It: Welcome to Derry: When does Pennywise appear in the latest horror prequel? Details revealed 

In It: Welcome to Derry, Pennywise doesn't appear directly, but flickers his darkness for the first time in episode 1 through poor Matty. When the kid is about to escape the town after he watches The Music Man in the movie theatre, he hitches a ride with a seemingly ordinary family. But soon things get more cryptic. The woman is shown pregnant and during the ride delivers a monster-like baby with 2 heads and a wing. The family's reaction to it adds to the eeriness.

Meanwhile, the neighbour kids start to look for Matty and run to the theatre where he was last seen. They play the reel of the film, and suddenly, on the screen, Matty appears, giving out a Pennywise-like smile. He is holding a baby wrapped in a cloth. He throws it towards the screen, and the same two-headed baby, now more enormous and dangerous, emerges from the screen to haunt the kids.

These are the scenes through which the show suggests the evilness of Pennywise, which has become even stronger this time. Read on to know more.

Here is when Pennywise appears in It: Welcome to Derry

As mentioned, when Matty was returning from the theatre hall, he hitches a ride with a seemingly ordinary family consisting of 2 kids, a pregnant mother, and the father. The sister is holding a bloody liver while the little brother seems to spell out absurd words. The mother starts to give him some dark words to spell. When the car moves to Derry, Matty realizes he is trapped.

The family starts to laugh and scream "O-U-T". The mother says that "It's coming out", and the baby inside the bump starts to move eerily. Matty tries to leave the car, but the mother goes into labour and finally delivers an absurd creature with wings and two heads. This is when we get the real hint of Pennywise's return, suggesting this family is his first victim.

Matty disappears after the event, and his classmates Teddy and Phil wonder where he could be. They haven't found the body yet, so Matty running away from Derry stands a fair chance. The kids then decide to go to the same movie theater for investigation, where Matty was last seen before disappearing in It: Welcome to Derry.

The overshadowing of Pennywise's evil does not end here in It: Welcome to Derry

Lily, another neighbour kid, is reeling from her father's gruesome accidental death. When she is alone in the bathroom, her peace turns to terror as she hears Matty's voice drifting up from the drain. His voice can be heard singing The Music Man number he had watched the night he vanished.

“We’ve got trouble,” he sings.

This scene in It: Welcome to Derry suggests that Matty has been a victim of Pennywise, the evil that travels through the sewage pipes. But of course, Lily didn't know he was hearing the voice of Matty, who is now Pennywise's latest victim. This also suggests how Matty is not alive in human form but is part of the evil force that lives beneath Derry. The overshadowing of Pennywise's evil does not end here.

When the kids, Lilly, Teddy, Ronnie, and Phil return to the theatre where Matty watched The Music Man. They play the reel of the film when the screen flickers and Matty appears. He looks at them with a Pennywise-like smile, holding a baby wrapped in cloth.

In a stunning, surreal moment in It: Welcome to Derry, the movie screen becomes a portal. The monstrous baby from the cold open bursts forth into the theatre, shattering the illusion of safety and dragging the kids and the viewers deeper into Derry’s nightmare.

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Episode 4 of season 2 is about to drop on November 16, 2025.

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