Debuting on HBO and HBO Max in October 2025, a brand new trailer for Pennywise prequel series IT: Welcome to Derry was unveiled at San Diego Comic Con 2025, and it’s already one of the scariest things I’ve watched this year. The show will take us back to where it all started in the 1960s, where the town of Derry is haunted by evil, and unbeknownst to them, a killer clown who just happens to be responsible for all the missing kids.
If you’re trying to figure out the full timeline, the 2017 movie version of IT was set in 1988, with follow-up film IT: Chapter Two taking place 27 years later. Bill Skarsgård has played Pennywise in all three projects, and he’s aged incredibly well if the fleeting prequel footage is anything to go by. We know how his story ended, but its beginnings are still shrouded in mystery, and that mystery is probably absolutely hideous.
We’re not going to see The Losers’ Club this time around, but that doesn’t mean IT: Welcome to Derry will be devoid of other Stephen King movies lore. In fact, I noticed an epic crossover in the new trailer, and if you missed it, rest assured the sneaky Easter egg is staring you directly in the face.
IT: Welcome to Derry’s new trailer nods to Stephen King’s most upsetting story of all time
Not content with merely scaring us silly over the last few decades, King’s also enjoyed reducing us to tears too. The Shawshank Redemption is one of the most famous examples of this, adapted as a film in 1994 to explore the bond between two men imprisoned in Shawshank. Why is this relevant? Because 57 seconds into the IT: Welcome to Derry trailer above, you’ll see a bunch of male prisoners on board a bus reading ‘Shawshank State Prison’ along its navy side.
It’s a blink-and-you’ll-miss-it moment, but it’s also the kind that will make horror movie fans gasp the moment they see it. We’ve got no idea what role (if any) the prison could play in the new TV show, but from the way the trailer sets up the significance of the bus, it might be more than a mere Easter egg. Two of our new juvenile Pennywise hunters come across our bussed-off prisoners in fear-striken-awe, with the killer clown’s signature red balloon floating along a riverbank nearby directly after.
This could easily mean Pennywise is a former Shawshank inmate, except instead of making a 90s movie that could reduce you to tears just by thinking about it, he decided to harm innocent children instead. The fact Pennywise’s backstory is basically all to play for might just be the most intriguing part of IT: Welcome to Derry, purely because we’ve simply got no bearing on what might be coming. What could be scarier than the fear of the unknown?
Will we see even more Stephen King Easter eggs as the TV show starts airing? Who knows. But thanks to this sneaky scene, I’ll be keeping my eyes peeled like the armchair detective I was born to be.
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