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Stephen King’s work is full of iconic horror villains, and Pennywise the Clown is perhaps his most recognizable. The pasty, red-haired freak has been terrorizing millions since King first wrote his book It back in 1986. Since then, It has spawned a miniseries, two movies, and an upcoming HBO series, It: Welcome to Derry. In case you need a refresher, King’s book tells the story of a group of kids, nicknamed The Losers Club, in Derry, Maine, who are hunted by a shapeshifting clown-like being called Pennywise. In the novel, the story switches back and forth between The Losers Club when they were children and their adult selves as they try to grapple with the trauma of their pasts. If you’re in the mood to get the pants scared off of you, look no further than It. Without much further ado, let’s get into how to watch It and its spinoffs in release and chronological order. 

How to watch It and the Welcome to Derry spinoff in release order 

Luckily, if you want to watch all of the It adaptations and spinoffs, you’re working with a pretty small list. You would start with the original, 2 episode miniseries from 1990 simply entitled “It.” It (haha) features Tim Curry in the role of Pennywise, and as any 90s can tell you, Curry’s portrayal of the character lingered in pop culture long after the miniseries’s release. From there, you would go to the 2017 It film, then continue on to It: Chapter Two, which adapts the parts of King’s novel where the Losers are adults. And finally, you would end (for now) with It: Welcome to Derry. 

• It (1990 miniseries)
• It (2017)
• It: Chapter Two (2019)
• It: Welcome to Derry (2025)

How to watch It and the Welcome to Derry spinoff in chronological order

If you want to watch It in chronological order, then your starting and ending points are simple. It: Welcome to Derry is a prequel series to the events of the 2017 It film. If you don’t remember, It (2017) is set in the year 1988. However, it should also be noted that in King’s original novel, the scenes with all of the Losers as children takes place in the late 1950s. Likewise, in the 1990 It miniseries, the Losers’ childhood scenes take place in 1960. So if you want to build a sense of chronology with the It films and spinoffs, you’re going to have to ignore the 1990 miniseries, because it is simply outnumbered by the succeeding It adaptations that have their own timeline. 

• It: Welcome to Derry - the '60s
• It (2017) - 1988
• It: Chapter Two - 2016

Just for posterity’s sake, I’ll also note the timespan for the 1990 It miniseries here. 

• It (1990 miniseries) - 1960 and 1990

What is the point of It by Stephen King?

I think the significance of It depends on the person, because fear is a personal experience. But part of what has made It such an enduring story is its exploration of childhood trauma and the lifelong bonds that trauma forges between people. For better or for worse, I think a lot of us can relate to the Losers and their quest to defeat an evil from their childhoods. In Stephen King fashion, his story is an unflinching look at the horrible things that can happen to people in childhood, and perhaps that provides a lot of catharsis for folks. 

What is Pennywise’s weakness in the movie It?

Like so many of us, Pennywise is vulnerable to the audacity of middle schoolers. His moments of weakness in the It films are when the Losers insult him (like when Richie calls Pennywise’s lair a “crackhead house”) or when they tell him that they’re not afraid of him. This is why Beverly was unable to be killed by him, because she wasn’t afraid of him. 

Did Stephen King ever act?

Yes! I have been waiting to answer this question for twenty years. Stephen King has made lots of cameos in adaptations of his own work and beyond. He wrote the 1982 Creepshow movie, where he delivers a delightfully campy performance as a farmer who discovers a meteor. In 1987, King appeared in Creepshow 2, this time making a cameo as a truck driver. Sometimes I feel like I’m the only one who remembers this, but Stephen King also made a brief appearance in the 2005 romantic comedy Fever Pitch, where he can be seen throwing the first pitch at a Red Sox game at Fenway Park, in a perfect encapsulation of New England culture. 

Can Pennywise only eat you if you’re scared?

Yes, that’s correct. In Dune, fear may be the mind killer, but in It, fear is the everything killer. The best way you can armor yourself against Pennywise is to be afraid of him and his antics. 

What was Pennywise before he was a clown?

Pennywise is an alien entity from space, who crash landed on Earth millions of years ago and was reawakened at the time of human civilization. The creature has been terrorizing residents of the Derry-area ever since. 

In the immortal words of Danny Elfman, "Life's no fun without a good scare." We couldn't agree more, which is why we think you should check out horror aficionado Greg Silber's list of the best horror movies of all time. Or, if you've already seen those classics, check out our list of the most underrated horror movies from the past couple years. And if you've already seen all of those, Let us tell you what to look forward to (or dread) in Popverse's list of upcoming horror movies.