IT: Welcome To Derry's New Trailer Is Worth Rewatching After That Shining Crossover Reveal, But I Still Think That Jar Of Pickles Is The Freakiest Thing In It

Can you hear the sounds of laughing children as your nose perks up at the smells of popcorn and funnel cakes fill the air? That means Pennywise must be near, and he is indeed present and accounted for in the tension-soaked new trailer for the Stephen King-inspired prequel IT: Welcome to Derry, even if the dancing clown’s actual visage is still yet to be revealed. No matter, as there are plenty of other highlights to get excited about, especially after those rumors about a huge The Shining crossover were confirmed at SDCC.

That’s right, fans’ suspicions about Chris Chalk’s Derry character were revealed to be right on the money, as the Gotham vet will be taking on the iconic role of Dick Halloran, whose ability to shine made him both a hero and a victim in King’s classic The Shining. (The character was famously portrayed by Scatman Cruthers in Stanley Kubrick’s film, and by Carl Lumbly in Mike Flanagan’s Doctor Sleep.) Anyone who hasn’t yet watched the latest full-length preview for the upcoming horror series should hit play now. Just watch out for the pickle jar.

Without a whole lot of context for what to expect from this new group of youngsters hoping to take town the ancient evil that resurfaces in Derry, let's instead hone in on what we know about Dick Halloran's encounters with dark forces located thousands of miles from the Overlook Hotel.

Why Is The Shining's Dick Halloran In IT: Welcome To Pennywise?

Simply put: because Halloran was also in Stephen King's IT novel, which first gave readers crossover delights many years ago. But that only explains the precedence, and not the context of the story making its way to the 2025 TV schedule this fall.

Within the novel, Dick Halloran is one of the founders of The Black Spot, a bar & grill catering to Black soldiers where Halloran also worked as a short-order cook along with Will Hanlon, the father of Loser's Club member Mike Hanlon. (Portraying Will in the HBO series is Javon Adepo.) The establishment was infamously burned down by local racists, possibly guided by Pennywise, and becames a dark stain within both local history and in the memories of those who survived it.

All that said, it's not as if Halloran is a huge character within IT, so the fact that Chris Chalk pops up multiple times in the trailer suggests that his role won't just be limited to the Black Spot's inferno. We even see him discovering one of Pennywise's traveling stage wagon, though its contents are not shown.

I can't wait to see how Dick Halloran's arc is handled in IT: Welcome to Derry, and also to see if that will be the only major crossover character who pops up in the TV series. There's a shot of the Derry Herald newspaper around the :39 second mark that refers to an "Officer Gillespie," which may or may not be a reference to Constable Parkins Gillespie, a minor character in 'Salem's Lot. I'm guessing "not," but it's still a joy to look for details like that.

Speaking of, the image above gives audiences a brief look at Dick Halloran's uniform nametag, which does indeed feature a hastily scribbled surname. So even if the news hadn't been fully confirmed at SDCC, that shot might have been enough to convince everyone.

I Already Believe That Pickle Jar Will Gross Me Out More Than Anything Else In IT: Welcome To Derry

So much footage in the trailer helps set up the general story of this town's evil occurrences and the youths caught up in the middle of it. But then, out of nowhere, along comes this nasty-ass shot of an old and greyed-out hand inside a jar of pickles. It's icky enough in still form, but it's not at all still in the split-second we see it.

No, it somehow starts moving around in there, despite seemingly not being attached to a wrist or forearm or anything else in the realm of organic biology. Show me a bunch of people getting massacred by a clown, and I might not bat an eyelash, but the thought of someone reaching for a pickle and grabbing onto a pair of brined knuckles is apparently where my brain draws the line.

Sure, this is probably just someone's hallucination caused by Pennywise, but if that's the case, then I doubt it'll be the only nightmarish example of gnarled body parts inside sealed food containers. I really don't want to see a big toe poking out of a can of Vienna sausages.

HBO Max somehow still hasn't locked down a specific premiere date yet for IT: Welcome to Derry, but it'll arrive at some point in October, presumably not too long before Halloween.