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Welcome to Derry Season 1 Ending: All Pennywise & IT Twists, Stephen King Changes, Cameos & Season 2 Setup

IT: Welcome to Derry Season 1 ends with multiple twists that not only wrap up the events of this story, but also set up Season 2 and make major changes to Pennywise lore. The first season of the IT prequel has already had some dramatic and devastating moments, not least the burning of The Black Spot, but it still finds room for more in the finale, “Winter Fire,” which serves as the culmination of the entity’s latest cycle of fear and violence. Warning: Contains SPOILERS for IT: Welcome to Derry Season 1, Episode 8.

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With Pennywise having immediately awoken from his slumber and taken the kids of Derry, the race is on to stop him. It’s a twisty, slightly convoluted episode that sees Lilly, Marge, and Ronnie attempting to put the shard of It’s cage back in place to re-seal the boundary that traps Pennywise inside Derry, while the military actively works against that, wanting to free It because they believe fear is the key to controlling people. Ultimately, this generation of “Losers” is able to save the day, but it’s guaranteed that It will be back.

How Pennywise Was Defeated & When It Returns

Pennywise (Bill Skarsgård) in IT Welcome to Derry Season 1 Episode 8

Pennywise is almost defeated by Dick Hallorann, who uses his shining abilities to try and entrap the creature. Dick freezes It, forcing it into 1908 after it took over Bob Gray, but without any powers. This is seemingly similar to the mental lock box that we saw of Dick’s earlier, a place to keep bad shines, or spirits. Unfortunately, while it works for a little while, it’s not enough against an entity as powerful as It, and Pennywise is able to break free.

With that, then, it requires getting the shard, or dagger, back in place. This will reunite all the pillars, and mean that Pennywise cannot leave Derry and is forced back into his sleep cycle. this itself is no easy feat, not only with It back on the attack, but because the shard itself resists: the further it’s taken from what is essentially it’s “home” on Neibolt Street, where the cage with It inside landed, the more it tries to pull back, corrupting the minds of those using it and try and do its bidding.

It’s only by all of the kids coming together and working as one (including the spirit of Rich Santos) that they can defeat Pennywise, reinforcing the power of friendship and mirroring the Losers Club defeating Pennywise in the IT movies. That’s something that, chronologically, is still to come (even if Pennywise is aware). Welcome to Derry‘s timeline is 27 years before IT: Chapter One, and so with It back in its rest cycle, that movie is when it next awakens.

Why Sophia Lillis’ Beverly & Mrs. Kersh Return In Welcome To Derry’s Ending

Sophia Lillis as Beverly Marsh in IT
Image courtesy of Warner Bros. Pictures

After Pennywise’s defeat and the closing moments, IT: Welcome to Derry delivers what is essentially a post-credits scene, with a flashforward to 1988. That itself is surprising enough, but what’s even more shocking are the cameos from IT movie actors Sophie Lillis and Joan Gregson, who play Beverly Marsh and the elderly Mrs. Kersh, respectively.

Ingrid Kersh’s fate had been left up in the air heading into the finale, but the end reveals that while she technically survived her encounter with Pennywise, her mind was left completely altered. We see the younger version of the character in Juniper Hill Asylum, before it cuts to 1988 and the elderly version is still there, painting pictures of clowns, showing that the loss of her father and encounters with Pennywise still haunt her.

After that, we get what is a prelude to the IT movies – this is just a few months before Chapter One – as Kersh makes her way into another room, where we see another Juniper Hill resident has hanged themselves, while a man and a girl cry in front of the body. It’s revealed that the dead woman is Elfrida Marsh, the mother of Bev, and Lillis reprises her role as the latter. She’s pushed away by her father, a sign of his abusive nature, but Kersh attempts to provide some comfort, saying “no one who dies in Derry truly dies.”

This is the exact phrase that would be spoken to the adult Beverly (Jessica Chastain) when she’s confronted by It in IT: Chapter Two, wherein it takes the form of Mrs. Kersh. Welcome to Derry completely recontextualizes that scene, because it shows that the form of Kersh was deliberately chosen as the most effective form of torture against Beverly, as a horrifying reminder of the darkest moment of her life. The music in the scene – Max Hansen’s “Det er det skønneste jeg ved” – is also the same as the one in the movie, driving the point home.

Welcome To Derry Confirms Marge Is Richie Tozier’s Mom

Marge in IT Welcome to Derry and Richie in IT
Images via HBO/WB

One of the biggest theories about Welcome to Derry has been that Marge Truman is the mother of Losers Club member Richie Tozier. This first started to gain traction when it was confirmed her full name was Margaret, the same as Richie’s mom, as confirmed by Stephen King’s novel (though she goes by Maggie). There were some other clues as well, including similar glasses and a clear shared sense of humor and silliness. But the real kicker came after Rich sacrificed his life to save Marge at The Black Spot, with the pair professing their love for one another.

Was Richie thus named to honor Marge’s tragic childhood love? The answer is a resounding yes, with no room left for ambiguity. Pennywise outright refers to her as Marge Tozier, before saying she’s not Tozier “yet.” Because he sees time differently, he’s aware of the future, and knows that Marge will go on to become Richie’s mother, and that he’ll be among those who contribute to his ultimate downfall. This not only adds an extra, tragic layer of depth to Richie’s character, but makes the Losers’ eventual victory a win for Marge, and full vengeance at last for Rich’s death.

Pennywise’s “Time Travel” Abilities in IT: Welcome to Derry

Pennywise (Bill Skarsgård) covered in blood in IT Welcome to Derry's Season 1 finale
Image via HBO

Speaking of the Rich twist, this comes with what’s perhaps an even bigger reveal: that Pennywise can see the future. Technically, because It’s true Deadlights form originates outside of “our” universe, the entity has never been bound to the normal laws of it, but this is the most direct explanation of it we’ve ever had: “Tomorrow. Yesterday. It’s all the same for little Pennywise.”

Although this is something of a change to King’s work, there is some precedent for this. When Beverly looks into the Deadlights in IT, she has a vision of the Losers as adults fighting Pennywise again. However, Welcome to Derry is taking things further, as it suggests the future is not set in stone, and that Pennywise can change the past to impact it.

He even questions whether his death was actually his birth, which could leave some potential wiggle room for the character to return if they ever wanted to make IT: Chapter Three. But it also means that, in Seasons 2 and 3, we’re going to have a Pennywise who is aware of the events of Season 1, and looking at ways to avoid them happening. Which… opens itself up to a lot of complications, so it’s a bold strategy, and we’ll have to wait to see if it pays off.

What Happens to Welcome to Derry’s Losers After Season 1?

Marge, Will, Rich, and Lilly in IT Welcome to Derry
Image via HBO

IT: Welcome to Derry Season 2 will be set in 1935, so there’s a good chance we’ve seen the last of the show’s main characters, especially the children. With Pennywise gone, while there’ll still be some lingering trauma for them to work through, there’s not an obvious story reason to bring them back. Still, things at least end on a hopeful note, with Ronnie leaving town (and maybe remember, maybe forget), and Lilly in a much better place after going through so much.

We do know, though, what happens to Will Hanlon and Marge Truman. As discussed earlier, Marge will become the mother of Richie Tozier: she’s a minor character in King’s work, but it does reveal some things about her. While she’s similar to Richie as a child, it’s a different story as an adult, where she finds him harder to relate to, and the family struggles for money, which does make for a slightly sadder future after Welcome to Derry.

There is a bigger tragedy for Will, who is the father of Losers Club member Mike: he and his wife, Jessica, both die in a housefire, which is even more grim after what happened at The Black Spot, and the fact the Hanlons came so close to leaving Derry. There’s is now a generational story of tragedy, and part of it was almost avoided.

How Dick Hallorann’s Ending Sets Up The Shining

Dick Hallorann in IT Welcome to Derry Season 1 Episode 8
Image via HBO

It’s not just IT that Welcome to Derry connects to, as it also sets up The Shining. Dick Hallorann decides to leave Derry at the end of Season 1, which is certainly an understandable choice, and reveals that he’s going to London to work in a restaurant at a hotel one of his friends has opened. While he’s not quite on his way to the Overlook Hotel, this puts him on the career path that will lead him there, because he’s the chef in The Shining. There’s even a not-so-subtle nod towards this in the finale, as he says: “How much trouble can a hotel be?” Oh, Dick.

The Real Meaning Of IT: Welcome to Derry’s Ending

Lilly, Ronnie, and MArge looking at missing posters in IT Welcome to Derry

IT: Welcome to Derry‘s finale reflects the core themes and ideas of the entire season, and of the IT movies (and book) as well. In particular, the defeat of Pennywise at the hands of Lilly, Marge, Will, Ronnie, and Rich is, like the Losers, about the power of friendship, and how working together, and truly being there for someone, not only makes them stronger, but makes you stronger as well. Fear is a powerful weapon, but the belief that you’re not alone is one of the greatest ways to combat it.

It also speaks to the trauma that persists throughout the generations of Derry, from 1908 – we saw General Shaw, who once saw Pennywise as a young boy, shocked to discover the entity again – through to Mrs. Kersh and Beverly in 1988 at the very end. But it also shows how those cycles can be overcome and broken, and how people can begin to heal. Derry, not Pennywise, may be the real monster in a sense, because of its ingrained prejudices, but there is also the chance to find a sense of community, as the Hanlons do, that can allow them to be part of something bigger, and to continue facing that adverity even when it’s the more difficult choice.

What We Know About IT: Welcome to Derry Season 2

Bradley Gang massacre in Derry newspaper in IT

At the time of writing, IT: Welcome to Derry Season 2 has not been confirmed by HBO, but a renewal does seem likely. As well as good reviews and word-of-mouth, the show has been a major hit: the premiere was the third biggest in HBO Max history, behind The Last of Us and House of the Dragon. That puts it in very good company, and while nothing is ever certain, it’d be a major surprise if it wasn’t picked up for more, especially with so many plans in place.

Welcome to Derry Season 2, if it does happen, will primarily be set in 1935. We already saw a little bit of this in Season 1, with the flashbacks to a younger Ingrid Kersh, who could appear once again. The major event, though, will be the Bradley Gang massacre. Like the burning of The Black Spot, this is one of the major events in Derry history that’s revealed in Mike Hanlon’s interludes in the book, and will likely serve a similar function in the story. Season 2 would presumably have a mostly new cast, but it’s probably safe to assume Bill Skarsgård returning as Pennywise.

All episodes of IT: Welcome to Derry Season 1 are now available to stream on HBO Max.

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