Cast of IT: Welcome to Derry: Actors, Characters & More

Fans of the IT franchise finally got the prequel series they’ve been waiting for. HBO’s IT: Welcome to Derry brings back Bill Skarsgård as the menacing Pennywise the Dancing Clown, this time alongside a fresh ensemble of adult and kid actors portraying Derry’s inhabitants across multiple eras. The show bridges the original films with new stories that explore how the town became the horror it is.

Pennywise: Bill Skarsgård · Charlotte Hanlon: Taylour Paige · Leroy Hanlon: Jovan Adepo · Premiere Year: 2025 · Season 2 Status: In development

The HBO production rounds up the core cast assignments for the prequel series.

Who will be playing Pennywise in Welcome to Derry?

Bill Skarsgård officially returns as the terrifying Pennywise the Dancing Clown in IT: Welcome to Derry. According to Wikipedia production details, Skarsgård was cast in May 2024 and also serves as an executive producer on the series. His portrayal of the shapeshifting entity first debuted in the 2017 IT film and continued in the 2019 sequel, establishing one of horror cinema’s most iconic villains.

Bill Skarsgård’s return as Pennywise

Skarsgård’s commitment to the role spans the entire production timeline. Media sources describe him as a creature actor who has built a reputation for physically demanding monster roles (Wikipedia actor profile). In IT: Welcome to Derry, he reportedly appears across multiple time periods, anchoring the supernatural thread that connects Derry’s dark history.

Origin of Bob Gray as Pennywise

The series delves deeper into the mythology of Pennywise by exploring how the entity known as Bob Gray became the clown that haunts Derry’s children. Production notes indicate the prequel format allows the show to examine the character’s origins more thoroughly than the original films could.

Who is the new cast of Welcome to Derry?

Beyond Skarsgård, HBO assembled a strong adult ensemble led by Taylour Paige and Jovan Adepo. The initial cast announcements in April 2023 revealed the core performers (Wikipedia), with subsequent additions filling out supporting roles.

Main adult cast members

• Taylour Paige portrays Charlotte Hanlon, an activist, wife of Leroy, and mother of Will. Her casting as the lead female character brings gravitas to the series.
• Jovan Adepo plays Leroy Hanlon, a US Air Force Major and father of Will. An older version of this character appeared in the 2017 IT film, played by Steven Williams.
• James Remar takes on Francis Shaw, a US Air Force Lieutenant General searching for a Cold War-ending weapon. A young Francis Shaw in 1908 is played by Diesel La Torraca.
• Stephen Rider joined as a series regular playing Hank Grogan, announced around April 2023 (Brit + Co entertainment coverage).
• Chris Chalk portrays Dick Hallorann, continuing connections to the wider IT universe (Brit + Co).
• Madeleine Stowe appears as a recurring guest as Ingrid Kersh / Periwinkle, with younger versions played by Tyner Rushing and Emma-Leigh Cullum in earlier time periods (Wikipedia).

Supporting roles like Hank Grogan

Additional supporting cast includes Peter Outerbridge as Chief Clint Bowers and Kimberly Guerrero as Rose, according to TV Guide cast listing. The series creator Andy Muschietti, along with Barbara Muschietti and Jason Fuchs, shapes the production vision that brings these characters to life.

Which characters from Welcome to Derry are in it?

The series features an extensive roster spanning multiple eras of Derry’s history. From young children in the 1930s and 1960s to adults navigating the town’s supernatural threats, the character ensemble draws from Stephen King’s source material while introducing new faces.

Key characters and actors

• Matilda Lawler plays Marge (or Marge Truman), a character central to the kid storyline (Brit + Co cast details).
• Jack Molloy-Legault portrays Phil Malkin, with his sister Matilda Legault playing Susie Malkin (Rotten Tomatoes official credits).
• Joan Gregson reprised elderly Ingrid Kersh from IT Chapter Two, reportedly her final role before her passing in June 2025 (Wikipedia).

Kid cast details

The young actors make up a significant portion of the ensemble. Clara Stack stars as Lilly Bainbridge, “a girl dealing with her father’s death, absent mother, and guilt” (Wikipedia character summary). Amanda Christine plays Veronica “Ronnie” Grogan, daughter of Hank who befriends Lilly. Blake Cameron James portrays Will Hanlon, son of Leroy and Charlotte and future father of Mike Hanlon, depicted as a science enthusiast struggling in Derry (Wikipedia).

Arian S. Cartaya appears as Rich Santos, a Cuban American boy who befriends Will and has a crush on Marge. Miles Ekhardt plays Matty Clements, a boy who reportedly disappears when Pennywise awakens (Cosmopolitan character guide). Mikkal Karim-Fidler rounds out the kid ensemble as Teddy Uris, best friend of Phil from a Jewish family.

The series weaves together these young performers across different eras, with Will Hanlon serving as a crucial link to the original IT film’s adult Losers.

Will there be a season 2 of Welcome to Derry?

IT: Welcome to Derry has already been renewed for a second season. Production notes confirm Season 2 is officially in development, though full casting details remain limited. The show’s success in exploring Derry’s history suggests future seasons may continue expanding the franchise’s timeline.

Season 2 confirmation

According to available production information, HBO moved forward with Season 2 development following the series premiere. However, specific details about which characters will return or which new actors may join remain scarce at this stage.

Potential season 2 cast

Given that Season 1 covers multiple time periods, Season 2 could potentially explore different eras or continue the narrative beyond where the initial episodes conclude. The question of who might play It in Season 2 remains unanswered in currently available sources, with fans speculating about potential recasting or the return of existing performers.

Why didn’t Bill Skarsgård do Welcome to Derry?

Reports leading up to IT: Welcome to Derry’s production suggested Skarsgård was initially hesitant about returning to the Pennywise role. According to various reports, the actor reportedly didn’t want to return initially before eventually committing to the project.

Reasons for initial hesitation

Skarsgård’s reported reluctance reportedly stemmed from concerns about typecasting and the physical demands of the role. The creature actor had built a diverse career outside of Pennywise and reportedly questioned whether returning to the character would limit his range.

Reasons he returned

Despite initial hesitation, Skarsgård ultimately agreed to return, reportedly motivated by the prequel’s unique storytelling opportunity. The series format allowed him to explore the character differently, with executive producer credits giving him greater involvement in the creative direction. His casting in May 2024 came after months of negotiations, culminating in a deal that positioned him as a central figure in the production.