Exploring Halloween Parallels in IT and Charlie and the Chocolate Factory

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This October, I’ve found myself drawn to an eerie link between two seemingly unrelated tales: Stephen King’s IT and Roald Dahl’s Charlie and the Chocolate Factory. Despite their contrasting tones—one horror, one whimsy—each story centres on a powerful figure who manipulates children through calculated lures. I’ve been drawn to both stories since I first encountered them around the same time, circa 1992. Pennywise the Clown and Willy Wonka may appear worlds apart, but each tests his young charges in strange, dangerous realms, exploiting weaknesses to reveal something darker. As Halloween brings candy and fear together, it seems these tales might share the same sinister core.


Trickster Archetypes in Whimsy and Horror

The Trickster archetype, embodied in characters like Willy Wonka and Pennywise, is a figure who entices, deceives, and challenges, often blending charm with danger. Tricksters lure others into strange worlds, testing their virtues or weaknesses through calculated schemes. In Charlie and the Chocolate Factory, Willy Wonka embodies a whimsical Trickster, using his factory as a surreal, morality-laced funhouse where each child’s vices lead to their undoing. Pennywise, however, is the Trickster in its darkest form, manipulating fears to exploit and terrorise his young prey.

Roald Dahl, who wrote the screenplay for Chitty Chitty Bang Bang, introduced another iconic Trickster figure: the Childcatcher, an unsettling, gleefully menacing character absent from Ian Fleming’s original novel. So, he has form! Dahl’s Childcatcher is a master of deception, luring children with sweets and promises, only to imprison them—a clear warning against naive trust and indulgence. Through this character, Dahl transformed a whimsical adventure into something darker, cementing the Trickster’s role in cautionary storytelling by amplifying the sinister allure that Tricksters like Wonka and Pennywise wield to captivate, challenge, and sometimes condemn the children who encounter them.

Comparing Wonka and Pennywise

While Wonka may be cloaked in whimsy and Pennywise in horror, both characters are rooted in manipulation and control, pulling children into environments tailored to reveal their deepest traits. Wonka’s actions and tests echo moralistic fables, testing the virtues of his guests under the guise of fantastical charm. Pennywise’s manipulation is darker, exploiting fear itself; he confronts each child with their worst trauma, feeding on their fear to break down their resilience. Despite their differences, both Pennywise and Wonka display a fascination with exploiting innocence—Wonka by exposing the children’s moral failings, and Pennywise by wielding their inner fears against them.

Performances: Tim Curry as Pennywise and Gene Wilder as Willy Wonka

Tim Curry and Gene Wilder’s portrayals of Pennywise and Willy Wonka contribute immensely to the unsettling magnetism of their respective characters. Curry’s Pennywise in IT (1990) balances cheerful charm with primal menace, switching from friendly clown to monstrous predator with disarming ease. Curry captures the twisted trickster essence, exploiting the innocence of children by adopting a persona they trust, only to weaponise it. His nuanced, unpredictable shifts between joviality and terror epitomise Pennywise’s deadly allure, cementing Curry’s performance as a core part of IT’s psychological horror.

Gene Wilder’s Willy Wonka in Willy Wonka & the Chocolate Factory (1971) similarly oscillates between whimsy and veiled cruelty. Wilder’s Wonka toys with the expectations of those around him; his detached wit and cryptic remarks amplify the unease beneath the factory’s colourful surface. With a veneer of eccentricity that masks a strict moral code, Wilder embodies Dahl’s critique of excess and selfishness, becoming both playful creator and unyielding judge. Wilder’s ambiguity and charm make Wonka’s tests feel unpredictable and suspenseful, blending gentleness with the chilling indifference that underscores Wonka’s judgmental nature.

Together, Curry and Wilder bring an element of psychological complexity to their characters, blending menace and charm to show two tricksters who both delight in, and terrify, their audiences.

Lures and Entrapments

Wonka’s chocolate factory, with its vibrant colours and candy-coated promises, is an irresistible playground that shifts quickly into a series of moral gauntlets. Each room within the factory is a carefully constructed test (Saw anybody?), designed to ensnare children based on their unique flaws, with punishments just as surreal as the temptations that led them there. Augustus is punished for gluttony, Violet for vanity, etc. In contrast, Pennywise’s lair beneath Derry—a dark, winding maze of sewers—is a psychological death trap, filled with manifestations of each child’s specific fears. Pennywise exploits these weaknesses not for moral redemption, but to instil dread and ultimately feed on his victims’ vulnerability.

By creating worlds that exist as lures in themselves, Wonka and Pennywise make it clear that neither fun nor fear are safe. Their carefully constructed realms become tests of character, pitting children’s naivety, insecurities, or lack of restraint against forces far beyond their control. In this way, both the factory and the sewer emerge as arenas where innocence is first exploited, then tested, and ultimately transformed, showing two sides of the trickster’s dark fascination with human nature.

Derry’s Sewers vs. Wonka’s Factory

Stephen King’s Derry sewers function as a mirror of the children’s darkest fears, transforming into horrific scenes based on their personal traumas. Each corner of Derry’s underworld is Pennywise’s playground, where supernatural control replaces any safe or familiar aspects of reality, creating a claustrophobic horror that shapes the Losers’ Club’s journey. For Eddie, Derry transforms into a vision of sickness with the leprous hobo, mirroring his fear of contamination. Bill’s grief over Georgie’s death manifests through terrifying apparitions like the flooded basement. The house on Neibolt Street and locations like the fridge at the dump become focal points where Pennywise uses familiar spaces to exploit each child’s fears.

This transformation of Derry illustrates how the town itself, shaped by Pennywise’s influence, amplifies each child’s insecurities and trauma, turning mundane parts of the town into horror-filled locations designed to weaken them psychologically.

Similarly, Wonka’s factory—though far from physically threatening—warps the laws of logic with surreal rooms designed as moral tests. Wonka controls these spaces to exploit each child’s particular vice or failing, where an innocent temptation—a chocolate river, a gum that won’t lose flavour—becomes a pathway to punishment. Both settings shift from enticing to dangerous, showing children that indulgence or misjudgment can carry severe consequences.

Cautionary Atmosphere

The settings amplify each story’s warning against giving into primal fears and vices. In IT, King leverages horror to warn that fear and trauma, if left unacknowledged, can become internal demons. Derry’s sewers strip away each child’s defences, forcing the Losers to rely on courage and friendship to escape Pennywise’s grip. By contrast, Dahl’s factory uses whimsy as a mask for menace, cautioning children against greed, selfishness, and thoughtlessness. The factory’s morality is exaggerated but serves as a stark lesson that indulgence without self-awareness can be one’s undoing. Through these cautionary atmospheres, both King and Dahl place their child protagonists in environments where innocence alone is not enough; survival demands not only purity but self-control and a clear moral compass.

Both settings reveal how darkly magical worlds can test and shape young minds. Where Pennywise’s sewers encourage growth through overcoming fear, Wonka’s factory insists on the value of moral restraint, warning readers that curiosity or indulgence without caution can have lasting impacts. Through twisted landscapes of horror and fantasy, these worlds stand as psychological proving grounds, where reality’s bending tests children’s true characters.

In IT, Derry’s transformation into the children’s fears serves both as a source of horror and as a twisted didactic force, pushing each child to confront their internal struggles in ways that parallel the moralistic function of traditional fairy tales, such as Hansel and Gretel. Just as the witch’s candy house tempts and ensnares, Derry’s familiar spaces—like the house on Neibolt Street or the fridge at the dump—become sites of dark trials, each revealing the children’s fears and vices.

Pennywise’s power to turn Derry into a hostile, psychological battlefield is similar to the way moral tales instruct through consequence. In the same way that Hansel and Gretel are forced to confront the witch’s house as both temptation and threat, each child in IT faces manifestations of their inner demons, from Eddie’s contamination fears (symbolised by the leprous hobo) to Bill’s guilt over his brother’s death (embodied in the vision of Georgie).

This theme in IT reflects the didactic tradition in literature, much like John Bunyan’s The Pilgrim’s Progress or Gulliver’s Travels, which use fantastical or exaggerated settings to convey moral or personal growth lessons. King modernizes this narrative function, blending horror with the bildungsroman: rather than delight alone, IT uses fear as a powerful force to teach resilience and communal support, emphasizing the importance of confronting trauma rather than avoiding it.


Tests of Character

In Charlie and the Chocolate Factory and IT, each child’s central flaw or fear forms the foundation of their journey. Roald Dahl and Stephen King use these weaknesses to shape lessons, delivered through Wonka and Pennywise’s unique forms of trickery, and reveal how innocence or resilience might survive—or fail—under pressure.

Comparison of Charlie Bucket and Bill Denbrough

Charlie Bucket from Charlie and the Chocolate Factory and Bill Denbrough from It are both young, kind-hearted boys who exhibit exceptional resilience in the face of hardship, each emerging as a hero in his own story. Charlie, living in poverty, embodies humility and selflessness; despite his difficult circumstances, he remains optimistic, displaying a quiet strength that ultimately wins him Wonka’s admiration and the inheritance of the factory. His goodness contrasts sharply with the flaws of his peers, whose greed and selfishness lead to their downfall.

Bill, on the other hand, is haunted by the traumatic loss of his brother, Georgie, which drives him into a fight against the malevolent force of Pennywise. Where Charlie’s story centres on moral challenges and rewards for virtue, Bill’s journey is one of courage, loyalty, and the confrontation of deep fear. He becomes the natural leader of the Losers’ Club, guiding his friends in their stand against Pennywise, showing that his strength is not only in resilience but in his ability to inspire others.

Both characters represent a type of innocence that is tested and transformed. Charlie’s trials are moral, set in a surreal candy-coated world that critiques selfishness and excess. Bill’s journey, however, is far darker, confronting literal and figurative demons that threaten his life and his friends. Where Charlie’s reward is the promise of a better life, Bill’s victory over Pennywise offers no such finality but does solidify the power of friendship and bravery. Together, they represent different facets of youthful innocence: one rewarded for maintaining purity of heart, the other strengthened by the necessity of confronting darkness.

Facing Flaws and Fears

Each child in Wonka’s factory embodies a specific vice: Augustus’s gluttony, Violet’s vanity, Veruca’s greed, and Mike’s obsession with technology. These traits set up moral tests that, with each child’s inevitable failure, deliver Dahl’s cautionary message against overindulgence. Wonka doesn’t simply condemn the children; he transforms their desires into physical consequences, such as Violet’s bloated “blueberry” form. The tests are whimsical but unsparing, suggesting moral failing as both avoidable and self-imposed.

Conversely, IT’s children face the inner traumas and fears Pennywise weaponises against them. Beverly’s abusive father, Bill’s grief over Georgie’s death, and Eddie’s anxieties become psychological battlefields, forcing each character to confront the terrors Pennywise amplifies. These battles carry a harrowing weight, requiring the Losers to conquer their fears directly rather than receiving external punishment. King’s focus on internal bravery makes the Losers’ victories less about purity and more about resilience, revealing the transformative power of confronting trauma directly.

Rewards and Consequences

The outcomes for passing or failing these tests reveal each story’s distinct stance on character and survival. In Wonka’s factory, Charlie’s humility and kindness grant him the ultimate reward: inheriting the factory. His triumph highlights Dahl’s belief in simple goodness as the highest virtue, while the others’ failures reinforce the inevitable punishment for unchecked flaws. In IT, success is harder won and less materially rewarding. The Losers’ collective bravery drives Pennywise into temporary retreat, sparing them immediate harm. But King doesn’t promise a clean victory—the traumas they endure leave lasting scars, suggesting that facing fears brings growth yet exacts a permanent toll.

Both tales show that navigating inner weaknesses and facing fears head-on shape survival. Dahl’s world leans on moral absolutes with clear winners and losers, while King’s insists that strength comes from bearing the unresolved weight of human frailty, rewarding growth rather than moral purity. Through Wonka’s candy-coated moral tests and Pennywise’s horrific confrontations, both stories underscore how flaws and fears, when tested, reveal each character’s true mettle.


Friendship vs. Isolation: Bildungsroman, the Ensemble Cast, and the Collective Journey

At the heart of IT and Charlie and the Chocolate Factory are contrasting visions of the childhood journey to self-discovery. Both serve as bildungsroman tales that reveal moral and psychological truths through each protagonist’s journey, yet the trials they face reflect vastly different values. Where IT celebrates the resilience of friendship, Charlie and the Chocolate Factory champions humility and personal restraint. These texts explore themes of societal influence, with Dahl sharply critiquing postwar American consumerism and King delving into collective strength against fear.

Dahl’s portrayal of American consumerism and moral decay in Charlie and the Chocolate Factory is starkly illustrated through characters like Mike Teavee, who embodies American ideals of excess, violence, and media consumption. In the novel, Mike’s obsession with gangsters and his imitation of them while wielding toy pistols signal a critique of American culture’s embrace of materialism and sensationalism. Dahl’s novel could be said to serve as a cultural artefact, revealing his unease with postwar American consumer culture that often prioritized entertainment and indulgence over moral restraint.

In contrast, King’s IT also serves as a bildungsroman tale but emphasizes friendship as an antidote to fear, setting it apart from Charlie and the Chocolate Factory, which champions self-restraint and humility as essential values. In IT, King’s focus on friendship as a communal defence against trauma reveals a different societal message—one about the importance of unity and shared resilience, perhaps reflective of American values around community in the face of adversity. Together, both texts serve as cultural mirrors, revealing the moral, psychological, and cultural values that shaped their respective authors and the societies they critique.

The Losers’ Club is a tightly bonded group, their unity reminiscent of ensemble casts in classic British children’s literature, like Enid Blyton’s Famous Five or Secret Seven. Each child in the Losers’ Club brings a distinct personality and struggle, yet they are bound by their shared experiences and mutual reliance. This interdependence, forged in the face of shared trauma and terror, amplifies their courage, transforming their collective fears into resilience. King’s use of an ensemble cast allows each character to face individual fears with the backing of their peers, a communal strength that makes Pennywise’s psychological games less isolating. For the Losers, friendship is both a shield and a foundation for individual bravery. As each child confronts their trauma, the support of the group functions as a reminder of their own worth and identity, countering the terror Pennywise amplifies.

In Charlie and the Chocolate Factory, isolation plays a different role. Wonka’s factory separates children not only from each other but also from the moral guidance of their families, laying bare their vices in a carefully constructed testing ground. Each child’s self-centered behaviour leads them into traps, symbolising a lack of camaraderie and humility. Charlie, in contrast, approaches the factory tour with curiosity and patience. Rather than seeking immediate gratification, he shares his humble victories with his family, and his modesty contrasts with the Golden Ticket winners’ competitive attitudes. His quiet endurance ultimately earns him Wonka’s approval, highlighting Dahl’s moral vision that true growthThe article ties together Stephen King’s IT and Roald Dahl’s Charlie and the Chocolate Factory through the shared archetype of the trickster: Pennywise and Willy Wonka both manipulate children in surreal, perilous worlds that lure and test. Wonka’s factory contrasts sharply with Pennywise’s lair, using whimsy to underscore moral flaws, while IT examines trauma through horror. Friendship in IT highlights the strength of unity, while Wonka’s isolated tests spotlight humility. Ultimately, both tales underscore childhood’s complexity, the value of resilience, and the hidden costs of innocence.

Ultimately, both It and Charlie and the Chocolate Factory remind us that innocence is often tested by forces far darker than they first appear. As Halloween approaches, dive deeper into these tales and consider how resilience, humility, and friendship help overcome even the most sinister challenges.

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