Welcome to Derry Cast: Meet the Stars of the IT Prequel Series
Dive into the chilling origins of Derry, Maine. IT: Welcome to Derry, the highly anticipated prequel to the It films, has unveiled its star-studded ensemble. Reprising his iconic role, Bill Skarsgård returns as Pennywise, joined by a rich mixture of established talent and fresh faces. The series premiered on HBO on October 26, 2025, and unfolds across eight episodes.
A New Chapter in Horror Begins
IT: Welcome to Derry takes viewers back to 1962, years before the terrifying events of the original films. The series centers on the origins of Pennywise and the tumult of a town haunted by deep-seated fear. Bill Skarsgård returns as Pennywise, anchoring the story in known terror. His presence immediately signals that Derry remains as malevolent as ever.
Leading the Cast: New Faces and Key Players
The series is anchored by several compelling leads:
- Jovan Adepo portrays Leroy Hanlon, an Air Force major investigating the town’s darkest secrets.
- Taylour Paige stars as Charlotte Hanlon, Leroy’s wife and a community activist.
- Chris Chalk appears as Dick Hallorann, a psychic figure connecting It to Stephen King’s broader universe.
- James Remar plays General Shaw, a military figure with a deeper agenda.
This dynamic cast brings depth to a story that weaves together military intrigue, supernatural mystery, and social commentary.
The Children of Derry: A New Generation
A group of young actors bring the town’s youth to life, grappling with grief and fear:
- Clara Stack as Lilly Bainbridge, navigating loss and strange occurrences.
- Matilda Lawler as Marge, Lilly’s anxious friend.
- Amanda Christine portrays Ronnie Grogan, friend to Lilly and daughter to Stephen Rider’s character.
- Additional child actors include Blake Cameron James (Will Hanlon), Arian S. Cartaya (Rich), Miles Ekhardt (Matty Clements), Mikkal Karim‑Fidler (Teddy Uris), Jack Molloy Legault (Phil Malkin), and Matilda Legault (Susie Malkin).
Their evolving relationships become central to uncovering the eerie history looming over Derry.
Bringing the Community to Life
The series casts a wide net, drawing on a diverse ensemble to enrich Derry’s tapestry:
- Madeleine Stowe in a recurring role, adding gravitas.
- Rudy Mancuso as Captain Pauly Russo, a familiar face in the military narrative.
Further recurring roles include:
- Alixandra Fuchs, Kimberly Guerrero, Dorian Grey, Thomas Mitchell, BJ Harrison, Peter Outerbridge, Shane Marriott, Chad Rook, Joshua Odjick, and Morningstar Angeline.
These actors populate the world of Derry, adding nuance and depth to its haunting atmosphere.
Why the Cast Matters Now
IT: Welcome to Derry is more than a horror prequel—it’s a bridge between King’s universe and modern storytelling. Pennywise’s return anchors the series firmly within the familiar, while characters like Dick Hallorann deepen the connective tissue between King’s iconic tales. The ensemble’s diversity reflects Derry’s complexity—racial tensions, military influence, and generational trauma converge in the storyline.
Casting Timeline at a Glance
- April 2023: Taylour Paige, Jovan Adepo, Chris Chalk, and James Remar join the main cast, followed shortly by Stephen Rider and recurring casting of Madeleine Stowe.
- May 2024: Bill Skarsgård confirmed his return as Pennywise and takes on a producer role.
- June–July 2024: Multiple new recurring actors are added to expand the Derry community.
Filming began in May 2023 in Ontario and wrapped in August 2024, with production briefly halted due to the SAG-AFTRA strike.
What Viewers Are Watching For
- The Hanlon family, their investigation and emotional arcs.
- Pennywise’s presence—not omnipresent but haunting through tension and bursts of terror.
- Broader themes like systemic fear, societal prejudice, and Derry’s hidden past.
- The layered performances from both seasoned actors and emerging talents.
What’s Next
“Expect deeper exploration in future seasons, revealing more mysteries and stretching the boundaries of King’s universe.”
Season 2 is planned for 1935, followed by Season 3 set in 1908. The cast will evolve with the story, suggesting new characters and returning faces in different eras.
In Summary
IT: Welcome to Derry brings together a compelling cast for a story steeped in dread and history. Bill Skarsgård anchors the prequel as Pennywise, surrounded by veteran and emerging actors, including Jovan Adepo, Taylour Paige, Chris Chalk, Clara Stack, and more. Their performances help unravel Derry’s dark tapestry, making this series a must-watch for horror fans and King’s universe enthusiasts alike.
This cast doesn’t just haunt the sewers—they bring Derry’s secrets into terrifying clarity.
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