Pennywise’s Dark Past Unveiled in Welcome to Derry Trailer
317A new trailer has dropped for HBO’s upcoming series “IT: Welcome to Derry,” and it promises a deeper look into the origins of Pennywise the clown. Bill Skarsgård is back as the terrifying Pennywise, and fans can expect several nods to Stephen King’s story, along with some creepy new details. The series is set to premiere in October, just a month away.
What’s New About the Derry Series?
This nine-episode prequel digs into the history of the small town of Derry, Maine, and the evil that haunts it every 27 years. It’s set in 1962, a period that fits perfectly with Pennywise’s cycle of terror. The show will explore events leading up to the original “IT” story, which focused on a group of kids called the Losers Club. These kids faced Pennywise’s deadly tricks and managed to stop him temporarily, only for him to return years later.
The series is planned to span three seasons, with each set in different years—1935 and 1908 being the next stops after 1962. This backwards storytelling approach is meant to reveal how Pennywise’s evil has persisted through the decades. Fans can expect to see how the town’s history ties into Pennywise’s endless cycle of horror.
Meet the New Characters and Connections
The trailer introduces new characters, including Taylour Paige as Charlotte Hanlon and Jovan Adepo as Leroy Hanlon, a Black couple who move to Derry with their son Will. Their arrival coincides with the disappearance of a local boy, which sets off a chain of terrible events. The series hints that the town’s dark secrets go beyond just Pennywise, touching on issues like racism and violence that have shaped Derry’s history.
Returning actors include Bill Skarsgård, who continues to bring Pennywise to life, and Chris Chalk as a young Dick Halloran. Halloran is a character fans will recognize from “The Shining” and “Doctor Sleep,” known for his psychic abilities. The cast also features Madeline Stowe, James Remar, and Rudy Mancuso.
In the trailer, viewers see a seemingly perfect town that hides some sinister truths. A girl named Lilly narrates, “Things happened here, but we don’t talk about it.” There’s also a quick shot of a bus from Shawshank prison, a fun nod to “The Shawshank Redemption.” The footage shows kids exploring dark sewers and a meteor crashing—clues that something ancient and powerful is awakening.
The clip ends with Pennywise’s menacing laugh and a glimpse of him holding his signature red balloon, signaling that the horror is just beginning. The show promises to be spooky and intense, filling in the gaps of Pennywise’s backstory and revealing what makes him so terrifying.
What to Expect When It Arrives
“IT: Welcome to Derry” looks like a chilling addition to Stephen King’s horror universe. It explores the origins of Pennywise and the dark history of Derry, with plenty of scares and mysteries. Fans of the books and movies will get a new perspective on the evil clown’s long-standing presence in the town.
The series will debut on October 26, 2025, on HBO and will be available to stream on HBO Max. With its mix of horror, history, and new characters, it’s shaping up to be a must-watch for horror fans and Stephen King enthusiasts alike. This prequel aims to set the stage for the horror that fans already know, while uncovering new secrets about Pennywise’s terrifying past.
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