IT: Welcome to Derry Season 2 Will Feature a Never-Before-Seen Version of Pennywise

Pennywise is returning for Season 2 of HBO’s IT: Welcome to Derry, but fans should expect a different take on Stephen King’s iconic killer clown. Returning showrunner Brad Caleb Kane (Crystal Lake) has teased a new version of the terrifying character, played once again by Bill Skarsgård.

Speaking with Deadline, Kane revealed that the upcoming season will introduce a side of Pennywise audiences have never seen before.

Skarsgård plays “a different kind of Pennywise, Pennywise the way you’ve never seen that character before,” Kane teased.

The change makes sense given Season 2’s historical setting and its focus on one of the most disturbing events in the history of Derry.

IT: Welcome to Derry Season 2 Explores the Bradley Gang Massacre

Set in 1935 during the Great Depression, the second season will explore the Bradley Gang Massacre, a horrific event referenced in Stephen King’s novel IT. The story follows a gang of outlaws who arrive in Derry, setting the stage for a bloodbath influenced by Pennywise.

Kane described the upcoming season as a major departure in tone and setting, drawing inspiration from classic gangster films.

“It’s a Warner Bros. gangster movie. It’s bank robbers and Hoovervilles and street urchins riding the rails, religious fundamentalism,” the showrunner explained.

The new setting will bring a different historical atmosphere to the series while continuing to explore the evil lurking beneath Derry’s seemingly ordinary surface.

Kane also provided an update on the show’s progress, confirming that Season 2 is officially 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,” he revealed.

The History of Pennywise Continues in Season 2

The timeline of IT: Welcome to Derry is built around Pennywise’s recurring cycle of violence. According to the mythology established in King’s novel and the film adaptations, the entity awakens approximately every 27 years to feed, with children among its primary victims.

The first season took place in 1962, while Andy Muschietti’s IT (2017) was set in 1989. Its sequel, IT: Chapter Two (2019), jumped forward 27 years to 2016, continuing the story of the Losers’ Club as adults.

By moving back to 1935, Season 2 will explore an earlier chapter in Derry’s bloody history, revealing more of the horrifying events connected to Pennywise’s recurring appearances.

The Bradley Gang Massacre is one of several tragedies woven into the franchise’s larger timeline, and its adaptation could provide further insight into how the entity’s influence has shaped the town across generations.

Andy Muschietti Teases the Long-Term Plan for IT: Welcome to Derry

Series developer and producer Andy Muschietti has previously discussed a larger plan for the show, with the story designed to explore different periods in Derry’s history.

Muschietti has indicated that a potential third season would focus on the Kitchener Iron Works explosion, another devastating event referenced in King’s IT.

The catastrophe took place during an Easter egg hunt, when an explosion claimed the lives of approximately 100 children. The tragedy was briefly referenced through a photograph in Muschietti’s 2017 IT adaptation.

The show’s opening credits also offered clues about this broader timeline, featuring imagery connected to three notorious events: the Black Spot Massacre, the Bradley Gang Massacre, and the Kitchener Iron Works explosion.

Those references helped establish the historical framework behind the series, hinting at the different eras the creative team could explore as Pennywise’s story unfolds.

For now, Season 2 is progressing through script development, with casting underway. Although a premiere date has not yet been announced, Kane’s comments suggest that the next chapter will offer a substantially different take on Pennywise while expanding the mythology of Derry.

Stay tuned to GoreCulture for further updates on IT: Welcome to Derry Season 2.

What do you think a different version of Pennywise will look like in Season 2? Let us know in the comments below!