IT girls, IT boys, IT corpses: Who’s who in Derry?
The new HBO series Welcome to Derry drops viewers into 1962 Maine, where a military family, a clutch of outcast kids, and an ancient evil converge long before the Losers Club forms. With Bill Skarsgård back as Pennywise, a Hallorann crossover, and a Season 2 renewal already locked, the question of who’s who matters more than ever. Here is the cast breakdown that ties every thread together.
Hanlon family anchors the timeline
Jovan Adepo plays Major Leroy Hanlon, a Korean War veteran whose transfer to Derry sets the first season in motion. Leroy’s quiet authority and growing suspicion of the town give the story its adult spine.
Taylour Paige portrays Charlotte Hanlon, a schoolteacher and activist whose instincts sense something wrong long before the disappearances hit the headlines. Paige has spoken about the 1962 pressure to suppress those instincts, a tension that colors every scene she shares with her on-screen husband.
Blake Cameron James rounds out the household as young Will Hanlon, the future grandfather of Mike. His friendships with the other kids form the earliest version of the Losers dynamic and keep the Hanlon bloodline front and center.
Young outcasts shape the horror
Clara Stack stars as Lilly Bainbridge, recently released from Juniper Hill Asylum after her father’s death. Lilly’s first vision of Pennywise kicks the mystery into gear and establishes her as the group’s reluctant oracle.
Amanda Christine plays Ronnie Grogan, daughter of the local projectionist. Ronnie’s street-level knowledge of Derry’s back alleys supplies the kids with maps, rumors, and the occasional stolen reel of film.
Matilda Lawler appears as Marge Truman, already torn between popularity and loyalty. Lawler’s prior turn in Station Eleven prepared her for the quiet dread Marge carries, and older versions of the character surface in IT Chapter Two.
More kids join the circle
Arian S. Cartaya plays Rich Santos, the quick-witted newcomer who documents every strange sighting in a notebook that later becomes evidence no adult will accept.
Mikkal Karim-Fidler steps in as Teddy Uris, whose family name links the season to Stanley Uris and hints at generational patterns the town refuses to break.
Miles Ekhardt portrays Matty Clements, whose disappearance in the pilot forces the group underground—literally—when they follow a trail of pacifiers into the sewer system.
Pennywise returns with restraint
Bill Skarsgård reprises the role that defined the 2017 and 2019 films, yet the show keeps Pennywise off-screen for long stretches. The restraint lets dread build before the inevitable sewer showdowns.
Skarsgård also appears briefly as Bob Gray in 1908 flashbacks, a choice that widens the timeline without giving away Season 2’s planned 1935 setting.
Executive-producer credit for Skarsgård signals continued involvement beyond Season 1, and early social-media reactions already fixate on how much screen time the clown will receive when the Halloween special drops.
King-universe crossovers deepen the lore
Chris Chalk steps into the role of a young Dick Hallorann, decades before his post at the Overlook Hotel. The casting creates a direct pipeline between Welcome to Derry and The Shining for viewers tracking King’s larger web.
Madeleine Stowe appears as Ingrid Kersh, whose older self shows up in IT Chapter Two. Stowe’s final performance before her 2025 passing adds a layer of real-world gravity to the part.
These links turn the series into more than a prequel; they position Derry as a node in the constant King multiverse conversation that dominates fan forums this fall.
Military brass supply the pressure
James Remar plays General Francis Shaw, Leroy’s superior whose search for a rumored “weapon” collides with the town’s actual predator. Remar’s résumé of hard-edged authority figures makes the character’s Cold War paranoia feel lived-in.
Rudy Mancuso appears as Captain Pauly Russo, the liaison who filters information between the base and Derry’s civilian leadership, often choosing the version that keeps the disappearances quiet.
Stephen Rider rounds out the command structure as Hank Grogan, Ronnie’s father and the town projectionist whose late-night reels inadvertently reveal more than the military wants known.
Local faces fill the gaps
Peter Outerbridge plays Clint Bowers, a town mechanic whose garage becomes an unofficial meeting spot for adults who sense the pattern but cannot name it.
Kimberly Guerrero appears as Rose, a recurring presence whose scenes in the upcoming Halloween special extend the Derry timeline back before 1908.
Thomas Mitchell steps in as Colonel Fuller, the base’s public face whose press briefings grow increasingly hollow as the body count rises.
Renewal and future seasons shift the map
HBO renewed the series after the first season’s debut weekend numbers, confirming an eight-episode Season 2 set in 1935. Showrunner Brad Caleb Kane has said the new Pennywise will look and behave differently, resetting audience expectations once more.
Filming is slated for summer 2027, with a possible late-2027 or early-2028 premiere. Casting for the earlier era is already underway, and social chatter centers on which Season 1 kids might return in older or younger forms.
The 30-minute Halloween special “A Story of Derry,” released October 31, 2026, serves as a bridge, featuring Guerrero and Zahn McClarnon in roles that predate the 1962 timeline and tease the scope of future seasons.
Where the story heads next
The Welcome to Derry cast now stands as the connective tissue between two film timelines, one upcoming season, and a growing list of King properties. Viewers tracking every Hanlon, Hallorann, and half-glimpsed clown can map the entire mythology in a single watch. As scripts for 1935 move into production, the only certainty is that Derry keeps its dead close and its secrets closer.
