Scariest Pennywise Moments Ranked

True horror has always been about corrupting the concept of "good." Like the sadistic demon that takes the form of a nun in "The Conjuring" franchise, a brand new house becoming a death trap due to a malevolent presence, or Freddy Krueger attacking victims in the safe space of their dreams, horror relies on subverting classic archetypes of "good" things in new, gruesome ways. 

Therefore, it comes as no surprise that one of the most enduring subsections of villains in horror is the "Evil Clown" archetype — the murderous entity that appears in the smiley form of a laughing jokester wearing colorful clothes and bright makeup. No evil jester is more infamous that Pennywise the Dancing Clown. After first appearing in Stephen King's 1986 novel "It," Pennywise quickly became the best-selling author's most popular character. 

Naturally, Hollywood soon came calling, and "It" was adapted for both the big screen and small. After first manifesting itself in a 1990 TV mini-series starring Tim Curry as the clown, filmmaker Andy Muschietti took a stab at King's novel decades later, releasing a hugely-successful two-part film saga in 2017 and 2019, this one with Bill Skarsgård taking on the role of Pennywise to chilling effect. Here are some of the scariest moments from those later movies, when Pennywise showed why he remains one of horror's most compelling icons. 

One of the best bits involving Pennywise comes during his introductory scene. A little boy named Georgie (Jackson Robert Scott) plays with his paper sailboat on the streets of Derry, Maine one rainy day. The boat glides into a sewer drain, and when Georgie goes to retrieve it, he sees the eyes of a strange creature looking back at him from inside the drain.

Thus, Georgie and the audience are introduced to the main villain of the movie, who identifies himself as Pennywise the Dancing Clown. Despite affecting a friendly demeanor, there is clearly something off about Pennywise as he stares at Georgie for just a second too long, with eyes that bulge and huge teeth that glisten in an unsettling manner. 

Despite Georgie's clear misgivings, he reaches out to retrieve his sailboat, which Pennywise offers back to him. That is when the clown's true nature is revealed as Pennywise opens wide its maw to reveal several rows of pointed teeth and chomps down on Georgie's arm. The next few minutes are particularly terrifying as Georgie screams and struggles, all to no avail as Pennywise drags him down into the depths of the sewer.  

Even though Pennywise is the main villain of the story, it is repeatedly made clear that the adults of Derry in general are awful, awful people. The town is filled with racists, abusers and homophobes, and a chilling example of that last group occurs at the start of "It: Chapter Two" with the death of Adrian Mellon (Xavier Dolan-Tadros) at the hands of a group of thugs for the crime of being out publicly with his boyfriend.

The thugs brutally attack Adrian and his boyfriend and throw Adrian into the river. His boyfriend runs desperately to the bank of the river and tries to locate Adrian. That is when he sees a man has already found Adrian and fished him out of the river. The momentary relief turns to renewed fear when the savior looks up, and it is revealed to be Pennywise himself. 

Looking directly at Adrian's boyfriend (and the audience), Pennywise proceeds to chomp down on Adrian's still-moving body. Other horror movies might have chosen to have Pennywise attack the thugs as a bit of karmic payback, but "It: Chapter Two" makes it clear that Pennywise is a completely amoral being who has no interest in punishing the guilty, only satisfying its hunger with whichever victim happens to be nearest.  

While other killers in slasher films rely on exotic weaponry to strike fear into their victims, Pennywise makes do with simple red balloons. Throughout the story, these helium horrors float around Derry on their own, a recurring motif of the "clown whimsy" that Pennywise so effectively subverts to make his victims feel afraid.

One of the quietest moments of horror in "It" is when Ben (Jeremy Ray Taylor) goes to the library alone to try to uncover the truth about Pennywise. While Ben pores over books, we see a solitary red balloon silently making its way across the room. To add to the feeling of unsettlement, the balloon disappears, but is replaced by an old lady who can be see watching Ben intently with a predatory gaze. 

The scene underlines just how powerful a creature Pennywise is, who can become anyone, anything, and show up anywhere to terrorize it's victims. It is only then, after Pennywise has had fun watching Ben trying to understand its real nature, that the evil clown kicks things up a notch to terrorize the little boy with a race around the library's underground archives, taking on the appearance of a headless corpse.

Bill (Jaeden Lieberher, later James McAvoy) is generally seen as the central protagonist of "It" and its sequel. Therefore, it seems only natural that Bill was one of the first main characters to come into contact with Pennywise, due to the clown killing Bill's little brother Georgie which sets the events of the story into motion. 

Wracked with guilt and haunted by his own role in Georgie's death, Bill is amazed to see Georgie in their house's flooded basement one night. Even as Bill tries to grapple with what he is seeing, it becomes clear that this is not the real Georgie. That is when Pennywise appears in the basement, silently moving its mouth and hand to conduct Georgie's performance like a gruesome marionette.

Once Bill realizes the clown is the true threat, Pennywise drops the charade and runs towards Bill. The clown's movements are particularly unnerving as it appears to move in an odd, herky-jerky manner. The action underscores that while Pennywise might look like a demented clown, it is in reality something much more alien and unfathomable.  

Pennywise's whole thing is that it likes to make victims afraid before eating them, because the fear makes them tastier. To that end, Pennywise did not merely want to eat the members of The Losers Club (Bill Denbrough and his allies), but also to terrify them as much as possible first. Which is why it lured the Losers into the Neibolt house. 

First, Pennywise made sure the Losers were split up so they could not draw comfort from each other's presence. Then, the evil clown began unleashing mind games on each individual member of The Losers Club. Richie (Finn Wolfhard) found himself stuck inside a dark "Clown room" filled with all manners of creepy dolls and puppets. To make it worse, there was a coffin at the end of the room containing a maggot-infested doll bearing Richie's likeness.

After Richie had enough and tried to escape, Pennywise himself jumped out of the coffin with an animalistic snarl and gave chase. Richie only barely managed to make it out of the room. Even though the clown room only made one appearance in the films, it remains one of the most disturbing set pieces from the series. 

As the Losers come into closer contact with Pennywise, they begin to uncover its mysterious origins. Although the movie does not give any definite answers about the nature of the creature that calls itself Pennywise, it is confirmed that the thing is extraterrestrial in nature. There is no perhaps more horrifying indication of this than its use of the dreaded "Deadlights."

The Deadlights are a writhing form of extra-dimensional energy that appears as three balls of orange light swirling around in an all-encompassing darkness. The Deadlights are Pennywise's true form, one it takes when it wants to break a person's mind, since the human brain cannot even begin to comprehend the Deadlights without going mad or shutting down completely. 

We see this happen firsthand when Pennywise exposes Beverly (Sophia Lillis) to his true form. At first, Beverly tries to stay defiant. But then the clown horrifically peels back its face and its rows of sharp teeth to expose the Deadlights, leaving Beverly comatose and floating unconscious in Pennywise's lair. The most chilling part is that you can hear the screams of other children that had also fallen victim to Pennywise, emanating from the Deadlights.  

The only good thing that can be said about Pennywise is that it is an equal-opportunity murderer. It does not only prey on the weak and the broken, but also those who consider themselves strong and tough. Like Henry Bowers (Nicholas Hamilton) and his gang of bullies who relentlessly torment The Losers Club at every opportunity. 

One of Bowers' most loyal allies was Patrick (Owen Teague), whose desire to mess around with other children led him into the sewers where Pennywise lived. Patrick quickly realized he was in way over his head when an army of dead children started following him. Even Patrick's homemade flamethrower did nothing to stop the children, who were previous victims of Pennywise.

Just when Patrick thought he had seen the worst, a single red balloon began floating towards him. The balloon popped, and there was Pennywise standing in front of Patrick in all its terrible glory. Needless to say, that was the last anyone saw of him.  

"It: Chapter Two" saw The Losers Club return to Derry as adults to put an end to Pennywise once and for all. But the clown had its own plans in store for them, and a fresh new set of horrors to terrify them with. One that was created specially for Beverly (Jessica Chastain) was Mrs. Kersh, who claimed to be the new tenant of Beverly's old home. 

Kersh invited Beverly into her old home and offered to make them both tea. At first Beverly was reluctant, but the old woman's sweet demeanor won her over. As the two conversed about various things, Beverly was gripped with a growing conviction that something was terribly wrong. Sure enough, she soon noticed an old photo of Bob Gray, the man whose identity Pennywise assumed a long time ago.

As Beverly attempted to leave, Mrs. Kersh returned in a demonic form, with elongated appendages and a shriveled face. To add to the horror, Beverly saw the monster as Bob Gray putting on his clown makeup before tearing into its own skin to add the red lines to its face. The scene showed that the last time The Losers Club had defeated Pennywise as children had not deterred the evil clown one bit, and it was just as capable of toying with the Losers and leaving them completely terrified.  

Even though it was an alien entity, the eons it has spent on Earth have made Pennywise deeply familiar with the worst parts of human nature, and it has exploited that knowledge again and again to torture its victims on an emotional level. No member of The Losers Club suffered this kind of abuse worse than Beverly, due to her own personal circumstances. 

When teenaged Beverly came home one day, she thought she heard the voices of children coming from the sink. When she tried to investigate, long tendrils of hair shot out of the sink, spouting blood all over Beverly and the bathroom. That is when her father entered the room and saw Beverly cowering in the corner. When Beverly tried to tell him what happened, he couldn't see the blood.

The scene gave viewers a terrifying look at the clown's power. Not only can Pennywise terrorize children, but it has also the adults in Derry unable to see such torments. Beverly is left broken and sobbing alone on the bathroom floor, realizing how much more alone she is than the other children, because she can't even rely on her own father for help.

Henry Bowers was already all kinds of messed up when he was a regular school bully. But he truly descended into the depths of full-fledged psychopathy once Pennywise decided to use the young delinquent as its personal pawn. To that end, Henry found a present from It in his mailbox: a brand new switchblade. 

Armed with his new prize, Henry made his way home to find his father sleeping in front of the television. As Henry stared down at his prone father, a kid's show started playing on the TV. The host of the show encouraged Henry to take his father's life, which he did by opening the blade directly into the old man's neck. 

That is when the host of the show stepped aside to reveal Pennywise sitting among a crowd of its young victims, all shouting at Henry to find the rest of the Losers and "Kill them all!" Henry then embarked on his demented quest to fulfill Pennywise's wish, landing him in a mental asylum in Derry. There, he would be tortured with visions of clowns and corpses for the next 27 years.

In most cases, Pennywise prefers to attack its victims one by one instead of all together, since it needs them to feel alone and afraid. But there was one time that the clown chose to jump right into the middle of a meeting of The Losers Club when the kids were at their most united. 

After Bill first started to suspect that the creature used the town's sewers to get around and hide in secret, the Losers gathered in his garage to go over the evidence together. That was when Bill and his friends first realized the extent of the clown's omnipresence in Derry, as the slide projector took on a life of its own. Family pictures from Bill's past started appearing on the screen, as one gradually morphed into an image of Pennywise.

Kicking the projector over did not help. Pennywise appeared in person in the garage in the form of a giant. The only reason the children were able to escape was because Pennywise was still toying with them, since it did not yet consider them a true threat. This giant form of Pennywise would later be referenced in the sequel's ending, when the clown becomes a half-human, half-spider behemoth in its final battle against the Losers.   

Throughout the movies, Pennywise introduces itself as "The Dancing Clown." But we don't get to see much of the dancing, what with the creature busy maiming, mauling and generally terrorizing its victims into a quivering mess. At the end of the first movie, however, we get to see the dance in action, and it is every bit as freaky as everything else about Pennywise.

After Beverly is taken by Pennywise into its secret lair in the sewers, she awakens to find herself in a giant room filled with centuries-old debris. Suddenly a jack-in-the-box springs open, a caravan door falls out, and we see Pennywise dancing to out-of-tune carnival music. 

While the rest of the clown's body kicks and stomps, its face manages to stay weirdly still, further emphasizing the fact that its physical body is merely a puppet-like façade that does not obey the laws of the human anatomy. 

You would think since the Losers were all grown up in "It: Chapter Two," there would be an easing up on all the terrorizing and murder of children. But the film actually has two such scenes, both more gruesome than what we saw in the first one. When an adult Bill chases a kid into the hall of mirrors at a fair, for instance.

Since Bill knows the child is in danger, he desperately tries to find him, but is repeatedly blocked by all the mirrors and reflections. Meanwhile, we see that Pennywise has already entered the scene and is silently stalking both Bill and the child. To add to the confusion, the child sees Bill as a threat, and shouts at him to go away. 

While Bill tries to convince the child he means no harm, Pennywise appears, dragging a creepily-long tongue across the glass casing separating Bill from the child. Pennywise starts cackling and breaking the glass with its head, as Bill pleads with it to leave the child and take him instead, all to no avail. The clown finally breaks the glass and opens its maw wide, engulfing the screaming child in a single, gory bite. 

In "It: Chapter Two," we meet Vicky. She was a little girl who was self-conscious about a prominent birthmark on her face. One night while watching a game in an open air stadium, Vicky was entranced by a single firefly that danced and glided in front of her. Vicky followed the firefly into the darkest corner under the stadium benches, where she saw a strange red-haired clown waiting for her, who introduced itself as a friend. 

What followed was a horrifying example of the kind of emotional manipulation and cruelty Pennywise employs on its victims. First the clown played on the little girl's sympathy by pretending to cry and saying no one wants to be its friend. It then offered to "blow away" the birthmark from Vicky's face so the other children wouldn't make fun of her anymore. 

After Vicky was convinced and drew near to Pennywise, the clown's demeanor suddenly changed. The friendly smile dropped, drool appeared on its chin, and the creature prepared to feed on the unsuspecting child. Even as the little girl attempted to prompt her new friend to fix her birthmark, It chomped down, and Vicky joined untold other Derry children that Pennywise had sent floating into the Deadlights.