‘IT’ Watch Order: Guide to Every Pennywise Movie & Show

If there’s a horror movie series that has always been a favorite among fans, it’s Stephen King’s IT franchise as it allows us to see clowns in a different way due to the fact that the storyline features a monstrous being they call “IT,” which likes to take on the form of a clown. In that regard, many people have become traumatized by the sight of a clown due to the man-eating face-painted entity that has made Stephen King’s book a household name.

Due to the massive popularity of the recent IT movies and because we live in a time when people now have on-the-go access to their favorite movies and series in the streaming era, the demand for a storyline that’s based on the IT universe only keeps on getting bigger. That’s why Welcome to Derry is set to be the latest addition to this cinematic world. So, with that said, let’s look at the IT watch order.

How Many IT Movies and Series Are There?

Stephen King is often considered the modern-day master of horror novels, as he has created a lot of masterpieces that dwell on some of the most horrifying tales ever written. His stories aren’t always about ghosts and demons, as they focus more on horrifying creatures that are beyond our imagination or, at the very least, close to home. One such masterpiece is IT, which stands as one of the most popular Stephen King novels of all time.

What makes IT so successful is that it reimagines how we see clowns. While clowns have always been meant to make kids feel happy and jolly due to their colorful faces and personalities, IT changed everything with the introduction of Pennywise the Dancing Clown, who is actually an extra-dimensional being that took the form of a clown to get his hands on kids and use their fear as nourishment.

Due to its popularity, IT was adapted into several live-action versions that have become quite popular in their own right. The best part is that these live-action works span generations due to the fact that IT earned a remake more than 30 years since the novel was published and 27 years after the first live-action adaptation. So, how many IT movies and series are there?

There are only two IT movies. Meanwhile, there are three IT series. The first adaptation of IT was through a TV-only mini-series that was split into chapters that allowed us to see how the kids of Derry grew from the early part of the storyline. Then, in 2017 and 2019, the IT movies were released as remakes of the original IT mini-series released during the 90s. 

There’s also the fact that HBO Max has just recently ordered an IT series that will be streaming on HBO’s service provider sometime in the near future. This series is called Welcome to Derry, as it will be the next entry to the popular IT franchise. Welcome to Derry adds to the total, as we have five live-action adaptations of IT.

IT Watch Order:

1. Welcome to Derry (TBA)

Welcome to Derry has just been recently announced as a series that will be released on HBO Max sometime soon. However, we don’t know when it will be released as there is no timetable for the entire project. It may see a 2024 or 2025 release date, depending on how fast the production will be.

At this point, we don’t know much about Welcome to Derry except that it will take place in the same universe as the other IT movies and series. But we can speculate that this series will be a prequel to the original IT storyline, especially because it already concluded with Pennywise’s defeat at the end. Welcome to Derry might focus on a story that takes place before the events of IT, as we do know that Pennywise has been around for a very long time and victimizes kids every 27 or so years.

2. IT (1990)

It was in 1990 that the first IT adaptation was released as this was a TV-only production that was split into different parts and chapters to deliver a series that scared a lot of people during the 90s and got them to see just how scary clowns can be. Helmed by the fantastic performance of Tim Curry as the original version of Pennywise, the 1990 version of IT was a great start to what is an extremely entertaining 90s production that didn’t have the same access to technology that the recent IT movies have.

3. IT (2017)

Around 27 years after the first IT production was released, Stephen King’s classic work was given new life in the form of the 2017 remake of the book. Helmed by a new generation of kids that ended up experiencing breakout roles, the IT remake had the luxury of using modern—technology to deliver a gory and scarier ride that’s full of special effects.

This time, Pennywise was given life by the masterful performance of Bill Skarsgård. While Curry’s Pennywise was more like a mad serial killer, Skarsgård’s version seemed more monstrous due to its out-of-this-world appearance and monstrous powers. As such, it is a wonderful yet scary reimagining of Pennywise in a movie that proves to be just as horrific as the original version.

4. IT Part 2 (1990)

Again, the first IT was split into parts that allowed us to see the protagonists in their younger and adult forms. Part 2 was a bit weaker than when the characters were still kids, but it could still deliver a great mix of playfulness and horror. This storyline revolves around how the Derry Loser’s Club, now adults, are finally looking to end the nightmare plaguing them ever since they were little. 

5. IT Chapter Two (2019)

After the Losers Club seemingly defeated Pennywise in the first movie, the Dancing Clown returned in Chapter Two as he is now looking to finish what he started decades ago. This time, the Losers Club are now adults with different lives compared to when they were kids, as they are now looking to find a way to settle the score with Pennywise once and for all.

The only problem here is that, as adults, they now have more fears than when they were still kids. Pennywise is now more powerful than ever and can now feed on the adult fears of the Losers Club. Still, the protagonists are now trying to end Pennywise for good, as this shows how the storyline concludes with the defeat of this extra-dimensional being.