It: Welcome to Derry Episode 2 cast and characters - Meet the actors and guest stars of ‘The Thing in the Dark’

It: Welcome to Derry, the prequel series inspired by Stephen King’s legendary horror story, hit HBO on October 26, 2025.

By November 4, two episodes were out. The first episode dropped on October 26, and then Episode 2, called The Thing in the Dark, landed early on HBO Max for Halloween, with its official HBO premiere on November 2. The season has eight episodes in total.

It: Welcome to Derry Episode 2 really pulls you deeper into the creepy, unsettling world of Derry, Maine. It shines a light on both new faces and old, all of them tangled up in Pennywise’s chilling shadow. This episode digs into fear, paranoia, and trauma, showing how the town’s people start to crack as the supernatural threat closes in.

Here, we’re taking a closer look at the actors and guest stars who make Episode 2’s haunting characters feel real.

It: Welcome to Derry Episode 2 cast and characters

It: Welcome to Derry Episode 2 throws us right into the tangled lives of Derry’s residents. Every character brings their own baggage, and together, their stories make the town feel even darker, even more unsettling.

Jovan Adepo plays Major Leroy Hanlon. He is back from the military and can’t catch a break: he faces racism, fights his own inner battles, and tries to keep his family safe while Derry seems to close in on them. Leroy gets pulled into some wild supernatural and military secrets (“Operation Precept”).

Taylour Paige is Charlotte Hanlon, Leroy’s wife. Charlotte is sharp and deeply aware of the world around her. It: Welcome to Derry paints her as an activist, always tuned in to the tension in town and willing to speak up for what is right.

Blake Cameron James plays Will Hanlon, their son. He is the new kid and totally unprepared for the kind of trouble Derry has in store. Will’s innocence makes him an easy target for whatever is lurking in the shadows, but it is also what pulls him right into the heart of the mystery.

Chris Chalk takes on the role of Dick Hallorann in It: Welcome to Derry. Hallorann stands out as a community leader at Derry’s Air Force base, and he has this supernatural gift called “the shine.” He is in the middle of a top-secret mission tied up with all the strange things happening in town.

James Remar steps in as General Francis Shaw in It: Welcome to Derry. He has lived in Derry for years, and he runs the show at the Air Force base, especially during the height of the Cold War. Shaw is in charge of a top-secret mission called Operation Precept. The goal is to track down some kind of “weapon” to fight that strange, evil force haunting Derry.

Amanda Christine is Veronica “Ronnie” Grogan. Her dad runs the local movie theater, and she is the last person to see Matty Clements before he vanishes. Ronnie also faces a disturbing nightmare sequence (“The Mother Thing”), a surreal, terrifying vision tied to her mom and something way beyond the ordinary.

Clara Stack plays Lilly Bainbridge, a Derry High student who is struggling after her father’s death. She ends up at Juniper Hill Asylum, her grief and the way people push her aside land her there. In It: Welcome to Derry Episode 2, Lilly has an intense, terrifying vision in a grocery store. Out of nowhere, the pickle jars and a gruesome image of her father’s body hit her.

Jack Molloy Legault and Matilda Legault show up as Phil and Susie Malkin. They are kids living in Derry, Maine, back in 1962. Phil hangs out with Lilly and joins her group as they dig into the case of Matty Clements, a boy who has gone missing. Susie is part of their world, too, caught up in the same mystery.

Stephen Rider steps into the role of Hank Grogan in It: Welcome to Derry. Hank runs the local movie theater and raises his kid on his own. He gets tangled up in the story when people start pointing fingers at him for the kids going missing and turning up dead. On top of that, Hank deals with racial profiling and run-ins with the law, which brings some real-world grit and social commentary into all the creepy supernatural stuff happening in Derry.

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Even though the story centers on Pennywise the Dancing Clown, Bill Skarsgård’s unforgettable character, he is missing from the first two episodes. In the premiere, Pennywise doesn’t show up in that classic clown look; the creature slips in as other creepy, nightmare shapes instead. In episode two, there is a quick mention of those “Pennywise’s unmistakable eyes” glinting in the dark during a nightmare, but that is just a tease.

Other supporting and guest appearences in It: Welcome to Derry include: Madeleine Stowe, Rudy Mancuso, Alixandra Fuchs, Kimberly Norris Guerrero, Joshua Odjick, and Peter Outerbridge.

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