Summary
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It: Welcome to Derry returns Bill Skarsgård as Pennywise, anchoring continuity from the 2017 and 2019 It films.
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New family leads Jovan Adepo and Taylour Paige take centre stage as the Hanlons, directly connected to the legacy of Mike Hanlon.
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The ensemble blends established actors (Chris Chalk, James Remar) with emerging names (Amanda Christine, Clara Stack) to deepen the cast’s reach into Derry’s horror-mythos.
The upcoming prequel series It: Welcome to Derry brings a fresh cast into the haunted town of Derry while re-establishing a direct link to the earlier films by returning Pennywise. Set in 1962, the story plunges into an earlier chapter of the curse, and the actors assembled reflect that generational inter-weave of fear and legacy. Here’s a guided tour of the key players and what they bring to the series.
Who returns and anchors the continuity of the cast in It: Welcome to Derry?
One of the biggest pieces of casting news is Bill Skarsgård reprising his role as Pennywise the Dancing Clown. His return ensures a direct connection to the films (It 2017 and It Chapter Two 2019) and provides a familiar anchor amid the new story setting. The series is set in 1962, making Pennywise’s presence earlier in the timeline significant. Bringing him back ensures that the cast isn’t just about fresh faces—it’s about maintaining continuity and satisfying fan expectations.
The presence of Skarsgård also signals the series won’t treat him as a peripheral figure. Reports highlight that Pennywise’s role is central. For the cast as a whole, this means the extremity of the villain’s presence raises the stakes for every actor involved.
READ MORE: IT: Welcome to Derry Release Date, Episode Schedule, and Global Streaming Guide
Which new family leads the prequel cast and how do they connect to the It legacy?
New leads Jovan Adepo and Taylour Paige headline the cast as Leroy and Charlotte Hanlon. Their family is positioned as the grandfather and grandmother of Mike Hanlon, tying this cast directly into the continuity of the original films rather than operating in an entirely separate universe. Adepo’s Leroy is portrayed as an Air Force Major relocating his family to Derry—bringing in themes of change, racial tension and familial adjustment. Paige’s Charlotte plays a schoolteacher whose classroom becomes entangled in the town’s supernatural horrors. The casting of these two anchors the series’ adult ensemble around a family that carries forward the legacy of the Losers’ Club era.
Complementing them is Blake Cameron James as Will Hanlon, their son. He provides the youthful tie to the main storyline and ensures that the cast has inter-generational reach. Together, these three create a family unit within the cast that serves as a fulcrum for the larger horror story. Their presence also allows the cast to explore not just terror, but relational dynamics: trust, protection, vulnerability.
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Which other adult and youth cast members round out the ensemble and what do they bring?
Beyond the Hanlons and Pennywise, the cast features several important additions. Chris Chalk plays Dick Hallorann, a crossover character from Stephen King’s The Shining universe, which broadens the cast’s reach into King’s multiverse. James Remar joins the adult cast as General Shaw, a Derry native with military authority—his presence adds dimension to the cast by introducing Cold War tension and institutional authority. Stephen Rider appears as Hank Grogan, a projectionist and single father to young Ronnie—this character adds grounded, human stakes to the cast list.
On the youth side, the cast features Amanda Christine as Ronnie Grogan and Clara Stack as Lilly, two young performers whose roles bring youthful vulnerability and discovery to the narrative. Mikkal Karim-Fidler as Teddy and Jack Molloy Legault as Phil round out the younger ensemble, giving the cast multiple vantage points on how children in Derry experience terror. The supporting cast is further strengthened by recurring talent: Madeleine Stowe appears in a mysterious capacity tied to Pennywise’s past, Rudy Mancuso appears as Captain Pauly Russo, among others. This layered cast ensures that the ensemble isn’t one note—its members span age, experience and narrative function, which enriches the overall cast architecture.
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The series It: Welcome to Derry is set to premiere on October 26, 2025 on HBO and HBO Max. It is the first season of what is planned to be a multi-season production, with this season set in 1962 and later seasons expected to explore 1935 and 1908.
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