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Bill Skarsgård Returns As Pennywise the Clown In It: Welcome to Derry Trailer

Bill Skarsgård is back as Pennywise in HBO’s terrifying It: Welcome to Derry prequel series, and the first trailer promises more horror.

Jarrod SaundersbyJarrod Saunders
May 20, 2025
pennywise Bill Skarsgård Pennywise the Clown It Welcome to Derry Trailer

Image Credit: Fortress of Solitude

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There are four guarantees in life: death, taxes, reboots and creepy clowns hanging out in the sewers of Stephen King stories. And yes, he’s back. Bill Skarsgård returns as Pennywise the Dancing Clown in HBO’s It: Welcome to Derry, and the first trailer is here to ruin your sleep schedule this week.

After a Hollywood run that includes Eternals, Barbarian, John Wick: Chapter 4, Boy Kills World, The Crow, Nosferatu, and Locked, you’d think Skarsgård might take a break from playing disturbing characters. But here is back as the character who made him a household name. And we’re not complaining.

Set before the events of It (2017) and It Chapter Two (2019), the prequel series dives deeper into the cursed history of Derry, Maine—the creepiest fictional small town in America.

it-welcome-to-derry-trailer-hbo-max
Image Credit: HBO Max

The first It: Welcome to Derry trailer wastes no time setting the mood: a boy hitchhikes out of town, saying he wants to go “anywhere but Derry.” Wise kid. Someone should listen to him. But they won’t.

From there, the trailer introduces us to a Black family moving into Derry (this will probably end poorly for them), a group of teens unravelling the town’s spooky secrets, and, of course, Pennywise slinking around in a sewer, looking like he’s been waiting for this moment for years. Skarsgård’s return isn’t just a cameo; the man is in it—red balloons, sinister smiles and all.

“There’s something bad here in Derry,” a voice warns. Yeah, no kidding. Kids are going missing left and right, and yet, nobody seems to be calling the cops (or at least the cops don’t seem to care too much). It’s all very Derry. The adults are either oblivious, in denial, or maybe something worse. Just like in the films, it’s up to the kids to save the day. Or try to.

it-welcome-to-derry-trailer-hbo-max-black-family
Image Credit: HBO Max

Directed and executive produced by Andy Muschietti (who helmed both modern It films and The Flash movie), with Barbara Muschietti and Jason Fuchs also producing, It: Welcome to Derry is keeping it in the terrifying family. This series doesn’t feel like a throwaway cash grab—it looks like a full-on, serious expansion of the universe. And if you’ve been craving more of King’s lore beyond what the films gave us, this is it.

The show stars Taylour Paige, Jovan Adepo, Chris Chalk, James Remar, Stephen Rider, Madeleine Stowe, and Rudy Mancuso. It’s a talented cast that suggests HBO isn’t messing around.

The real star here is Pennywise, of course. Fans want to see more and know more about the mysterious evil clown.

The trailer for ‘IT: WELCOME TO DERRY’ has been released.

Premiering this fall on HBO. pic.twitter.com/40cUH5chos

— Film Updates (@FilmUpdates) May 20, 2025

RELATED: The It Cast: Where Are They Now?

The real question: Are you ready to go back to Derry? Or are you, like that smart hitchhiking kid, just trying to get the hell out? Either way, It: Welcome to Derry is waiting.

Tags: Bill Skarsgård Movies & TV ShowsHBOHorrorMovie Trailer
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About the Author: Jarrod Saunders

Jarrod Saunders is the Editor in Chief of Fortress of Solitude. An entertainment journalist and filmmaker with 18+ years of professional criticism. IMDb-credited director. Published by The Direct, Nicki Swift, and Thought Catalog. Watches 500+ films a year.

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