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.
