IT: WELCOME TO DERRY Season 2 Will Unleash a Pennywise Unlike Anything We’ve Seen Before

Pennywise is coming back for more blood in Season 2 of HBO’s It: Welcome to Derry, but don't expect the same killer clown we've come to know. The next chapter of the Stephen King horror series is heading further into Derry's disturbing past, and it sounds like Bill Skarsgård will be bringing something very different to the character.

Returning showrunner Brad Caleb Kane (Crystal Lake) recently spoke with Deadline about the upcoming season and teased that Skarsgård plays “a different kind of Pennywise, Pennywise the way you’ve never seen that character before.“

That's an interesting tease, especially considering where the story is heading next. Season 2 takes us back to 1935, during the Great Depression, and explores one of the most violent events in Derry's history: the Bradley Gang Massacre.

The incident comes straight from Stephen King's It novel and involves a gang of outlaws arriving in Derry, where their criminal activities eventually lead to a bloody confrontation influenced by Pennywise.

Kane describes the second season as something closer to an old-school crime movie, with King's supernatural horror thrown into the mix.

“It’s a Warner Bros. gangster movie. It’s bank robbers and Hoovervilles and street urchins riding the rails religious fundamentalism,” Kane says of the bigger second season.

That's a pretty cool direction for the series. Taking Pennywise into the Depression era opens the door to a different kind of horror, with gangsters, desperate communities, and a town that's already plenty dangerous without an ancient monster feeding on its residents.

As for how far along Season 2 is, Kane confirmed that work is already moving forward: “We’re writing the scripts. We’re about halfway through the writing of the scripts. We have a production schedule, we’re greenlit for a Season 2, and Andy Muschietti’s out there casting.”

The series is working backward through Pennywise's 27-year feeding cycle, exploring the horrific events that have plagued Derry for generations.

The first season took place in 1962, while director Andy Muschietti's It (2017) was set in 1989. It: Chapter Two (2019) then jumped ahead to 2016, when Pennywise returned for another round of terror.

Each cycle is marked by a horrific event, with Pennywise preying on children throughout his time awake. Season 2 will explore the 1935 massacre, but the creative team already has plans to go even further back.

Muschietti previously revealed that Season 3 will focus on the Kitchener Iron Works explosion, a devastating disaster that killed around 100 children during an Easter egg hunt. Fans may remember that the tragedy was briefly referenced through a photograph in the 2017 film.

Interestingly, Muschietti has been teasing this three-season plan since the beginning. The opening credits of IT: Welcome to Derry featured references to several of Pennywise's most infamous atrocities, including the Black Spot Massacre, the Bradley Gang Massacre, and the Kitchener Iron Works explosion. Those were clues to where the series was heading.

What I'm most curious about is how Skarsgård's Pennywise will change in this earlier period. We've already seen how terrifying he can be, but the idea of exploring another side of the character sounds like a great opportunity to do something unexpected with King's iconic monster.

With a 1930s gangster story, a brutal piece of Derry history, and a different version of Pennywise waiting to terrorize the town, Season 2 has some seriously promising material to work with.

Now I just want to know what Kane means when he says we'll see a Pennywise unlike anything we've seen before.

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