Meet the Cast of 'It: Welcome to Derry'

Few horror stories have lingered in our collective pop culture nightmares quite like It. 

Who can forget the image of Pennywise coaxing Georgie toward a street gutter with that bright red balloon? Stephen King’s tale of evil lurking beneath the surface of a small town carved itself into the horror hall of fame decades ago, and Andy Muschietti’s films (It and It Chapter Two) cemented Pennywise as an icon for a new generation. 

Now, HBO pulls us deeper into the mythos with It: Welcome to Derry, a prequel series that expands the terrifying world of King’s novel and the recent films.

Set in the eerie town of Derry, Maine, the new series explores the dark events that unfolded long before the Losers’ Club ever faced Pennywise. 

Developed by the filmmakers behind the movies – Andy and Barbara Muschietti, along with writer Jason Fuchs – the show dives into the haunting history and expands the sinister vision fans already know and love. Andy Muschietti directs multiple episodes, ensuring the series stays true to the franchise’s chilling tone.

Here’s your first look at the cast of It: Welcome to Derry, which premieres Sunday, Oct. 26 at 9pm ET on HBO and HBO Max. Follow this link to add HBO to your DISH package.  Not a DISH subscriber? Follow this link to find the best offer and subscribe to DISH today!

Meet the Cast of 'It: Welcome to Derry'

Jovan Adepo

Audiences may recognize Jovan Adepo from Fences, Watchmen, and The Leftovers, where his layered performances reveal both vulnerability and resilience. In Welcome to Derry, Adepo plays Air Force Major Leroy Hanlon, a new arrival to Derry who becomes one of the first to notice sinister shadows creeping into the town, putting him on a crash course with its disturbing history.

Taylour Paige

After making waves in Zola and earning critical acclaim in Ma Rainey’s Black Bottom, Taylour Paige brings her sharp emotional presence to the series. She portrays Leroy’s wife Charlotte Hanlon, a schoolteacher drawn into the town’s unsettling mysteries when her students start experiencing strange and terrifying visions.

Chris Chalk

Known for his powerful roles in When They See Us, Gotham, and Perry Mason, Chris Chalk has a gravitas that makes him a natural fit for a story steeped in paranoia and dread. He plays Dick Hallorann, a community leader grappling with how to protect Derry’s citizens amid a growing undercurrent of dread. If that name sounds familiar, it’s because Hallorann is also an important character in another Stephen King adaptation: The Shining.

James Remar

James Remar (Dexter, The Warriors) plays General Shaw, a longtime Derry resident and leader of a top-secret project. Stationed at the Derry Air Force Base during the Cuban Missile Crisis, Shaw oversees a classified operation amid Cold War paranoia. Remar’s commanding presence highlights the generational fear and authority shaping Derry’s dark history.

Stephen Rider

From Luke Cage to Daredevil, Stephen Rider has proven he can embody intensity and complexity. In Welcome to Derry, he plays Hank, the operator of Derry’s local movie theater who’s drawn into the town’s secrets. On set, Rider recounted how director Andy Muschietti’s playful use of a bugle became a daily ritual, signaling the crew when they’d successfully captured a scene—a detail that speaks to the camaraderie of the production.

Madeleine Stowe

Beloved for her work in Revenge, 12 Monkeys, and The Last of the Mohicans, Madeleine Stowe returns to TV in a pivotal role. She plays a woman with deep roots in Derry’s past whose knowledge of the town’s dark secrets may hold the key to Pennywise’s origins. Her character anchors the show’s exploration of how Derry’s history and recurring cycles of fear echo through events like the Black Spot tragedy and the town’s lingering legacy.

Rudy Mancuso

Social media star turned actor-musician Rudy Mancuso (Música) brings a new energy to the ensemble. Mancuso plays Captain Paulie Russo, Leroy Hanlon’s ally at the Derry Air Force Base during the turbulent days of the Cuban Missile Crisis—his character’s Cuban heritage becoming an anchor for the anxieties of the era and a connection to larger social and historical themes depicted in the show.

Bill Skarsgård

Of course, no trip to Derry would be complete without the specter of Pennywise himself. Bill Skarsgård reprises his infamous role, embodying the shapeshifting clown whose eerie-as-hell charm and menace define the films. For much of this season, Pennywise’s emergence is held in suspense, with Skarsgård’s involvement kept largely off-set except for key moments. According to the producers, his eventual reveal is orchestrated with the same chilling anticipation as the shark in Jaws, promising to terrify viewers as only Skarsgård can.

The Premiere

It: Welcome to Derry premieres Sunday, October 26 at 9pm ET/PT on HBO and HBO Max. The eight-episode run will release new episodes weekly, leading to a season finale on Sunday, December 14.

Prepare to go back to where the terror first took hold—because in Derry, the past is never truly buried.