Welcome to Derry Could Have Unraveled a Lingering Pennywise Enigma

Pennywise's influence on the children of the Derry series molds them long into adulthood, transforming them into the very adults who perpetuate the community's cycle of hatred alive. The creature preys most easily on children from broken households — youngsters who often mature to replicate the identical behaviors as their parents. However, the Hanlon household stands apart as a rare example of a family unit that never splinters, which could clarify why Mike Hanlon, even after choosing to stay in Derry, persists as the sole member who doesn't completely succumb under the clown's influence.

Hanlon Household's Unique Resistance

In the fourth installment of the series, Leroy at last grows more aware of the supernatural forces surrounding the community, especially when It starts haunting his son, Will, during their fishing trip. The Hanlon family comprises some of the few grown-ups who are aware that things are not right with the town, notably the father, who was revealed to be sensitive to the Shining when he was capable of sensing a fellow psychic's employment of it in the third episode. Later, Leroy sees one of Pennywise's signature balloons outside his house. The ability, coupled with his failure to experience terror, along with the base of his household, may be why he's able to see Pennywise's hauntings. However, consider if that psychic sensitivity is hereditary, and one of the reasons Mike is among the few individuals in the town who resisted succumbing to the town's malevolence?

Will is part of the collective of kids at his school being tormented by Pennywise. His classmates hail from dysfunctional families, with parents who don't believe they're being targeted. The reason Will is being pursued is due to the viciousness of the community, paired with his likely receptiveness to psychic abilities, which makes him susceptible. This family are ultimately outsiders in the town during 1962, which lends itself towards the family feeling anomalies exist about the town from the beginning. Additionally, they possess a good foundation that remains unbroken, in contrast to the folks who originate in the area, with bonds that have decayed internally.

Backstory Connections

Drawing from the It novel, we understand the juvenile Will will end up at the Black Spot, where the psychic will save him from a blaze that the local KKK members of the community will cause. In the recent film, we observe that he has a boy named Mike and that Will ultimately dies in a configration, with Leroy outliving his own child and taking his grandson in. The public account in the motion picture is that the parents were on drugs, but given our current view of him in the series, that's difficult to accept. Maybe the shy youth, once he grew up, leaned into drink to rid himself of the hauntings, or perhaps the rotten environment got to him initially, with the KKK ultimately completing the task it began long before. Whether through the fear of the entity or via the cruelty of the town, seeded by It, the creature in the end gets the final victory on Will.

Leroy's Transformation

These occurrences would clarify how Leroy changes so drastically from what we witness in It: Chapter 1 and the prequel. In his later years, he seems resentful and much harsher with his parenting. Because he outlived his own son, it's understandable to see such a profound shift. Nonetheless, his words carry more weight now that we know he's witnessed the clown's activities and the impacts they wrought upon his son. In the opening scene of the movie, we see the boy pause to use a bolt gun on a animal at Leroy's farm. Leroy chastises him for hesitating and offers an analogy that results in a kill-or-be-killed situation.

“There are two places you can be in this existence. You can be out here like us, or you can be in there,” he says as he gestures to the creature. “You waste time indecisive, and another is going to decide for you. But you won't know it until you experience that bolt in your head.”

In hindsight, this could be a bit of foreshadowing, a lesson he regrets not imparting to his own child. Perhaps he desires he had acted differently in his youth, but for certain factors, he couldn't resist the sickening attraction of Derry.