HBO’s It: Welcome to Derry unfolds in the 1960s, charting Pennywise’s malevolent influence upon the town before the events familiar from the blockbuster films. Bill Skarsgård returns to embody the dancing clown, joined by a ensemble exploring the Hanlon family lineage and military mysteries buried within Derry’s history.
The prequel series comprises eight episodes for its first season, directed and produced by Andy and Barbara Muschietti alongside Jason Fuchs. Executive producers include Skarsgård, Dan Lin and Roy Lee, with the narrative weaving together child disappearances, Air Force intrigue and Native American history.
Viewers first encountered the series when it premiered in October 2025, strategically positioned for the Halloween season according to cast interviews and engagement reports from that period.
Cast of It: Welcome to Derry Season 1
Bill Skarsgård reprises Pennywise / Bob Gray whilst serving as executive producer
Jovan Adepo and Taylour Paige portray Leroy and Charlotte Hanlon
2025 HBO/Max original series
Prequel to the It feature films
- Returning villain: Bill Skarsgård’s portrayal connects directly to his 2017 and 2019 film performances
- Military backdrop: Jovan Adepo stars as US Air Force Major Leroy Hanlon, husband to Taylour Paige’s activist Charlotte Hanlon
- Episode count: Season 1 consists of eight episodes
- Directorial vision: Andy and Barbara Muschietti helm the series, maintaining continuity with their film adaptations
- October 2025 premiere: The series debuted around Halloween with cast interviews confirmed for 27 October 2025
- Expanding mythology: Chris Chalk appears as Dick Hallorann, linking to The Shining universe through telepathic abilities
- Executive oversight: Skarsgård, Lin and Lee guide production alongside the Muschiettis and Fuchs
| Performer | Character | Role Description |
|---|---|---|
| Jovan Adepo | Leroy Hanlon | US Air Force Major, husband to Charlotte, father to Will (older iteration portrayed by Steven Williams in It (2017)) |
| Taylour Paige | Charlotte Hanlon | Activist and matriarch of the Hanlon family |
| Bill Skarsgård | Pennywise / Bob Gray | The ancient entity haunting Derry; also executive producer |
| Chris Chalk | Dick Hallorann | Airman possessing telepathic capabilities (previously depicted in The Shining and Doctor Sleep) |
| James Remar | Francis Shaw | Lieutenant General seeking a weapon; younger version portrayed by Diesel La Torraca |
| Madeleine Stowe | Ingrid Kersh / Periwinkle | Juniper Hill housekeeper and daughter to Bob Gray |
| Rudy Mancuso | Captain Pauly Russo | Recurring military figure |
| Alixandra Fuchs | Teresa “Terri” Bainbridge | Lilly’s absent mother |
IT: Welcome to Derry Kid Cast
The child ensemble anchors the horror elements, portraying youngsters confronting supernatural terror whilst navigating adolescence in 1960s Maine. Their performances illuminate the generational trauma that later characters inherit.
Leading Young Performers
Clara Stack embodies Lilly Bainbridge, a twelve-year-old grappling with paternal loss and maternal absence. Her friendship with Veronica “Ronnie” Grogan, portrayed by Amanda Christine, forms the emotional core of the youthful narrative. Blake Cameron James appears as Will Hanlon, the science-enthusiast son of Leroy and Charlotte who grows into the father of Mike Hanlon from the feature films.
Supporting Child Roles
Miles Ekhardt portrays Matty Clements, a child who disappears when Pennywise awakens. Mikkal Karim-Fidler and Jack Molloy Legault depict best friends Teddy Uris and Phil Malkin, whilst Matilda Legault plays Phil’s younger sister Susie. Arian Cartaya appears as Rich Santos, a Cuban American youth who befriends Will, with Matilda Lawler completing the principal children as Marge Truman.
Production records indicate most child performers were aged between nine and seventeen during late 2025 reporting, with several portraying characters younger than themselves—a standard practice in television productions requiring specific emotional maturity for horror narratives.
Welcome to Derry Release Date
Premiere Timing and Episode Structure
The series arrived on HBO and Max in October 2025, with scheduling deliberately coinciding with Halloween festivities. This timing mirrors the autumnal atmosphere central to Stephen King’s original mythology. Cast interviews conducted on 27 October 2025 featured principal performers including Jovan Adepo, Taylour Paige and the child ensemble.
Production Architecture
Season 1 comprises exactly eight episodes, blending military conspiracy with supernatural horror. Sources confirm the narrative incorporates Native American history alongside the child disappearance investigations that define Derry’s dark reputation.
Cast of IT: Welcome to Derry – Key Characters Like Lilly and Ronnie
Beyond the adult military personnel, specific child characters drive the plot’s emotional machinery. Their intricate backstories establish the psychological foundations for the town’s cyclical terror.
Lilly Bainbridge
Portrayed by Clara Stack, Lilly manages profound guilt whilst coping with her father’s death and her mother’s absence. Production notes indicate the character befriends Ronnie as a means of processing trauma, creating a bond tested by supernatural events.
Lilly’s narrative directly intertwines with Ronnie Grogan’s, establishing a friendship that mirrors the Losers’ Club dynamics seen in subsequent timelines, albeit within the distinct social context of 1960s America.
Ronnie Grogan
Amanda Christine brings Veronica “Ronnie” Grogan to life, the daughter of Hank whose alliance with Lilly provides crucial emotional support. Her character represents the working-class perspective within Derry’s stratified society.
Will Hanlon
Blake Cameron James depicts the twelve-year-old Will Hanlon, whose scientific curiosity and family background establish the lineage leading to Mike Hanlon. Character descriptions note his pivotal role in connecting the 1960s narrative to the later events of It (2017).
Young Will’s father Leroy and mother Charlotte’s experiences in 1960s Derry provide essential backstory for understanding Mike Hanlon’s deep connection to the town’s history in the feature films.
Production and Release Timeline
- Development Phase: HBO confirms the prequel series with Andy Muschietti attached to direct and produce alongside Barbara Muschietti and Jason Fuchs.
- Casting Announcements: Bill Skarsgård confirmed to return as Pennywise with Jovan Adepo and Taylour Paige joining as the Hanlon parents.
- Child Casting: Clara Stack, Amanda Christine and Blake Cameron James announced as principal young performers, with Rotten Tomatoes listings confirming ensemble details.
- Principal Photography: Production commences for the eight-episode first season, establishing 1960s period detail.
- October 2025 Premiere: Series debuts on HBO/Max, with Moviemeter records documenting the full cast roll-out concurrent with release.
Established Facts and Remaining Questions
Confirmed Information
- Eight-episode season structure
- October 2025 premiere window
- Complete adult and child cast rosters
- 1960s temporal setting
- Direct connection to It film universe
- Bill Skarsgård’s dual role as performer and executive producer
Uncertain Details
- Specific premiere date within October 2025
- Episode titles for all eight instalments
- Season 2 casting or production status
- Precise narrative connections to The Shining beyond Hallorann’s presence
- Viewing figures and audience metrics
Narrative Context and Universe Connections
Welcome to Derry functions as an origin story, excavating the events that established the cyclical pattern of violence defining the town. By focusing upon the Hanlon family—particularly Will’s parents—the series provides crucial context for Mike Hanlon’s resilience and knowledge in the feature films.
The inclusion of Dick Hallorann, familiar to audiences from The Shining and Doctor Sleep, suggests a broader Stephen King cinematic universe. Chris Chalk’s portrayal of the telepathic Airman during his military service creates intertextual resonance without requiring prior viewership of those films.
The 1960s setting allows exploration of mid-century American social dynamics, including military presence, racial tensions and small-town paranoia, all filtered through Pennywise’s predatory gaze. This temporal distance from the 1980s Losers’ Club narratives offers fresh perspective on the entity’s methodologies.
Sources and Production Statements
The series premiered around October 2025, aligning with Halloween, as indicated by cast interviews and viewer engagement reports from that period.
— Cast Interview Documentation, 27 October 2025
Season 1 comprises 8 episodes, blending military intrigue, Native American history, and child disappearances in Derry.
— Production Listings
Primary source material derives from official HBO announcements, verified cast listings on Wikipedia, Rotten Tomatoes cast databases, and entertainment journalism from Cosmopolitan and Netflix Junkie regarding specific performer details.
Summary
It: Welcome to Derry assembles a bifurated cast of established adult performers and emerging child actors to explore Derry’s haunted history. With Jovan Adepo and Taylour Paige anchoring the Hanlon family narrative and Bill Skarsgård returning as Pennywise, the eight-episode season bridges the mythology between the 1960s and the events depicted in the feature films. For comparison with the original Losers’ Club, see the Cast of It Chapter 1 – Complete Cast List and Key Roles.
Frequently Asked Questions
How many episodes comprise Season 1?
The first season contains eight episodes, combining military thriller elements with supernatural horror.
Who portrays Pennywise in the series?
Bill Skarsgård returns as Pennywise / Bob Gray, reprising his role from the 2017 and 2019 feature films whilst also serving as an executive producer.
Does the series connect to The Shining?
Chris Chalk appears as Dick Hallorann, establishing narrative continuity with The Shining and Doctor Sleep through the character’s earlier military service.
Who are the main child characters?
Lilly Bainbridge (Clara Stack), Ronnie Grogan (Amanda Christine) and Will Hanlon (Blake Cameron James) form the principal young ensemble.
When did the series premiere?
The series premiered in October 2025, with cast interviews confirming availability around the Halloween period.
Is there a Season 2?
No official confirmation regarding Season 2 casting or production has been established as of late 2025.
How does this relate to the IT films?
The series serves as a direct prequel to the films, exploring Pennywise’s 1960s influence and establishing the Hanlon family history that shapes Mike Hanlon’s character.
Where can viewers watch similar horror ensembles?
For comparisons with other supernatural horror casting, consult the Cast of The Conjuring Last Rites – Full Cast and Key Details.
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