Settle in, readers—here’s the lowdown on “It: Welcome to Derry,” the highly anticipated It prequel that’s sending shivers down horror fans’ spines. HBO’s latest dive into Stephen King’s cursed Maine town, “Welcome to Derry” unveils a sprawling cast that threads together military tension, supernatural dread, and familial drama. Here’s who’s stepping into the shadows.
A Prequel Steeped in Mystery and History
“It: Welcome to Derry” is rooted in the dark origins of Pennywise and the chilling underbelly of Derry. The series begins in 1962 amid ominous disappearances and growing unease in the town. Recharge your memory: Bill Skarsgård returns as Pennywise. Alongside him, we meet a new cast of adults and children—many with connections to Derry’s deeper horrors.
The show premiered on HBO on October 26, 2025, introducing nine episodes that weave together military secrets and supernatural dread . The series is intended as the first of three, with future seasons reaching further back into Derry’s history—in 1935 and 1908 .
Principal Cast: Anchoring the Story
Jovan Adepo as Leroy Hanlon
Jovan Adepo plays Leroy Hanlon, an Air Force Major newly stationed in Derry. His arrival coincides with the town’s first unsettling disappearances—a catalyst for the unfolding horror . His presence ties into Derry’s racial and military history, grounding the supernatural in human conflict.
Taylour Paige as Charlotte Hanlon
Taylour Paige stars as Charlotte Hanlon, Leroy’s wife and Will’s mother. Paige brings emotional weight and strength to Charlotte, who navigates both motherhood and the creeping terror in their new town .
Bill Skarsgård as Pennywise / Bob Gray
Returning with equal parts menace and mystique, Bill Skarsgård reprises his iconic role as Pennywise, and also portrays the original human form, Bob Gray, in flashback sequences set in 1908 .
Returning Familiar Faces and New Additions
Chris Chalk as Dick Hallorann
Chris Chalk portrays a younger version of Dick Hallorann, the telepathic figure best remembered from The Shining. Set now in 1962 Derry, Hallorann serves in the Air Force and connects the series to broader King mythology .
James Remar as General Shaw
Veteran actor James Remar steps into the military chain of command as General Francis Shaw, a figure deeply enmeshed in Cold War-era agendas, possibly seeking a “weapon” with supernatural overtones .
Stephen Rider as Hank Grogan
Stephen Rider plays Hank Grogan, a projectionist at Derry’s local cinema and father to Ronnie. His performative humility and world-weariness make him a compelling link between the mundane and the uncanny. Notably, Rider once screen-tested to play adult Mike Hanlon in It: Chapter Two, making his casting here a poetic turn .
Rudy Mancuso as Captain Pauly Russo
Comedy star Rudy Mancuso plays Captain Pauly Russo, Leroy’s military buddy. His presence brings warmth amid the dread—and adds levity and camaraderie in tense moments .
Madeleine Stowe
Madeleine Stowe appears in a recurring role. While details are sparse, her attachment rounds out a cast blending Hollywood pedigree with rising talent .
The Children of Derry: Faces of Fright
Clara Stack as Lilly Bainbridge
Lilly Bainbridge, played by Clara Stack, is a central child character wrestling with grief, guilt, and supernatural encounters in Derry .
Amanda Christine as Ronnie Grogan
Ronnie Grogan, played by Amanda Christine, is Hank’s brave daughter. She forms part of the group of children caught in Derry’s dark undercurrent .
Arian S. Cartaya, Miles Ekhardt, Jack Molloy Legault, Matilda Lawler
The ensemble also includes Teddy Uris (Arian S. Cartaya), Matty Clements (Miles Ekhardt), Phil Malkin (Jack Molloy Legault), Susie Malkin (Matilda Legault), and Marge Truman (Matilda Lawler). These kids embody the early echoes of the Losers’ Club, forced to confront Derry’s terror .
Expanding Cast: Faces You Didn’t Expect
HBO added over ten recurring cast members to populate the haunted world of Derry. Notables include:
- Alixandra Fuchs
- Kimberly Guerrero
- Dorian Grey
- Thomas Mitchell
- Shane Marriott
- Peter Outerbridge
- Chad Rook
- Joshua Odjick
- BJ Harrison
- Morningstar Angeline
Their exact roles are undisclosed, but their inclusion enriches the tapestry of Derry’s residents, military personnel, and unseen victims .
On-Set Atmosphere: When Pennywise Walks In
Behind the scenes, the presence of Pennywise proved unnerving even for the cast. Young actors recount being intentionally shielded from seeing Skarsgård’s full costume to capture genuine fear on camera. One noted:
“We kind of got glimpses of him here and now and then… when we got to see him, it was so scary because he’s tall… plus the head… sometimes he had teeth and, like, blood.”
— Amanda Christine on seeing Pennywise during filming
Blake James (Will Hanlon) added:
“He’s six foot five, so you’re like, looking up at him. It’s terrible, I don’t wish that on anybody.”
This anecdote underscores how even seasoned performers were unsettled by Skarsgård’s transformation.
Summary Table: Who’s Who in Derry
| Actor | Character | Role in Story |
|---|---|---|
| Jovan Adepo | Leroy Hanlon | Air Force Major and new arrival |
| Taylour Paige | Charlotte Hanlon | Leroy’s wife, mother to Will |
| Bill Skarsgård | Pennywise / Bob Gray | The monstrous and human forms of the antagonist |
| Chris Chalk | Dick Hallorann | Military man with psychic tie-ins to The Shining |
| James Remar | General Shaw | Cold War–era commander overseeing dark projects |
| Stephen Rider | Hank Grogan | Projectionist and father figure |
| Rudy Mancuso | Captain Pauly Russo | Leroy’s Air Force confidant |
| Clara Stack | Lilly Bainbridge | Child struggling with grief and hidden danger |
| Amanda Christine | Ronnie Grogan | Brave daughter caught in Derry’s unfolding horrors |
| Arian S. Cartaya et al. | Teddy, Matty, Marge, etc. | Children forming early echoes of Losers’ Club |
| Supporting Ensemble | Various roles | Adds depth to military, town residents, and victims |
Why the Cast Matters Now
This cast reveal matters because it bridges King’s mythic horror with fresh, historically tinted storytelling. Military tensions, racial dynamics, childhood trauma, and cosmic malevolence collide in Derry. The series leans into a robust, morally complex ensemble to deliver textured suspense—starting with the Hanlons and stretching into the town’s shadows.
Their collective presence—terrified children, hardened servicemen, and the spectral clown—reinforces the idea that Derry’s horror is as much social and psychological as supernatural.
What’s Next for Derry
Looking ahead, Season 1’s journey through the 1962 timeline sets the stage for the deeper origin tales of Season 2 (1935) and Season 3 (1908). The rotating eras promise new casts, fresh traumas, and evolving strains of Derry’s curse .
Meanwhile, viewers can expect the remaining episodes of Season 1 to unspool new mysteries, character arcs, and the slow reveal of Pennywise’s place in Derry’s dark history. All eyes are on audience reactions and whether subsequent seasons get greenlit.
In short: “It: Welcome to Derry” introduces a rich ensemble of characters—from the Hanlon family to military figures, from terrified children to a chilling Pennywise. The cast’s layering of depth, fear, and narrative potential makes the series a must-watch for horror fans. Keep your eyes peeled—Derry’s secrets are just beginning to surface.
