20 Creepiest Pennywise Quotes From The IT Movies & Miniseries, Ranked

This article contains mention of homophobia and violence.

Throughout the IT movies and miniseries, Pennywise's quotes offer bone-chilling reminders of why he is one of the most memorable horror movie villains. Author Stephen King is one of the most prolific horror writers of all time as he can create monsters that tap into the most basic human fears. While many great Stephen King adaptations exist, perhaps the best-known are the movies IT (2017) and IT Chapter Two (2019), as well as the 1990 IT miniseries. This centers on a group of friends called the Losers Club who go up against a shape-shifting alien called IT.

IT wakes up every 27 years, tormenting the town of Derry, Maine. The monster takes the form of a victim's worst nightmares, feeding off their fear. Throughout both the movies and the miniseries, IT's most common form is that of Pennywise the Dancing Clown. Played by Bill Skarsgård in the movies and the upcoming prequel TV series Welcome to Derry, and Tim Curry in the miniseries, Pennywise manages to torture many little kids with his appearance and words. Many of Pennywise's quotes throughout the adaptations are terrifying enough to induce nightmares in the bravest souls.

20 "See You In Your Dreams."

IT Miniseries (1990), Said To Eddie

Tim Curry As Pennywise rising out of a drain In the IT Miniseries

There's often a debate around whether Tim Curry or Bill Skarsgård were better as Pennywise. While Skarsgård definitely brought something unique to the role, there are just as many creepy Pennywise quotes which can be attributed to Tim Curry in the 1990 IT miniseries. One of these comes when Pennywise manifests in front of Eddie while the boy is taking a shower.

Eddie might be physically fine at this point, but psychologically the damage has already been done.

After Pennywise claws his way up through the grate in the floor, he begins to taunt Eddie, telling him that he "just wanted to say hello". While the whole sequence is terrifying and unsettling, it's the moment that Pennywise tells Eddie "see you in your dreams" that makes for the creepiest quote in the monologue. It speaks to the fact that none of the Losers Club, or indeed, the population of Derry, can ever truly escape the evil clown. Even if Eddie survives the encounter, he'll be haunted by traumatic visions of Pennywise forever more - and Pennywise knows it. Eddie might be physically fine at this point, but psychologically the damage has already been done.

19 "If You Don't Believe, Close Them And See."

IT Chapter Two (2019), Said To Beverly

Bill Skarsgard As Pennywise with clown makeup on In IT Chapter 2

Of all the members of the Losers Club, Beverly is especially tormented by Pennywise in 2019's IT: Chapter Two. In fact, one of the creepiest scenes in the entire sequel to IT specifically focuses on Pennywise going out of his way to torment her personally. This particular creepy Pennywise quote from IT: Chapter Two comes when Bev visits the house of Mrs. Kersh to discover more about the origins of Pennywise and, in doing so, hopefully find a way to stop his 27-year cycle of tormenting Derry once and for all.

"Run, run, run. You haven't changed anything yet. You haven't changed your future. You, you haven't saved any of them. Close your eyes, Bev." - Pennywise in IT: Chapter Two

Unfortunately for Bev, she's played right into Pennywise's hands. Everything in the house, including Mrs. Kersh herself, are simply illusions or different forms of Pennywise that he's conjured to lure Bev into a false sense of security. This creepy Pennywise quote comes right at the end of the terrifying encounter. It's one of the demonic clown's most harrowing for a key reason - it robs Bev of all sense of hope. Daring Bev to close her eyes and see the inevitable doom in her future creates the distinct sense that everything the Losers Club is doing is simply part of Pennywise's plan, and that he's been toying with them the entire time.

18 "People Always Make Fun 'Cause Of The Way I Look."

IT Chapter Two (2019), Said To Vicky

Bill Skarsgard as Pennywise smiling In IT

One of the most harrowing death scenes in both movies or the 1990 miniseries comes in 2010's IT: Chapter Two. It's when a young Derry girl, Vicky, encounters Pennywise underneath the bleachers at a high school football game. Completely unaware of the danger she's in, Vicky makes the mistake of approaching Pennywise and engaging with him. Pennywise tells Vicky that he is her friend to lure her in, but Vicky is skeptical. "If you're my friend," she asks, "why are you hiding in the dark? You're not my friend, you're scary..."

Had she simply turned and ran, Vicky may have survived. Unfortunately, she makes the mistake of asking a follow-up question - "Why are you crying?" This is when Pennywise responds with an incredibly, incredibly creepy quote - especially in the context of speaking to a little girl as young as Vicky:

"People always make fun ‘cause of the way I look. I thought if you couldn’t see my face, maybe you'd want to be my friend. Nevermind… Oh, silly ol' Pennywise, you'll never have no friends." - Pennywise in IT: Chapter Two

This Pennywise quote is so scary because it serves as a reminder of who, and what, the evil clown truly is. He's a predator that prays on children. He uses Vicky's insecurities about a birth mark to win her confidence, after which she's promptly devoured.

17 "Do You Have Prince Albert In A Can?"

IT Miniseries (1990), Said To Richie

Pennywise in the Library in the IT miniseries

One of the most terrifying aspects of Pennywise, no matter the version of the character, is that he always gives the distinct sense that he's (for lack of a better term) playing with his food. He likes to taunt and toy with his victims before devouring them. This happens multiple times in IT and IT: Chapter Two, as well as in the original Stephen King novel. However, it's Tim Curry's version of Pennywise in the 1990 IT miniseries that best plays on the fact that Pennywise is a clown.

Of all the creepy Pennywise quotes from the miniseries, the moment when Tim Curry's take on the killer clown demon manifests to Richie in a library, filled with people, is perhaps the moment that best plays on Pennywise's tendency to taunt his prey with humor. He actively tells Richie a joke, leaving Richie (and many viewers) incredibly unnerved. To make the moment even more terrifying, Richie quickly realizes that nobody else in the library can see Pennywise, making it clear that even when surrounded by others, he isn't safe.

16 "All Those Sit-Ups!"

IT: Chapter Two (2019), To Ben

Pennywise taunting Ben in IT Chapter Two

Pennywise is always at his scariest in any version of IT when he turns the attempts of the Losers Club to increase their chances of survival against them. Of the many creepy Pennywise quotes, it's the moment when he harasses Ben in IT: Chapter Two which best showcases this terrifying aspect of the demonic character. Ben, who was overweight as a child, had spent his life after first encountering Pennywise getting in shape. Pennywise knows this, and is quick to make Ben feel like all his efforts were for nothing.

"All that success, all those sit-ups! But deep down, still just a fat, fat, fatty loser! Who always knew he would die alone!" - Pennywise in IT: Chapter Two

Not only does Pennywise mockingly let Ben know that his increased fitness won't make him any safer, he also unearths Ben's surpressed self-image issues. Of all the times Pennywise plays on the insecurities of the Losers Club in any version of IT, this is by far the most brutal - especially when Pennywise reminds Ben of his deeply rooted fear that he'll die alone.

15 “Hiya, Georgie.”

IT (2017) and IT Miniseries (1990), Said To Georgie

The first line said by Pennywise in both IT and the IT miniseries is, “Hiya, Georgie.” While the words on their own aren't terrifying, they become one of the creepiest lines when examined in context. Pennywise is talking to Georgie from inside the sewage drain, a location that nobody should be. The little boy never tells the monster his name, making it eerie that he knows. What's more, the specific way of greeting Georgie sounds casual, friendly, and familiar.

This contrasts with his unnerving physical appearance and tone of voice – which subtly hints at the shape-shifting monster's sinister intentions. While Pennywise is attempting to lure Georgie close enough so he can strike, the line also highlights the darkly playful way Pennywise speaks to his victims. Georgie is unaware of the danger at this moment, but even when the victims are aware, Pennywise enjoys playing this game with them and acting like a friendly clown.

14 "Why Him? Because You Weren't There, Billy!"

IT Chapter Two (2019), Said To Billy

Bill Skarsgard as Pennywise in IT Chapter Two

Georgie's death is not only a shocking and disturbing way to kick off the story, but it also serves as a moment that will haunt Bill Denbrough for the rest of his life. He is filled with guilt over the loss of his younger brother, seen both in the first movie as well as the sequel, where it becomes clear that even in adulthood, Bill has not gotten over the trauma. As expected, this is something that Pennywise latches onto and constantly tortures Bill with.

In It: Chapter Two, there is a sequence in which Bill imagines visiting the sewer where Pennywise grabbed Georgie. He breaks down into tears and in anger, crying out loud as to why it had to be Georgie who was taken. As Bill gets up to leave, Pennywise's voice answers the question. He further taunts Bill with the same guilt-ridden idea that has been in his mind for years —if Bill had been there with Georgie, maybe he'd still be alive.

13 "Beep Beep, Richie."

IT (2017) and IT Miniseries (1990), Said To Richie

IT is one of the best horror movies about a group of friends, as the Losers Club makes for an endearing team of heroes. They are outcasts who come together to make each other feel better and stronger in the face of their everyday struggles as well as the growing threat of Pennywise. Of course, it fits into Pennywise's sadistic ways that he even uses this friendship against the heroes when he begins targeting them.

"Beep beep Richie" becomes a recurring line in the franchise that the other characters say to Richie Tozier. It serves as a comical warning whenever Richie is going too far. However, when the friends are exploring the derelict house, Pennywise surprises Richie and repeats the line to him before attacking. It serves as a chilling tease that Richie and the others have gone too far in investigating Pennywise and he is after them now. It also shows that he is watching them closely.

12 "Or... Just Leave Us Be."

IT (2017), Said To The Losers Club

Pennywise holds his hand over Bill's mouth in IT's ending

Pennywise has been around for centuries, but the Losers Club proves to be formidable enemies for the evil entity. However, the brutal monster doesn't just attack the young heroes — he also looks to tear apart their psyches and destroy them as a group. When the heroes are in the sewers, Pennywise manages to grab Bill while the others surround him and prepare to fight.

Pennywise begins by threatening them all with the horrific deaths that await them when he finally gets them all, but then he offers them a dark deal instead. He tells the others that they can simply allow him to take Bill for his final meal before his sleep and Pennywise will leave the others to live long and happy lives. It is a chilling way to fracture the group, as these young kids want nothing more for the horror to end.

11 "You Will Be."

IT (2017), Said To Beverly

Pennywise's sadistic glee in tormenting his victims is unsettling, but it becomes even scarier when he takes a more serious tone. Among the Losers Club, Beverly seems to be the most confident and strong of the young heroes and she proves it even when she is taken by Pennywise to his sewer lair. While Pennywise grabs Beverly by the throat, she tells him that she is not afraid of him.

While it is a somewhat cliché horror movie villain line, it does conjure up a lot of fear about what else Pennywise might do to ensure he can feast on this child's fear.

In a subtle moment of Pennywise's vulnerability, he seems to sense that this is true.He twitches in frustration, but instead of this seeming like a triumphant moment for Beverly, it becomes more frightening with how angry Pennywise seems at this revelation, and he promises that he will change that. While it is a somewhat cliché horror movie villain line, it does conjure up a lot of fear about what else Pennywise might do to ensure he can feast on this child's fear.

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