Pennywise Is Back: It: Welcome to Derry Trailer Teases Bill Skarsgard’s Most Terrifying Turn Yet—and Reminds Us We’ll Float Again

Happy nightmares, y'all—tonight’s top story is engineered to haunt you.
The clown is back. HBO dropped a fresh look at 'IT: Welcome to Derry', and yes, it is very much a Pennywise trailer: lots of blood, stray limbs, and a sharp-toothed goofball lurking where he loves to lurk most — down in the sewer.
So what is this thing showing?
The teaser jumps between two tracks: a younger crew (think an early version of the Losers Club) set around 1962, and a group of adults who are just as rattled. One of those adults is Leroy Hanlon, played by Jordan Adepo. If that last name rings a bell, it should — Leroy is the father of Mike Hanlon, who eventually becomes a core Loser. In the show, Leroy ends up stationed in Derry on military duty, which is about the worst assignment you can imagine if you value sleeping through the night.
There is a full-on Army sweep of the sewers — guns up, flashlights cutting through the dark — that goes sideways fast when Pennywise pops out dressed like a zombified Uncle Sam. It is both on-brand and deeply wrong in a way the franchise excels at. The clown is all over this teaser in his classic form too, with one perfectly timed jumpscare that got me to blink hard and reassess my life choices.
The behind-closed-doors preview
Before this hit the internet, the trailer played privately at NYCC, where the crowd also saw three scenes from the show. Two of those scenes focused on Dick Hallorann, played by Chris Chalk, and his unusual friendship with Leroy Hanlon. Leroy does not know about Dick's 'Shining' ability yet — which, if you know your Stephen King lore, is a big, glowing can of worms waiting to open. The third scene centered on a character they are still keeping under wraps; you can spot her in the trailer covered in blood and screaming her lungs out.
What you will notice in the teaser
- Timeline bounce: a 1962-era proto-Losers Club paired with a present set of adults.
- Leroy Hanlon (Jordan Adepo) arrives in Derry on military orders, which tees up the town vs. Army tension.
- US soldiers sweeping the sewers run into Pennywise dressed as a decaying Uncle Sam. It goes about how you think.
- Plenty of classic Pennywise shots — teeth, dancing, the works — and one big scare that lands hard.
- NYCC attendees got an extra peek: three scenes, including two featuring Dick Hallorann (Chris Chalk) and his growing bond with Leroy, with Dick's shining still under wraps, and a third scene with a spoiler-y character who shows up in the trailer drenched in blood.
When and where to watch
'IT: Welcome to Derry' premieres on HBO and HBO Max on October 26.