode begins with the kids finding Matty, the boy attacked weeks earlier, alive but weakened in their hidden clubhouse. He tells them he has been surviving underground and claims he knows where other missing children are being held. He also insists they avoid the police. That reaction should have looked suspicious, but relief blinds the kids. This is the first hope they have had in a long time, so they cling to it.
Once Matty leads them through the sewers toward the Neibolt House, the truth arrives like a shock. Pennywise reveals himself in Matty’s place, and the transformation is so violent that it leaves the kids scrambling. Episode five of It: Welcome to Derry makes the wait worthwhile by turning the reveal into a complete breakdown of everything the kids thought they understood about the creature.
How the fifth episode of It: Welcome to Derry changes how we see Pennywise
The most disturbing detail of It: Welcome to Derry's new episode is not the reveal itself but the implications. If Pennywise can imitate Matty for days at a time, and if he can wander above ground without anyone noticing, the limits placed on him before simply do not apply here. The episode suggests Pennywise can occupy multiple forms simultaneously. He appears as a prison guard when Hank is almost killed during a transfer to Shawshank. He appears as Matty on the same day. Later, he shows up as Charlotte, Matty, Pennywise, and Uncle Sam, all at once, deep in the sewers. Time and space do not restrict him.
Those descriptions also serve a purpose. Pennywise grows stronger when he terrifies children. Every horrific story he shares, every chilling detail he lets slip, feeds him. That is why he pushes so hard to keep the kids away from adults. Pennywise likely knows that his disguise will not work as easily on people who are older and more emotionally grounded. This could be the same reason the police could not see him in the photographs the kids developed. Adults may simply be too anchored to fall for the illusion.
Episode five proves that Pennywise in It: Welcome to Derry is far more dangerous than he has ever been portrayed. His reach is wider. His disguises are stronger. His cruelty is sharper. And the season makes it clear that the kids of Derry are facing something that refuses to follow the rules.
It: Welcome to Derry is now streaming on HBO Max.