Welcome to Derry cast: every main character and how they fit the IT prequel

The world of Pennywise returns in Welcome to Derry, a 1962-set prequel that traces the town’s rot decades before the Losers Club. The cast mixes fresh faces with familiar mythology, anchoring the story in one family’s arrival—and the evil that wakes to greet them.

Main cast and characters in Welcome to Derry

Bill Skarsgård — Pennywise
The shapeshifting entity resurfaces in an era of small-town smiles and simmering fear. Expect fewer taunts and more silent dread early on, as the creature tests Derry’s newest vulnerabilities.

Taylour Paige — Charlotte Hanlon
A determined mother adjusting to a new town, Charlotte becomes the moral center of the story. Her protective instincts frame several early confrontations with Derry’s “accidents.”

Jovan Adepo — Leroy Hanlon
An army major and Charlotte’s husband, Leroy brings discipline and skepticism to a place that punishes both. His presence ties the series to a lineage fans will recognize.

Blake Cameron James — Will Hanlon
Their son, Will, offers the audience’s view of Derry’s schoolyard hierarchies and the first hints that not every nightmare is imaginary.

James Remar — General Shaw
A rigid authority figure whose agenda intersects with town politics. His decisions ripple through the Hanlons’ prospects of fitting in—or escaping.

Stephen Rider — Hank Grogan
Part of Derry’s working backbone, Hank moves inside the gray zone between knowing too much and saying too little.

Matilda Lawler — Marge
A perceptive kid whose curiosity outpaces her safety. Scenes around her often carry the show’s most unnerving “is something behind me?” energy.

Amanda Christine — Veronica “Ronnie” Grogan
A friend group linchpin; Ronnie’s courage and quick thinking become crucial when adults dismiss the strange as coincidence.

Clara Stack — Lilly Bainbridge
Soft-spoken but observant, Lilly senses patterns others miss—particularly around missing children.

Arian S. Cartaya — Rich
Streetwise, loyal, and the first to joke in a crisis, Rich helps decode Derry’s unspoken rules.

Miles Ekhardt — Matty Clements
A newcomer who doesn’t grasp how fast Derry punishes missteps, making him a magnet for Pennywise’s earliest games.

Mikkal Karim-Fidler — Teddy Uris
A name that raises eyebrows for book and film devotees; Teddy threads connective tissue to a family line audiences already know.

Jack Molloy Legault — Phil Malkin and Matilda Legault — Susie Malkin
Siblings whose home life mirrors Derry’s outward charm and inward rot; their chapter broadens the town’s social web.

Chris Chalk — Dick Hallorann
Yes, that Dick Hallorann. His inclusion extends the larger universe, and his sensitivity to the uncanny becomes a compass when rational explanations fail.

Peter Outerbridge — Clint Bowers
Part of a dynastic scourge within the town, setting up generational echoes that longtime fans will recognize immediately.

Madeleine Stowe — (recurring role)
A poised presence whose influence crosses social strata, complicating the Hanlons’ attempt to read which doors in Derry are safe to knock on.

Key recurring players

• Rudy Mancuso — Captain Pauly Russo: A uniformed voice who embodies the town’s official narrative—useful when fear needs filing away.

• Additional recurring names surface across the early episodes, filling in school corridors, factory floors, and municipal offices where denial does its most efficient work.

How the Welcome to Derry cast connects to IT lore

• The Hanlon family: By foregrounding Charlotte, Leroy, and Will, the series seeds the legacy of a surname that matters later. Their arc reframes how memory—and the suppression of it—takes root.

• The Bowers thread: With Clint in the mix, viewers see how cruelty can be cultivated long before it’s personified by the next generation.

• Dick Hallorann’s bridge: His presence isn’t a cameo stunt; it positions the story on a broader map of places where certain people hear certain rooms “speak.”

• Teddy Uris’ surname: A deliberate echo that teases fate, family, and the way Derry cycles victims back through its machinery.

Ensemble dynamics: why this lineup works

Welcome to Derry leans on a dual-engine cast: adults who feel the pressure to rationalize, and kids who can’t. The Hanlons carry the emotional core, but the perimeter roles—teachers, officers, town leaders—show how institutions help Pennywise without ever seeing the clown. Performances are calibrated to a period tone: restrained, polite, and then suddenly frayed when the mask of normalcy slips.

Character guide at a glance

• Pennywise: predator testing limits, not yet at full spectacle.

• Charlotte & Leroy Hanlon: parents fighting gaslight and gossip as much as monsters.

• Will Hanlon, Ronnie Grogan, Marge, Lilly, Rich, Matty, Teddy, Phil, Susie: the web of kids who map Derry’s dangers faster than the grown-ups.

• General Shaw, Hank Grogan, Clint Bowers: power, labor, and lineage—three levers the town pulls when it needs order more than truth.

• Dick Hallorann: a lighthouse presence; when he speaks softly, listen.

What to watch for next

• Shifts in point of view: Early chapters favor the kids; midseason attention tilts to parents forced to confront the impossible.

• The cost of denial: Characters who explain away the first horrors tend to pay later, sometimes in public, sometimes where no one will admit it happened.

• Name echoes and family trees: If a surname tingles your memory, there’s a reason—track how the show plants those roots.

Whether you come for the mythology or the performances, the Welcome to Derry cast is built to make the town feel alive—and then show you how it eats.