Every Movie In Disney’s Halloweentown Franchise, Ranked

Disney has always done a good job of releasing great Halloween movies for people who don’t like horror and, in fact, even has an entire series comprising that particular flavor of spooky season cinema. In 1998, the Disney Channel original movie, “Halloweentown,” first aired, becoming an instant classic for families looking for a lighter, more kid-friendly alternative to the scary, bloody, violent fare that typically dominates the season. And even though it would’ve likely remained a staple for fans for many years to come even without any sequels, there have nevertheless been four entries in the “Halloweentown” franchise thus far.

The main connective thread between all four films, apart from the titular magical town, is that they all follow a witch named Marnie Piper (Kimberly J. Brown or Sara Paxton, depending on the film), her siblings, and her grandmother — cousin of fabled magician Merlin — Agatha “Aggie” Cromwell (Debbie Reynolds). The first movie centers around the initial journey to Halloweentown and Marnie discovering that she’s a witch. The second is your typical “and now here’s a new bad guy to threaten everyone” sequel premise, while the third and fourth installments each take things in their own unique directions.

Did the bold new swings in the latter half of the series make for better films? Or did the “Halloweentown” series get worse the further it got from its original foundation, leaving the earliest installments as the franchise’s best? Read on to see how we rank the four films.

Since the third “Halloweentown” movie focused on Marnie in high school, it was a natural evolution to have the next installment in the series follow her to college. And so we have “Return to Halloweentown,” where Marnie decides to attend the magical Witch University rather than going to a regular college as her mother (Judith Hoag) had hoped. Needless to say, the movie isn’t just about Marnie having a fun, incident-free journey through higher education. There are sinister things going on within the institution, dangers that Marnie has to aid in sussing out and putting a stop to.

The fact that Marnie was recast for the first time in the history of the series — played here by Sara Paxton rather than Kimberly J. Brown, who portrayed the franchise’s hero in the three previous installments — was a major sore spot for longtime fans. The revelation that Brown was apparently available and fully willing to do the part but was recast anyway only caused further disdain towards the film.

All that aside, it’s still the weakest entry in the series, thanks in large part to an overly convoluted time-travel plot. The film veers more towards “Harry Potter” fantasy territory and away from light horror and gives very little screen time to Aggie in what ended up being one of Debbie Reynolds’s final roles. Fans might not have outright hated “Return to Halloweentown” if Disney had brought back Brown, but they still would’ve liked it the least out of all the entries in the franchise.

After releasing two fairly similar entries in “Halloweentown” and “Halloweentown II: Kalabar’s Revenge,” a creative shift was needed in order to justify a third entry, something that would make sure it wasn’t simply more of the same only with a different new big bad. And so it was decided that, with Marnie now old enough to go to high school, why not have the third “Halloweentown” movie focus on exactly that? The fact that the kids who had watched the previous two films were also getting older themselves meant that bringing a bit of maturity to the franchise was also in order.

To that end, “Halloweentown High” takes on the guise of a high school comedy, but with the addition of magic and monsters. In an interesting decision, the film’s setting isn’t a dedicated Halloweentown school but is instead a high school in the regular world that happens to have some Halloweentown students who have transferred there.

The benefit to that decision is that it allows for more of the push-and-pull between the magical world and the regular world that made the original movie so fun and was a bit lost in the sequel. The downside is that we see much less of the first two installments’ fun creatures and monsters and a lot more boring ol’ human teenagers — which isn’t really what we watch a movie like this for. It’s a fun watch, for sure, and it does a lot of things right, but it’s impossible not to wonder how much better a movie that took place at the actual Halloweentown high school might’ve been.

Given that it would eventually become one of the longest-running Disney Channel original movie series in history, it may be surprising to learn that “Halloweentown” was originally pitched to NBC. But the Peacock Network’s loss was the House of Mouse’s gain, and the latter got an instant classic that not only stood out amongst the rest of the cable channel’s original movie fare of its day but is a legitimate entry in the canon of family-friendly Halloween movies, period, small screen or otherwise.

By now, it’s been well established that “Halloweentown” is a beloved movie, given that Disney saw fit to turn it into a full-fledged franchise that stretched beyond being a mere trilogy. Instead, it might be more productive to explain why the initial chapter in the saga missed out on the top spot on this list. It’s not the movie’s fault, as setting things up is the burden of all first entries in a movie franchise, but “Halloweentown” does drag a bit as its characters are introduced, the world is established, and the lore is laid out before things finally get going. If there was never a second movie, maybe we wouldn’t be so hard on the original for those things — but again, that’s just how it goes. Once a movie gets a sequel, they must forever be directly compared against each other.

With all the worldbuilding out of the way and Marnie having fully embraced her powers and her destiny, “Halloweentown II: Kalabar’s Revenge” was free to hit the ground running and, as a result, is a lot more fun and interesting right from the start. The main conflict was also allowed to be about something more than just Marnie’s journey to becoming a witch and finding her way in Halloweentown for the first half of its runtime, which makes the sequel inherently more exciting to watch.

Of course, it’s not a slam dunk that a sequel will surpass its predecessor. You have to successfully build on the foundation of the original, creating something that takes the established characters and setting in new, interesting directions that aren’t just a victory lap of what worked in the first movie. Enter Kalabar Jr. (Daniel Kountz), who means to avenge his defeated father from the original film.

Kal is a delightfully campy villain who torments our heroes and all of Halloweentown in interesting ways, butting up against the limits of how dark and scary Disney would allow these movies to get, taking things a bit further than the first movie was allowed to, or that either of the subsequent installments did. It’s in those ways that “Halloweentown II” manages to surpass its predecessor, cementing its status as the “Halloweentown” movie to beat.