Summary
It: Welcome to Derry finally lets Pennywise off the leash in “29 Neibolt Street”, albeit only briefly, but he’s the centrepiece of an hour with plenty of revelations and horrors elsewhere.
It: Welcome to Derry has held off on leveraging the iconic smirking visage of Bill Skarsgård’s bulbous-headed Pennywise the Clown. It wasn’t until the third episode that we even got a glimpse, and it’s only here in Episode 5, “29 Neibolt Street”, that he shows up in full regalia. Even then, the appearance is brief, which stands to reason, because the “Entity” hiding under Derry is many things to many people, and this episode, just over the halfway point of the season, hinges on a whole host of impostors venturing deep into Pennywise’s lair to become victims of their own worst fears.
These intruders include a coterie of U.S. Army personnel and, of course, this show’s version of the Losers Club, which picks up two new members. You probably don’t need me to tell you which group fares better, though given how Welcome to Derry has treated its child characters thus far, maybe you do.
One of those new additions is unexpectedly Marge. It turns out that even though everyone else widely suspects that Lilly was guilty of blinding her with a chisel, Marge knows better. She understands that her nasty goggle-eyed experience was a consequence of being targeted by Pennywise, which means that Lilly was telling the truth all along. Suddenly, the Patty Cakes don’t seem too important, and Marge is adamant about clearing Lilly’s name. This doesn’t make a great deal of sense, since it’s repeatedly clarified that nobody actually believes Marge, but Lilly is still allowed to chill at her hospital bedside either way. Let’s not think too much about that.
The other new arrival is Matty, whom the kids find squatting in a tent in their rooftop hideaway. He’s not looking too good, and that’s putting it mildly, but I suppose that’s to be expected after spending weeks in the sewers being tormented by Pennywise. So he claims, anyway. I didn’t for a moment think this was the real Matty, but the kids don’t really entertain the possibility that he shouldn’t be trusted. And since he claims that Phil might still be alive in the tunnels, they bravely resolve to rescue him, especially since he can exonerate Ronnie’s father (“Matty” is, conveniently, totally unwilling to return home or go to the police.)
Obviousness of the twist this is setting up aside, it’s a riot in execution. You wouldn’t think a bunch of kids getting high on stolen Valium and then being tormented in the sewers by a cosmic demon that feeds on fear would be especially enjoyable fare, but you’d be wrong, and It: Welcome to Derry Episode 5 delights in the surreality of the whole set-piece. It also delights in the reveal that Matty is really Pennywise himself, giving Skarsgård his big moment in makeup and costume. It’s all tons of fun, even if it doesn’t amount to a great deal yet, since the kids are able to escape, and a separated Lilly is able to freeze Pennywise in place using the crystal shard that Taniel brought with him. But this requires some more explanation.

Clara Stack in It: Welcome to Derry | Image via WarnerMedia
“29 Neibolt Street” is the first episode to properly unite the kids and the adults on the same narrative track, albeit without knowledge of each other. The U.S. military makes its own way there. After using Dick Halloran to scrape Pennywise’s backstory from Taniel’s mind, General Shaw now feels ready to make a move on the Entity, cornering it in the tunnels beneath the house of Neibolt Street and capturing it for use as a potential weapon to end the Cold War.
Leroy isn’t exactly thrilled to hear this, especially since it confirms that Shaw knew of the dangers and still allowed Leroy to move his entire family into town, but his counterpoint is that they were supposed to stay on the base, where they’d be more protected (somehow). Even after Charlotte and Will are moved onto the base, it isn’t as if they stay out of trouble. Will is able to sneak out to rendezvous with his friends, and Charlotte is keeping her eye on Ronnie’s father, whose prison transport is attacked on the way to Shawshank, allowing Hank to become a fugitive. At this point, it might be the best thing for him. We also learn that his paramour is Ingrid, the only woman in town that Lilly trusts, and Charlotte might be the only person they can turn to.
Meanwhile, Leroy and several other soldiers take Taniel, armed with the crystal shard given to him by Rose, into the tunnels. The plan is to “secure” Pennywise, which is very funny in principle, and I think the whole thing, despite being full of very obvious horrors, is being played for laughs deliberately. The military is being made fun of. For all the posturing, Uncle Sam’s finest fall prey to Pennywise’s machinations in record time, despite being forewarned that their fears will be used against them. The point being made, I think, is that this isn’t an enemy you can shoot. It’s a threat that burrows into the deepest recesses of your psyche.
Halloran pays the price for this more than the others, who generally just get confused and shoot each other and run straight into Pennywise. But Halloran is plunged into a deep repressed memory of his grandparents; his grandmother, also blessed with the Shine and thus able to communicate with him telepathically, trying to protect him from his abusive grandfather, who forces him to open a lockbox of some vague and unspecified evil. It: Welcome to Derry does a great job here of blurring the lines between memory and reality, between the very real evil of Dick’s past and the cosmic version Pennywise is creating in his present.
Dick survives the encounter, but the fact that he can still see those who didn’t suggests that he’ll never be quite free of the dead.
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