The expansion of Stephen King’s most terrifying universe has arrived with the HBO original series IT: Welcome to Derry. Set in the early 1960s, this prequel serves as a chilling origin story for the town of Derry, Maine, and the malevolent entity that haunts it. Premiering on October 26, 2025, the series bridges the gap between the historical horrors of the town and the modern nightmares depicted in Andy Muschietti’s film duology.

The cast of IT: Welcome to Derry features a blend of returning horror royalty and fresh faces tasked with portraying the doomed residents of a town built on blood. From military officers at the local Air Force base to the ancestors of the Losers' Club, every character plays a pivotal role in the awakening of Pennywise the Dancing Clown.

The Return of Bill Skarsgård as Pennywise

The most significant casting news for the series is the return of Bill Skarsgård to the role of Pennywise (also known as It or Bob Gray). Skarsgård’s portrayal in the 2017 and 2019 films redefined the character for a new generation, moving away from the campier elements of the 1990 miniseries toward a more predatory, alien-like presence.

In IT: Welcome to Derry, Skarsgård also serves as an executive producer, ensuring that the creature’s lore remains consistent with the films. The prequel explores a version of Pennywise that is perhaps more primal, having recently awakened for its 27-year feeding cycle in 1962. Early footage suggests that Skarsgård is leaning into the shapeshifting nature of the entity even more heavily, appearing in various historical guises that hint at his long, dark history with the town’s founders.

The Hanlon Legacy: Taylour Paige and Jovan Adepo

At the emotional core of the 1960s narrative are the ancestors of Mike Hanlon, a key member of the Losers' Club.

Taylour Paige as Charlotte Hanlon

Taylour Paige takes on the role of Charlotte Hanlon. In the context of Derry's racial and social tensions of the 1960s, Charlotte is portrayed as an activist and a stabilizing force within her family. As the mother of Will Hanlon and grandmother to Mike, her character provides the historical weight needed to understand why the Hanlon family remained in Derry despite its inherent dangers.

Jovan Adepo as Leroy Hanlon

Jovan Adepo portrays Leroy Hanlon, a U.S. Air Force Major stationed at the Derry Air Force base. Adepo brings a sense of disciplined authority to the role, but as a Black officer in 1962 Maine, he faces external threats that are just as real as the supernatural ones. Leroy is the younger version of the character portrayed by Steven Williams in the 2017 film. His struggle to protect his family while serving a town that treats them with suspicion is a central theme of the season.

The Military Presence: James Remar and the Air Force Base

Unlike the films, which focused largely on the domestic and subterranean parts of Derry, the television series introduces a significant military subplot centered around the local Air Force base.

James Remar as General Francis Shaw

Veteran actor James Remar plays General Francis Shaw, Leroy Hanlon's superior officer. Shaw is a man of the Cold War era, obsessed with finding a "weapon" that could give the United States an edge over its enemies. His interest in the anomalous events surrounding Derry suggests that the military may have been aware of Pennywise’s existence—or at least the town’s high rate of disappearances—much earlier than previously thought.

Diesel La Torraca as Young Francis Shaw

The series utilizes a dual-timeline structure even within the prequel framework. Diesel La Torraca appears as a younger version of Francis Shaw in 1908, providing a direct link to the town’s earlier cycles of violence. This casting choice confirms that the show will explore the origins of the "Bob Gray" persona and the first times the entity interacted with the town’s social structures.

Connecting to The Shining: Chris Chalk as Dick Hallorann

One of the most exciting aspects of the IT: Welcome to Derry cast is the inclusion of Chris Chalk as Dick Hallorann. For fans of the "Kingverse," this character is a major bridge between IT and The Shining.

Hallorann is an Airman 1st Class with telepathic and clairvoyant skills—what he refers to as "the shining." In the novel IT, Hallorann is a cook at the Black Spot, a club for Black soldiers that was burned down by a racist hate group. Chalk’s performance captures the wisdom and underlying fear of a man who can sense the immense, ancient evil lurking beneath the sewers of Derry. His presence suggests that we will finally see the cinematic depiction of the Black Spot tragedy, a pivotal moment in Derry's dark history.

The Residents of Derry: Corruption and Innocence

Derry is famously a town that "ignores" the disappearance of its children. The cast representing the local townsfolk reflects this moral rot.

Peter Outerbridge as Clint Bowers

Peter Outerbridge plays Chief Clint Bowers, the corrupt head of the Derry police. As the ancestor of Henry Bowers (the bully from the films), Clint represents the generational cycle of violence and negligence. His character is instrumental in showing how the legal authorities in Derry were often complicit in covering up the entity's crimes, either through fear or direct influence.

Madeleine Stowe as Ingrid Kersh

Madeleine Stowe portrays Ingrid Kersh, the head housekeeper at Juniper Hill Asylum. Fans will recognize the name "Kersh" from IT Chapter Two, where an elderly woman claiming to be Pennywise’s daughter confronts adult Beverly Marsh. Stowe’s version of the character in the 1960s is deeply unsettling, serving as a human tether to the supernatural clown. Her relationship with "Bob Gray" (the human form Pennywise often takes) is one of the series' most disturbing mysteries.

The Young Misfits

The tradition of a group of children facing off against Pennywise continues here, though they are not the Losers' Club we know.

  • Clara Stack as Lillian "Lilly" Bainbridge: A young girl grappling with the recent death of her father.
  • Matilda Lawler as Marge Truman: A girl desperate to maintain her social standing in a town that is literally eating its young.
  • Blake Cameron James as Will Hanlon: Leroy and Charlotte’s son, whose curiosity about Derry’s history puts him directly in the clown's sights.

Supporting and Recurring Cast Members

The world-building in IT: Welcome to Derry is extensive, requiring a large supporting cast to populate the town’s 1962 setting.

  • Stephen Rider as Hank Grogan: The projectionist at the local cinema and father to Veronica "Ronnie" Grogan (played by Amanda Christine).
  • Rudy Mancuso as Captain Pauly Russo: Leroy Hanlon’s partner in the military, providing a lighter, more grounded foil to the surrounding horror.
  • Kimberly Norris Guerrero as Rose: A Native American woman who owns a pawn shop and possesses historical knowledge of the land Derry was built on.
  • Joshua Odjick as Taniel: Rose’s nephew, who becomes involved in the investigation into the missing children.

Why the 1960s Setting Matters for this Cast

The decision to set the series in 1962, rather than the 1950s (as in the book) or the 1980s (as in the first movie), allows the cast to explore a unique cultural intersection. This is the era of the Cuban Missile Crisis, the burgeoning Civil Rights Movement, and the transition from post-war optimism to the disillusionment of the late 60s.

The actors must navigate a Derry that is socially segregated and politically tense. The horror of Pennywise thrives on this division. For characters like Leroy Hanlon and Dick Hallorann, the threat is twofold: the supernatural monster in the sewers and the systemic racism of the town above. This adds a layer of "Experience" to the performances that goes beyond simple jump scares, grounding the horror in a recognizable reality.

Behind the Scenes: The Visionaries

The cast is supported by a creative team that knows this world intimately. Andy Muschietti, who directed the feature films, returns to direct four episodes of the series, including the pilot. His sister, Barbara Muschietti, serves as an executive producer.

The showrunners, Jason Fuchs and Brad Caleb Kane, have worked to expand the lore without contradicting the established films. Fuchs, who wrote the teleplay for the first episode, has mentioned in interviews that the goal was to treat Derry as a living, breathing character, and the casting choices reflect this ambition.

FAQ: Common Questions About the Welcome to Derry Cast

Is Bill Skarsgård really back as Pennywise?

Yes. After months of speculation, it was confirmed that Bill Skarsgård would reprise his role as Pennywise. He is also an executive producer on the project, ensuring the character’s continuity from the IT films.

Who is playing Mike Hanlon’s father?

Jovan Adepo plays Leroy Hanlon, who is the father of Will Hanlon and the grandfather of Mike Hanlon. The series explores the Hanlon family’s long history in Derry and their encounter with the entity during the 1960s.

Does Dick Hallorann appear in Welcome to Derry?

Yes, Chris Chalk plays a younger version of Dick Hallorann. This character originally appeared in Stephen King’s The Shining and was mentioned in the IT novel as the man who saved Will Hanlon during the Black Spot fire.

How many episodes are in the first season?

The first season of IT: Welcome to Derry consists of eight episodes, debuting on HBO and streaming on Max.

Are any other actors from the IT films returning?

While the series is a prequel set decades before the films, Joan Gregson reprises her role as an elderly Ingrid Kersh in a flash-forward sequence. Additionally, Sophia Lillis (Young Beverly Marsh) makes a guest appearance in a dream/vision sequence.

Summary of the Welcome to Derry Cast Dynamics

The cast of IT: Welcome to Derry is tasked with a difficult balance: honoring the legendary source material while creating a fresh narrative that stands on its own. By bringing back Bill Skarsgård, the series maintains a terrifying sense of familiarity. However, it is the new additions like Taylour Paige, Jovan Adepo, and Chris Chalk who provide the emotional and social context that makes the horror feel personal.

As we journey back to 1962, we see a Derry that is younger but no less haunted. The interplay between the military subplot and the local town residents creates a broader scope than the films, suggesting that the "It" entity is woven into every facet of the town's history. Whether you are a fan of the original novel or the recent films, this cast provides a compelling reason to return to the town where everyone floats.