Honestly, walking back into the sewers of Derry feels like visiting a childhood home that you know is haunted but you just can't stay away from. After months of "will they, won't they" rumors, the Welcome to Derry casting lineup is finally out in the wild. It's not just a bunch of random faces. We’re looking at a group that has to carry the weight of Stephen King's most messed-up legacy without the safety net of the Losers' Club we already know and love.
The biggest relief for most of us? Bill Skarsgård is back.
There was a minute there where it looked like he might pass the torch. Can you imagine anyone else doing that lazy-eye stare or the drool? It would’ve felt like a knock-off. Thankfully, he signed on to reprise Pennywise, but the rest of the ensemble is where things get really interesting. This isn't just a monster-of-the-week show; it's a 1960s period piece that's trying to explain why this town is so fundamentally broken.
The Hanlon Legacy and the New Faces of 1962
Most people assume this show is just about the clown. It's not. The core of the story actually follows the Hanlon family. If that name sounds familiar, it should—Mike Hanlon was the "librarian" and historian of the Losers' Club. In this prequel, we meet his ancestors.
Jovan Adepo (who was incredible in Watchmen and The Leftovers) plays Major Leroy Hanlon. He’s an Air Force pilot who gets stationed at the base near Derry. He’s joined by Taylour Paige as Charlotte Hanlon. Seeing Adepo in another Stephen King project (he was Larry Underwood in the recent The Stand) feels right. He has this grounded, weary energy that fits perfectly in a town that wants to swallow you whole.
The casting choice here is clever because it bridges the gap between the 1990s/2010s movies and the deeper lore of the book. We’re seeing the Black Spot era—or at least the lead-up to it.
👉 See also: When Was Kai Cenat Born? What You Didn't Know About His Early Life
Why Chris Chalk as Dick Hallorann Changes Everything
This is the "holy crap" moment for the hardcore King fans. Chris Chalk is playing a young Dick Hallorann.
Yes, that Dick Hallorann. The chef from The Shining.
For years, people have debated the "King-verse" connections, and the Welcome to Derry casting confirms that the overlap is very much alive. In the books, Hallorann was part of the Black Spot, a nightclub in Derry that met a grisly end. Chalk is a fantastic actor—you might know him from Gotham or Perry Mason—and he has to play a man who is literally "shining" while a cosmic entity is trying to eat the local kids.
It’s a heavy lift. He has to be the link between the trauma of Derry and the eventual trauma of the Overlook Hotel.
The Kids of 1962: A Different Kind of Losers
You can't have an IT story without a group of kids. But these aren't the Losers. They’re a different breed, living in a much more rigid, military-adjacent environment.
✨ Don't miss: Anjelica Huston in The Addams Family: What You Didn't Know About Morticia
- Matilda Lawler plays Marge Truman. She’s arguably the emotional anchor of the younger cast. If you saw her in Station Eleven, you know she can play "haunted" better than almost anyone her age.
- Clara Stack plays Lilly Bainbridge. She’s the one with the "visions"—the town calls her "Loony" because she spent time in Juniper Hill. Sound familiar? That’s the same asylum Henry Bowers ends up in later.
- Amanda Christine is Ronnie Grogan. Her dad runs the local theater, the Capitol, which is basically the ground zero for Pennywise sightings in the trailer.
These kids aren't just fodder. The showrunners, Andy and Barbara Muschietti, have made it clear that the 1962 timeline is about the "disappearances" that the town tried to forget. It’s a summer show that, due to production delays from the strikes, actually filmed into the colder months. Barbara Muschietti even joked in interviews that they had to change the finale’s climate because the kids were literally growing up too fast during the eight-month break.
What Most People Get Wrong About Pennywise’s Return
There’s a misconception that Bill Skarsgård is just doing a cameo.
Wrong.
He’s a series regular. But the show is digging into the Bob Gray persona. There’s a scene teased involving a flashback to 1908 where Skarsgård plays a "has-been drunk clown" named Bob Gray before the entity fully consumes his form. This is the stuff fans have been dying for. It’s not just the creature; it’s the mask the creature wears and how it became "Pennywise" in the first place.
Skarsgård himself mentioned he was hesitant at first. He didn't want to "milk" the character. But once he saw the scripts for these "juicy" scenes—especially one where Bob Gray talks to the entity as a child—he was in. It sounds like we’re getting a much weirder, more psychological version of the clown than the jump-scare-heavy movie version.
🔗 Read more: Isaiah Washington Movies and Shows: Why the Star Still Matters
The Supporting Cast is Unbelievably Stacked
You’ve got James Remar (the dad from Dexter) playing General Francis Shaw. He’s the guy in charge of the Air Force base. Having a military presence in Derry adds a layer of "authority vs. the unknown" that the movies lacked.
Then there’s Madeleine Stowe. She’s playing Ingrid Kersh. If you’ve seen IT Chapter Two, you know the name Kersh. Is she the same Mrs. Kersh who turned into a giant naked monster in front of Beverly Marsh? Probably not the same person, but definitely a relative. It’s these little name-drops that make the Welcome to Derry casting feel like a reward for people who actually read the 1,000-page book.
The Full Primary Cast Breakdown
- Bill Skarsgård – Pennywise / Bob Gray
- Jovan Adepo – Major Leroy Hanlon
- Taylour Paige – Charlotte Hanlon
- Chris Chalk – Dick Hallorann
- James Remar – General Francis Shaw
- Matilda Lawler – Marge Truman
- Clara Stack – Lilly Bainbridge
- Rudy Mancuso – Captain Pauly Russo
How to Prepare for the Premiere
The series is officially streaming on Max (formerly HBO Max). Since it’s a prequel, you don't strictly need to rewatch the movies, but it helps to refresh yourself on the history of the Hanlon family and the Black Spot.
Pay attention to the background characters. The Muschiettis love hiding Easter eggs in the casting. If you see a character with the last name Bowers, Marsh, or Tozier, keep your eyes peeled. The show has already hinted that Matilda Lawler’s character might have a surprising connection to the Tozier family tree, which would explain a lot about the "visionary" traits seen in later generations.
To get the most out of the new season, look for the following:
- Watch for the Capitol Theater scenes; they seem to be the focal point for the 1962 "feeding cycle."
- Listen for mentions of the "Turtle" or "Maturin"—the creators have teased that the cosmic side of the lore will get more screen time here than it did in the films.
- Keep an eye on Dick Hallorann’s interactions with the kids. It’s likely he’ll be the one to explain what’s actually happening to them before the military steps in.
Derry is a town that remembers everything and forgets nothing. With this cast, it looks like we're finally going to find out why.
Next Steps for Fans:
Start by revisiting the "Interludes" in Stephen King's original IT novel. Most of the 1962 events in the show are expanded versions of the stories Mike Hanlon’s father told him. If you want to spot the cameos before they happen, that’s your best roadmap. Check the Max schedule for weekly episode drops, as this isn't a "binge-all-at-once" release—they're letting the tension simmer.