Men's Lifestyle November 4, 2025 0 Comments

Where the Hell Is Pennywise Hiding in IT: Welcome to Derry? The Chilling Truth You Didn’t See Coming!

So, where on earth is Pennywise hiding? We’re two episodes into IT: Welcome to Derry—the much-anticipated HBO prequel—and yet, the eerie clown with the unmistakable face paint hasn’t made his grand entrance. It’s almost like waiting for your favorite workout to finally hit the playlist — anticipation building, but still no beat drop. But here’s the twist: Pennywise is coming, and guess what? He’s closer than you might think. You just have to look a bit deeper beneath the surface of this chilling town called Derry, Maine—a place not just haunted by ghosts but by a creeping, generational evil lurking in the shadows every twenty-seven years. It’s like the monster beneath your morning jitters, not always visible but definitely felt. As someone who’s navigated the ebbs and flows of fierce competition, I can’t help but admire the storytelling savvy here—digging back into Stephen King’s layered narrative and carving out a fresh angle that the films left barely touched. So buckle up, because Welcome to Derry promises more than just jump scares; it’s about uncovering the fabric of fear woven into a town that’s very much alive—and yes, Pennywise is poised to make his mark, sooner rather than later… Ready to dive deeper? LEARN MORE

Let’s not beat around the bush here: Where the hell is Pennywise? While Bill Skarsgård is confirmed to reprise his evil clown in IT: Welcome to Derry, we’re now two episodes deep into the HBO prequel series and Pennywise has yet to appear in all his eerie, face-painted glory.

As impatient as some of us may be to see Pennywise again, we can take comfort in two things we know to be true: Pennywise is set to appear in the show, and he’s actually a lot closer than you think. You just need to know where to look.

IT: Welcome to Derry is a prequel spin-off of the two theatrical IT film adaptations, directed by Andy Muschietti. The HBO series homes in on a key theme from the original book by Stephen King. It’s an idea Muschietti’s films didn’t really carve out time to explore, despite the movies’ combined five-hour runtime. In the book, the town of Derry, Maine is haunted. It’s a place quietly possessed by a recurring, generational evil—one that resurfaces every twenty-seven years—known as Pennywise.

Pennywise himself (or more accurately, ITself?) is a malevolent alien presence, one that landed in Derry millions of years earlier. The monster is a shapeshifter whose true form appears to human eyes as golden lights, or “deadlights,” as King calls it. Taking a page from H.P. Lovecraft and the cosmic horror genre, the deadlights compel anyone who sees them driven to madness. Though Pennywise has a preferred target in children, he has no qualms about feeding off the misery and anguish from adults as well. Essentially, Pennywise is a drop of poison in a glass of water. While Pennywise is a concentrated entity, he manifests in all corners of Derry.

But even after reading over 1,200 pages of the King novel, the true nature of Pennywise’s “species” is still unknown. All fans know for certain is that Pennywise manifests every twenty-seven years or so, and that he/it hails from the Macroverse—a dimension that exists far outside ours. (The Macroverse of IT also bridges to other King tales including The Shining, The Mist, and King’s epic fantasy series, The Dark Tower.)

bill skarsgard as pennywise in 'it welcome to derry'

Brooke Palmer//HBO

Bill Skarsgård is set to return as Pennywise in IT: Welcome to Derry. At some point.

For fans of Stephen King’s novel, viewers may recognize that IT: Welcome to Derry is an adaptation of the interludes in King’s IT novel. The interludes are “written” in the book by Mike Hanlon, the one member of the Losers’ Club who stays in Derry and grows up to become a librarian and historian. These sections are structured around Pennywise’s cyclical returns.

As Anthony Breznican reported for Esquire, Welcome to Derry originally evolved from an idea to adapt the interludes that Andy Muschietti, his wife and producing partner Barbara Muschietti, and Bill Skarsgård (also credited as an executive producer) cooked up during the making of IT: Chapter Two. According to the trio, they wanting to craft a prequel that told Pennywise’s origins.

While not an anthology series in the traditional sense, Welcome to Derry is taking an anthology approach to it story with each season themed around the interludes. It may or may not explore the capital-O origins of Pennywise, but it is providing more frightening insight into Derry that was only alluded to faintly in the movies. Each season of Welcome to Derry will center around the past events told in King’s book, “so the seasons would be twenty-seven years in distance from each other,” as Barbara Muschietti phrased it.

While Pennywise has yet to show up, he has certainly “appeared” in Welcome to Derry. The town’s rampant, casual evil is all his doing, even if he isn’t actually on screen taunting a twelve-year-old to death. Skarsgård is also confirmed to return as Pennywise for Welcome to Derry, having appeared in full makeup in the show’s promotional materials. As for why he hasn’t shown up yet? Well, let’s just hope it doesn’t take twenty-seven years.