Even By Stephen King Standards, It: Welcome To Derry Season 2 Is Set To Be Bleak

While Stephen King is hardly known for his uplifting stories, the second season of HBO Max’s IT: Welcome to Derry will still be unusually bleak even compared to the author’s usual output. A viewer who has only ever seen The Shawshank Redemption or The Haunting of Hill House director Mike Flanagan’s underrated 2025 novella adaptation The Life of Chuck could be forgiven for assuming that American author Stephen King is known for his life-affirming character studies.

However, anyone familiar with the writer’s most famous works, from It to Carrie to The Shining, will know better. As the pre-eminent voice in mainstream post-war American horror fiction, King has penned some of the bleakest and most brutal bestsellers of the last five decades. One particularly infamous King story, the soon-to-be-rebooted The Mist, boasts the dubious accolade of having one of the bleakest endings in movie history.

As such, it might seem surprising that season 2 of HBO Max’s It prequel It: Welcome To Derry will somehow be even more dour and downbeat than its predecessor. Since the It movies take place in the ‘80s and 2019, viewers always knew that It: Welcome To Derry’s prequel story couldn’t end with Pennywise the Dancing Clown’s permanent defeat. However, what audience members might not have anticipated was just how much the first season of the prequel would lean into its predetermined tonal darkness.

It: Welcome To Derry Season 2's Timeline Means The Story Is Set In The Depression Era

Ending its pilot episode with a jaw-dropping sequence that killed off almost every named character, most of them children, It: Welcome To Derry wasted no time proving to viewers that the show was not messing around. The series was astoundingly bleak but remained compelling viewing nonetheless, and season 1’s story culminated with a racially motivated massacre that was almost unwatchable-y horrific, but vital to the backstory of the titular town.

After this disturbing opening salvo, it is hard to imagine how It: Welcome To Derry season 2 could hope to outdo its predecessor. However, this is where the saddest time-twisting series since Netflix’s sci-fi masterpiece Dark reveals the secret up its sleeve. Since Pennywise the Dancing Clown only re-emerges once every three decades (approximately every 17 years, to be more specific), season 2 will be set in the 30s.

More specifically, It: Welcome To Derry season 2’s story takes place bang in the middle of the Great Depression. According to director Andy Muschietti’s conversation with Variety, 1935 Derry will be defined by the same economic devastation that shredded the social fabric of the rest of the nation throughout the decade.

How Derry's Status In Season 2 Will Benefit Pennywise

Per Muschietti, "Everybody’s trying to get by and survive the circumstances. They are gonna do crazy things. And of course, the social, cultural, horrible things that were happening in the era, too… Derry is almost a graveyard. It’s a carcass of something because people are depleted, poor, tired, jobless, homeless. The kids don’t have a suburban, comforting life. They’re in a very different situation. Some of them are orphans or runaways, and so the environment is pretty bleak.”

Of course, anyone familiar with the modus operandi of Derry’s resident monster Pennywise the Dancing Clown will have alarm bells going off in their heads after reading that description. After all, Pennywise feeds on negative emotions like fear, greed, pain, sadness, heartbreak, and anger, so he will enjoy a veritable all-you-can-eat buffet of these bad vibes in 1935 Derry.

The more Pennywise feeds, the stronger he becomes, meaning the clown can expect to gain a stranglehold over Derry in 1935. The real question, then, is how the show will keep viewers invested in a story that features a superpowered monster who is guaranteed to survive and a group of starving, desperate, and understandably depressed protagonists. While It: Welcome To Derry season 2’s plot clearly won’t be relying on upbeat fun to keep fans coming back, the fact that season 1 managed to keep its extremely grim plot compelling bodes well for this sophomore effort.