If we’ve learned anything from watching the IT movies and the spin-off series, Welcome to Derry, it’s that Derry, Maine is about the last town on Earth anyone should ever visit. Around every corner lurks a creepy, homicidal clown who loves to season his victims with the sweet taste of fear, and that’s not even counting the more mundane but still terrifying evils lurking in this cursed town.
Now that IT: Welcome to Derry has ended its first (but apparently not only) season on HBO Max, the time has come to break down the most horrifying moments featuring Pennywise the Dancing Clown or his various other supernatural manifestations. Check out our ranked list, and let us know your favorite Pennywise scares in the comments below.
Warning: This article contains full spoilers for both IT movies and IT: Welcome to Derry Season 1.
11. Patrick In the Sewer
As seen in: Stephen King’s IT (2017)
How quickly the bully becomes the bullied. This brief but intense scene almost makes us feel a little bad for budding psychopath Patrick Hockstetter (Owen Teague). Patrick chases poor Ben (Jeremy Ray Taylor) into the sewers, eager to cook him with a homemade blowtorch; instead, Patrick discovers the demonic clown living in Derry’s underbelly, and learns that once you enter the sewers, it’s not so easy to find your way out again.
10. Return to the Neibolt Street House
As seen in: Stephen King’s IT: Chapter Two (2019)
We get that the Losers Club members lost many of the memories of their childhood ordeal, but you’d still think they’d retain enough to remember one vital lesson: Never go into the house on Neibolt St. Unfortunately, that’s exactly what the adults do in the sequel, and for their trouble, they’re greeted by the severed, crab-like head of poor Stanley Uris. If any moment in the IT series owes a debt to the great John Carpenter, it’s this one.
9. The Sewer Showdown
As seen in: IT: Welcome to Derry Episode 5 (2025)
Welcome to Derry takes its sweet time actually showcasing Bill Skarsgård’s Pennywise the Dancing Clown, but the villain certainly makes up for lost time in Episode 5. No sooner do Clara Stack’s Lilly and friends follow Miles Ekhardt’s “Matty” into the sewers (an obvious no-no) than their friend reveals himself to be a horrifying clown monster in disguise. Even as the friends scatter into the tunnels in sheer terror, we see the Air Force’s ill-fated mission completely collapse. Worst of all is seeing Pennywise worm his way into Dick Hallorann’s (Chris Chalk) mind and open the terrible box he’s kept sealed there for decades.
8. The Flooded Basement
As seen in: Stephen King’s IT (2017)
Basements are pretty creepy on the best of days, but especially so when you’re talking about old New England houses. This scene really plays on that fear as Bill Denbrough (Jaeden Lieberher) ventures downstairs to find his basement is flooded and hiding the ghost of his dead brother Georgie (Jackson Robert Scott). That’s when Pennywise chooses to make his stomach-churning entrance.
7. Marge the Slug
As seen in: IT: Welcome to Derry Episode 4 (2025)
Few things in horror are more squirm-inducing than scares involving eyeballs; the sheer thought of damaging or losing an eye gives almost anyone the ick immediately. Welcome to Derry’s fourth episode zeroes in on that universal truth when IT manipulates poor Marge (Matilda Lawler) into thinking she’s become a human slug. Watching her lose her mind and attempt to saw off her own protruding eyeballs is not a scene for the squeamish.
6. Georgie’s Death
As seen in: Stephen King’s IT (2017)
The first IT movie opens with a scene that’s very much a statement of intent for the series. We see young Georgie joyfully enjoying the rainy weather with his paper boat, only to happen across a not-at-all creepy clown hanging around a storm drain. In a tamer horror franchise, Georgie’s age would render him immune to any severe consequences, but this is IT, so of course he gets his arm ripped off and is then dragged into the sewer to become the first of Pennywise’s many victims in the movie.
5. Eddie Meets the Leper
As seen in: Stephen King’s IT (2017)
By no means should anyone ever venture inside the dreaded house at 29 Neibolt St., but even wandering around outside can be extremely hazardous to your health. Eddie (Jack Dylan Grazer) learns that the hard way when he walks by the house and encounters Pennywise manifesting as a terrifying leper (Javier Botet). For a kid raised to be a pathological germaphobe, there can be no greater monster.
4. The Hall of Mirrors
As seen in: Stephen King’s IT: Chapter Two (2019)
While most fans agree that IT: Chapter Two is a big step below its predecessor in quality, it does boast one of the most inventive and scary scenes in the series when the adult Bill Denbrough (James McAvoy) finds himself trapped inside a funhouse hall of mirrors. The sheer claustrophobia of that situation would be enough to mine some real fear, but the film goes the extra mile by forcing Bill to watch as Pennywise torments and ultimately eats a young boy who’s also trapped in the maze.
3. The Movie Theater Massacre
As seen in: IT: Welcome to Derry Episode 1 (2025)
As mentioned, the original IT movie starts off by making it clear that no one is safe from Pennywise, not even innocent young children. The first episode of Welcome to Derry goes one step further in its efforts to hammer that point home, closing with a grotesque, horrifying scene where Lilly and her friends are locked inside a movie theater while monsters devour them one by one. Just when we thought the series had introduced 1962’s answer to the Losers Club, It goes and eats most of them for dinner.
2. Inside the House at Neibolt Street
As seen in: Stephen King’s IT (2017)
Once again for the cheap seats: Never go inside the house at 29 Neibolt Street for any reason! The first movie really nails that down when our young heroes venture inside this dilapidated structure and encounter the full scope of Pennywise’s horrors. We’re especially creeped out by the scene where Richie (Finn Wolfhard) is trapped inside a bedroom full of unnerving clown dolls, only to encounter the real Pennywise emerging gleefully from a coffin.
1. Matty Goes Hitchhiking
As seen in: IT: Welcome to Derry Episode 1 (2025)
Welcome to Derry really makes a strong case for itself in its very first episode, delivering some of the franchise’s best scares to date. That includes the best of them all, in an early scene where Matty opts to hitch a ride out of town rather than deal with his abusive home life one minute longer. Unfortunately for him, he winds up stuck inside a ghost car alongside a family of demented ghouls and a mother proudly giving birth – very graphically, we might add – to a demon baby. This is why they always say it’s not safe to hitchhike.
For more on IT: Welcome to Derry, check out IGN’s review of the season finale and see all the easter eggs for the Stephen King multiverse.
Jesse is a mild-mannered staff writer for IGN. Allow him to lend a machete to your intellectual thicket by following @jschedeen on BlueSky.
