Who’s the Worst Villain on ‘It: Welcome to Derry’? Take Your Pick

Kids being menaced by supernatural monsters is nothing new in horror, but it sure does seem to be happening a lot lately. Most recently, we’ve gotten reacquainted with Stranger Things‘ Vecna, now featuring military backup he didn’t ask for but is certainly using to his advantage.

But now, just a little over a week past the long-anticipated arrival of Stranger Things season five, It: Welcome to Derry has dropped an episode that declares its villains the best at being the worst. And if you think that plural is a mistake—that Pennywise the Dancing Clown, the guy who cackled through both Andy Muschietti movies, is the only game in town—think again. The show has been carefully laying the foundation for its big climax all this time, and the jaw-dropping events of episode seven deliver, deliver again, and then throw one last big twist in your face, just for funsies.

So, with that in mind, let’s break down the range of monsters featured in It: Welcome to Derry. We definitely can’t rank them because they’re all awful, but they’re also all awful in different ways.

Ingrid Kersh

Ingrid (Madeleine Stowe) got major backstory in last week’s “In the Name of the Father,†and Welcome to Derry went deeper this week, returning to 1908 to show us Ingrid’s life with her father, Bob Gray, the original Pennywise the Dancing Clown. He was the actual human beneath the make-up, before the entity in Derry’s woods got ahold of him.

We don’t see exactly what happens when he gets “taken,†and we don’t learn exactly why the entity decided Pennywise would be its ideal form. But we get some hints. During a performance at that same dinky carnival we saw back in episode three—the one with the li’l Shaw and Rose flashback—we notice an emotionless child gazing at the clown from a distance, watching the clown’s effect on the kid-filled audience. Later, the boy appears during Bob’s smoke break (wig off, greasepaint smeared) and asks for help. Bob’s reluctant (he literally tells the kid, “Scram!â€), but he eventually agrees to go into the forest.

In just a few scenes, Bill Skarsgård gets to explore new facets of his signature character, and he wastes not a second of the opportunity. (He also gets to reverse-engineer his scary Pennywise voice into something more earthbound; much like Bob himself, it’s got a forced chipper quality that almost masks all the melancholy pulsing underneath.)

Bob clearly mourns his glory days working for a real, big-top circus—where bratty kids don’t run onstage at the end of your act and rip the wig off your head. But he’s kind to Ingrid and supports her dream of performing, praising her efforts when she shows off her make-up, costume, and wig. He even suggests she use the stage name “Periwinkle,†as her mother once did.

The adult Ingrid is still clinging to the memory of that father-daughter bond with all her might; over 50 years later, she’s still seeking Daddy’s approval. We learned as much in last week’s episode. But in episode seven, we learn how twisted it gets. As you’ll recall, she sought the help of Charlotte Hanlon (Taylour Paige) to bring Hank Grogan (Stephen Rider) to the Black Spot. At the time, viewers figured it was because Ingrid wanted her secret lover to stay safe after his escape from the prison bus.

But no. She wanted to see “Papa†again. This time, her method of doing that ends up involving her husband, Stan, and his racist cronies.

“I knew they would come if they thought he was here,†she tells a somewhat befuddled Pennywise, describing her plan to draw him out by using Hank as bait. “And there would be blood and pain and fear, and I knew that you wouldn’t be able to resist it.â€

So it’s now crystal clear: all this time, Ingrid has been plotting with one single goal in mind. Her kindness to Lilly? Her relationship with Hank? Dressing up in her old Periwinkle outfit? It’s all been part of her diabolical scheme to see her father again.

It’s a very short reunion, as it turns out. Pennywise, who’s quite finished with this weepy woman, announces it’s time for another 27-year snooze—and when she pushes back, his cruel reaction is enough to make her see at last that this Pennywise is not her father.

It doesn’t end well for Ingrid—those deadlights will knock you out—and she’s fully an instrument of the entity now. We can assume this is how Beverly is able to meet her an improbable number of decades later in It: Chapter Two, by which time she’s simply become another one of Pennywise’s nightmarish forms.

Clint Bowers and his posse

Stephen King fans have known the burning of the Black Spot was coming, and episode seven delivered with all the flames, terror, agony, and awfulness you’d expect.

Recently relieved of his job as Derry’s top cop, a salty Clint Bowers (Peter Outerbridge, an actor who Expanse fans already love to hate) rounds up all his like-minded pals, including Stan Kersh. With their faces covered in dime-store Halloween masks, the men pull up to the Black Spot and barge in with guns, demanding the patrons—who are mostly Black servicemen, with civilians and a few terrified teens sprinkled in—hand over Hank Grogan.

When the Black Spot patrons refuse, brandishing their own weapons, Bowers and company retreat. But then we hear them barricading the door before they set the place on fire and start shooting through the walls. The sequence goes on seemingly forever as extreme panic sets in. Dick Hallorann (Chris Chalk) is able to break through the floorboards and get Hank, his daughter Ronnie (Amanda Christine), and Will Hanlon (Blake Cameron James) out safely. Rich (Arian S. Cartaya) heroically saves Marge (Matilda Lawler) at the cost of his own life. And while Hallorann also manages to escape the inferno, he’s now being aggressively haunted by restless spirits. Even our old pal Pennywise pops up to taunt him.

It’s an unimaginable tragedy, nearly two dozen killed, and we hear a radio news report brushing it off as “an electrical fire,†using an outdated racial term while describing the place as an “illegal speakeasy.†In the aftermath, Will’s mother, Charlotte, puts the blame where it belongs: “It wasn’t that thing that lit the fire last night,†she says. “This town is the monster.â€

General Shaw

General Shaw (James Remar) has been a tricky character from the start. The top man at Derry Air Force Base is vehemently patriotic. He absolutely won’t tolerate racism in the ranks. He has history in Derry—he was Rose’s (Kimberly Guerrero) childhood sweetheart—and had an uncomfortably close encounter with the monster that haunts its woods. He’s one of few to understand its true power and has somehow gotten the military on board with his unhinged scheme to trap and weaponize the entity.

But the mission that Major Leroy Hanlon (Jovan Adepo) and Hallorann have been risking their lives to pursue? That caused the death of Captain Russo (Rudy Mancuso)? That Rose, on behalf of the Indigenous community, tried to talk Shaw out of? It’s not what we thought it was. All this time, viewers have been led to believe that Shaw is trying to ensnare the entity for purposes relating to the Cold War. But we’ve all misunderstood which “war†is in his sights.

The last five minutes of episode seven peeled back the layers on Shaw, to the point that Hanlon rightfully yells, “You are fuckin’ insane!†at his superior officer once he learns the truth.

Hallorann helps Shaw’s men find one of the “pillars,†carefully buried and protected by the local Indigenous tribe, that’s been keeping the entity contained within Derry for centuries. The understanding was, the soldiers would use their knowledge of the pillar’s location to start making the entity’s prison smaller, eventually pinpointing its exact location.

But Shaw instead orders the pillar, a shard of the star that encased the alien when it crashed to Earth, brought to the base. Turns out he plans to melt it down, study it, and use its fear-generating powers against the American people.

Yep. “The greatest threat to this country is not from without,†he tells an incredulous Hanlon. “It’s from within. Americans are at each other’s throats… the country is fracturing.†He’s trying to prevent another civil war, Shaw explains, and “the only thing that really makes people listen is fear.â€

Listen—or obey? And at what cost? This thing feasts on children, after all! Shaw doesn’t quite say “Make America Derry Again,†but… yeah. He is determined to see this through. And he’s not going to let anyone spoil his grand plan. Unless perhaps a certain newly liberated clown will crash the party in next week’s season finale?

Pennywise the Dancing Clown

Let’s not count out the original fiend in all of this. The entity can’t be controlled. Rose knows this. Hanlon and Hallorann know this. We know this. Everyone except Shaw and his minions has accepted this as a fact.

When Shaw ordered the pillar removed from Derry’s soil, he “left the cage door open,†as Hanlon correctly puts it. Shaw was further emboldened when Hallorann admitted he couldn’t psychically sense the creature anymore and figured its next sleep cycle had begun.

But Shaw didn’t count on its eyes eagerly popping open when it realized its new freedom. A little more time to kill, it seems!

Eventually, Pennywise is going to need his naptime. He’s got to be well-rested ahead of meeting the Losers Club in 1989. But there’s still one more episode of It: Welcome to Derry to go—and some scores to settle before we see this season through.

The It: Welcome to Derry finale arrives December 14 on HBO and HBO Max.

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