When does Pennywise show up on ‘IT: Welcome to Derry?’: Episode 1’s clues collected

Brace yourself, Stephen King fans, because the story of Pennywise the Dancing Clown is expanding like a bright red balloon. 

With IT: Welcome to Derry, Andy Muschietti and Barbara Muschietti (the sibling filmmaking team behind IT and IT: Chapter Two) return to the deeply doomed Maine town where the Losers Club battled for their lives twice in 27 years. However, Bill, Beverly, Eddie, Mike, Richie, Stan, and Ben aren’t in this new series. Set in 1962, this is a prequel playing out 27 years before they ever tangled with Pennywise. But you better believe the clown is back — just not quite as you might expect. 

Pennywise is all over the advertising for IT: Welcome to Derry. It is known that Bill Skarsgård is reprising the role from the films and serving as an executive producer on the series. But there’s no clown in the premiere episode. However, there are callbacks to the IT movies that hint at Pennywise’s resurrection. So, let’s dig into them. 

Be warned: Major spoilers ahead. 

Where does Pennywise appear in episode 1 of IT: Welcome to Derry? 

Bill Skarsgård plays Pennywise the Dancing Clown in “Welcome to Derry.”
Credit: Brooke Palmer / HBO

The first signs are with poor Matty (Miles Ekhardt), who’s run away from home and only found trouble (trouble, trouble). Looking to get far from Derry, he hitches a ride with a family of four. But things swiftly turn scary with a snarling sister snacking on bloody liver and an annoying little brother spelling increasingly ominous words. 

It’s this brother that gives us our first hint of Pennywise’s presence. First, his eyes go wonky, transforming from those of a little boy to those of a deranged extraterrestrial clown. Then, his buck teeth remind us of Pennywise’s signature, sinister smile. Next, a new arrival gives us a more impressive display of Pennywise’s power. 

The baby with bat wings has big Pennywise energy. 

Miles Ekhardt plays Matty in “IT: Welcome to Derry.”
Credit: Brooke Palmer / HBO

The mother of this malevolent family births a two-headed monster baby with bat wings. And while that’s all kinds of wild, it has visual ties to both movies. First off, the Muschiettis’ reimagining of Pennywise veered away hard from the Tim Curry version, which was more of a classical Bozo-styled clown. The Muschiettis opted for a Victorian flair in costume and a Kewpie-doll head, characterized by a massive forehead reminiscent of a baby doll. So, that double noggin should remind viewers of Skarsgård’s Pennywise, even before this grisly cold open sweeps us into the sewer, chasing after Matty’s dropped pacifier. 

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Beyond the big-head design, the baby is reminiscent of another Pennywise precursor. A similar unholy critter sprouted out of a fortune cookie and crawled about the table at the Chinese restaurant in IT: Chapter Two. It was a baby-doll-headed spider of sorts, while another fortune cookie busted out a bat wing. So, long before the Losers Club was tormented with this nightmare fuel, the Derry kids of 1962 were witnessing it with fresh horror. 

IT: Welcome to Derry has echoes of Georgie’s disappearance. 

Jack Molloy Legault and Mikkal Karim-Fidler play Teddy and Phil in “IT: Welcome to Derry.”
Credit: Brooke Palmer / HBO

When Matty goes missing, his classmates Teddy and Phil (Mikkal Karim-Fidler and Jack Molloy Legault), bicker about what could have become of him. “They never found a body,” one argues, suggesting he’s not dead but run away.

However, that was true for Bill’s little brother, Georgie Denbrough, too. He went missing but no body was found. That’s what led to Bill’s obsession of searching the sewers.

Another Georgie callback hits before the end of episode one. But let’s take these in chronological order, shall we? 

Voices from the drain menace traumatized kids. 

Clara Stack plays Lilly in “IT: Welcome to Derry.”
Credit: Brooke Palmer / HBO

Poor “Loony” Lilly (Clara Stack) already has enough to deal with, like the horrific accidental death of her father and the vicious Pattycakes mocking her about it with a pickle prank. Then, while in the bathroom all alone, she hears the voice of the missing Matty coming from the tub’s drain. 

Saying “We’ve got trouble” in a sing-songy voice, he’s harkening back to the movie he watched at the theater before his fateful hitchhiking. “Ya Got Trouble” from The Music Man takes on an ominous connotation as Matty sings it to signal he’s been snatched (and maybe killed) by Pennywise.

Of course, Lilly doesn’t know anything about this homicidal clown yet. However, this scene evokes the moment when Beverly Marsh in IT heard the voices of three of Pennywise’s victims calling to her from the bathroom sink. Where Bev got attacked by surging hair and a flood of blood, Lilly sees two severed, bloody fingers wiggle their way up to her. But Lilly has a tougher time convincing her peers to believe what she saw than Bev did. Phil and Teddy need more to believe, and they’ll get it.

Matty reappears with a Pennywise makeover. 

Miles Ekhardt plays Matty in “IT: Welcome to Derry.”
Credit: Brooke Palmer / HBO

To better understand Matty’s message, Lilly, Teddy, Phil, and Ronnie (Amanda Christine) return to the theater to watch The Music Man for clues. To their shock, they find Matty there. But not in the theater. He’s on the screen, where he curses them out for letting him down. Then, he gets a Pennywise makeover, his smile distorting with buck teeth before he launches the monster baby from the screen and into the theater.

Pennywise is here, and he’s shapeshifting to terrorize these children of Derry. 

One more Georgie callback, and we can’t shake it. 

Jack Molloy Legault and Matilda Legault play Phil and Susie in “IT: Welcome to Derry.”
Credit: Brooke Palmer/HBO

Little Susie (Matilda Legault) would have been better off left at the library. Phil’s little sister is too young to have any idea what she’s in for when she tags along to the theater. Like Georgie, she’ll be the younger sibling who loses an arm from a Pennywise attack.

Trying to climb to safety under the theater seats, pig-tailed Susie reaches to Lilly for help. And while Lilly grips her hand, it won’t save Susie from the many-fanged maw of the monster baby. It lunges and chomps deep into Susie’s exposed arm. So much so that when Lilly runs out of the theater, she’s still got Susie’s hand in hers, dripping blood from its severed elbow. 

While Pennywise doesn’t appear in full in episode 1, he’s left plenty of horrifying hints that he’s rising in Derry. And he’s hungry.

After the absolutely jaw-dropping mayhem of this premiere episode, what could possible come next? 

Tune in next Sunday to HBO and HBO Max find out. And keep up with Mashable, as we’re breaking down every gory detail of Welcome to Derry.