Derry’s darkest history is about to get even more terrifying as Pennywise is heading back to 1935
Just when audiences thought they had begun to understand the horrors lurking beneath the seemingly ordinary Maine town, IT: Welcome to Derry is preparing to turn back the clock for a new chapter steeped in crime, bloodshed, and supernatural terror. This time, the story moves to 1935, during the Great Depression, as Pennywise’s reign of terror intersects with one of the most notorious incidents in Derry’s history.
Showrunner Brad Caleb Kane has offered an early tease of what viewers can expect from Season 2, suggesting that the upcoming installment will take a dramatically different approach from its predecessor. While specific plot details remain under wraps, Kane’s comments point toward a chilling combination of classic gangster cinema and the unsettling mythology created by horror master Stephen King. And if his description is any indication, Derry’s past is about to become a whole lot bloodier.
A Great Depression Nightmare With a Gangster-Cinema Twist
Speaking with Entertainment Weekly, Kane revealed that Season 2 will explore a different visual and storytelling palette, transporting viewers to 1935. Rather than simply repeating the atmosphere established in the first season, the creative team is drawing inspiration from Warner Bros.’ classic gangster pictures, reimagined through the sinister lens of Pennywise and King’s fictional universe.
The setting offers a striking opportunity to blend two different forms of terror. The Great Depression was an era associated with economic hardship, desperation, and organized criminal activity, creating a world where fear and uncertainty were already part of everyday life. Introduce a supernatural entity that feeds on fear, and the result could be a particularly unsettling chapter in Derry’s history.
Kane has also confirmed that Season 2 is already in development, with the writers’ room actively working on the next installment. Although he has kept the central storyline a mystery, he described the season as extremely bloody and emphasized that it will feel very different from Season 1. That promise of a new direction is intriguing. Rather than relying solely on familiar horror imagery, the series appears poised to use the aesthetics of a gangster film to build a period-specific nightmare in which human violence and supernatural evil collide.
The Bradley Gang Takes Center Stage
At the heart of the new season is the Bradley Gang, a group of criminals whose story forms part of Derry’s disturbing history in King’s novel IT. In the book’s account of the 1930s, George and Al Bradley lead the gang, with George’s wife, Kitty Donahue, accompanying them during their robberies. The group becomes associated with a series of crimes across Derry, including robberies targeting stores and banks.
Their story reaches a violent conclusion in 1935, when townspeople ambush the gang during a shootout and kill its members. But this is Derry, where even the darkest events carry a deeper sense of dread. According to King’s novel, Pennywise is present during the incident.
That detail creates a fascinating foundation for Season 2. The Bradley Gang’s story already contains the ingredients of a classic crime drama: dangerous criminals, a frightened community, and a violent confrontation. By placing Pennywise within that history, the series can transform a notorious event into something far more disturbing.
Was the gang simply another chapter in Derry’s cycle of violence, or did the creature’s presence make the tragedy even more sinister? The series has plenty of room to explore how Pennywise influences the town and how its residents respond to horrors they may not fully understand. For viewers familiar with King’s novel, the historical connection offers a tantalizing clue about where the story could lead. For newcomers, it provides a dark mystery rooted in the town’s past.
Pennywise’s Reign Of Terror Continues
One of the most fascinating elements of the IT mythology is the way Derry’s history seems to repeat itself. Horrific events recur across generations, and the town’s residents often appear unable or unwilling to confront the darkness surrounding them.
Season 1 explored an earlier chapter of that cycle through its 1960s setting. By moving to 1935, the next installment has an opportunity to dig further into the history of Pennywise’s influence and show audiences another period in which the creature’s presence intersects with human tragedy.
The earlier timeline also reinforces the franchise’s central idea that Pennywise is not just a monster waiting for a group of children to cross its path. In fact, its connection to Derry stretches across decades, making the town itself an essential part of the horror.
With the Bradley Gang storyline providing a historical framework, Season 2 could examine how fear spreads through a community already facing hardship, violence, and uncertainty. The gangster-film influence may deliver a different atmosphere, but the underlying terror remains unmistakably IT.
Will Bill Skarsgård Return As Pennywise?
Naturally, one of the biggest questions surrounding the new season is whether Bill Skarsgård will return to his role as Pennywise. The actor’s portrayal of the terrifying entity has become closely associated with the modern IT franchise, making his potential return a major point of interest for fans.
However, no official Season 2 cast announcement has been confirmed in the information currently available, and Skarsgård’s return remains unconfirmed as well. Until the production makes an announcement, viewers will have to wait for further details about who will lead the next chapter. The same goes for the season’s premiere date. Although development is underway, an official release date has not yet been announced.
For now, Kane’s comments provide the clearest indication of the creative direction made up of a 1935 setting, a story connected to the Bradley Gang, a classic gangster-film influence, and a season that promises to be bloody and distinct from what came before.
Welcome Back To Derry If You Dare
With its move into the Great Depression, IT: Welcome to Derry Season 2 has the potential to expand the franchise in a bold new direction. The combination of historical crime, Stephen King’s mythology, and Pennywise’s terrifying presence creates an opportunity to explore a different side of the town’s past without losing the supernatural dread that defines the series.
The Bradley Gang’s story offers a grim historical backdrop, while the gangster-cinema influence promises a fresh visual identity. Most importantly, the season’s earlier timeline gives the creative team another opportunity to show how Derry’s darkness reaches far beyond any single generation.
There are still plenty of unanswered questions, from the returning cast to the exact shape of the story. But with the writers already hard at work, the next chapter is beginning to take form. And as we know, in Derry, the past never stays buried and Pennywise has had a long time to perfect his return.
