Ranking the Halloweentown Movies: Are They As Good As We Remember?

Disney Channel was a staple of my childhood, and nothing quite signified the transition into October like reruns of the Halloweentown series. Although I look back on the franchise with fondness, I’ve begun to wonder whether the movies were actually good. After all, nostalgia can make us look back on the media from our childhood with rose-colored glasses.

I decided to investigate. What ensued was a Disney+ marathon of all four films in order. I tried my best to remain critical while also allowing myself to enjoy the experience. Below, I’ve ranked each film on its overall enjoyability, taking into consideration the sturdiness of the plot, the world building, and character development. Beware of spoilers!

  1. 1. Halloweentown High (2004)

    I’ll confess— this movie was my favorite of the bunch as a kid. For the first time, creatures from Halloweentown are brought into the human world; Marnie hosts a group of Halloweentown teens to come attend high school with her as “transfer” students. We’re exposed to a new environment while simultaneously holding onto all of the characters we love and getting to know new ones. Since the last film, the Cromwell/Piper household has become much more open to the casual use of magic. It’s surprising that they got away with so much witch activity without arousing higher suspicions from humans. The improvement in production value is strikingly noticeable, making the special effects much more polished. 

    This third film takes the budding human vs creature concept from the first two installments and develops the idea. We’re introduced to creatures who think humans are boring and cruel, and humans who think monsters are freaky and imaginary. In the meantime, Marnie, who has roots in both Halloweentown and the human world, struggles to unite both sides. Although she is open to and encourages peace, it is difficult for her to convince the creatures and humans to reconcile their differences. However, she steps up to the plate and in true DCOM fashion, the two groups come to understand and accept each other by the end of the movie.

  2. 2. Halloweentown (1998)

    I have to give credit to the film that started it all. This first installment introduced a generation of children, including the Cromwell kids themselves, to Halloweentown. It’s a comforting coming-of-age story that just happens to have all of the great elements of any classic Halloween flick. Although the exposition takes a while to wrap up, the main plot is worth the wait. This movie does some impressive world-building with details that bring an unfamiliar, potentially frightening place to life. From introducing us to the many creatures that inhabit Halloweentown to throwing in tiny monster-themed puns, we’re taught not to fear the werewolves, witches, and goblins— they’re just like us, more or less. 

    There are two characters that really make this movie great. First, Aggie Cromwell: professional witch, devoted grandmother, and total firecracker. Portrayed by the late Debbie Reynolds, Aggie is the glue that holds the films together— hence why her absence in the final film was so disappointing. Her constant encouragement is the only reason Marnie, Dylan, and Sophie could successfully save Halloweentown— she set the foundation for them. Even if they weren’t trained in magic, they knew they had a supportive figure in their corner. Secondly, there’s our villain, Kalabar. He is initially introduced as the mayor of Halloweentown and eventually revealed as the sinister being behind its possible downfall. Kalabar is a genuinely likeable character for a majority of the movie, which makes his true intentions all the more shocking.

  3. 3. Return to Halloweentown (2006)

    The fourth movie of the franchise was a strong contender for my second place slot, but ultimately there were some key factors that bumped it down to third. In this fish-out-of-water story, Marnie and Dylan go off to college at Witch University, separating themselves from the rest of the family; while their mother Gwen occasionally shows up to express how much she misses her children, Aggie only appears in two scenes, and Sophie doesn’t make a single cameo. While it’s a major change of pace, it manages to hold itself together. 

    Fortunately for this movie, the college landscape is automatically going to make it more compelling— it’s fresh, unexplored ground. I definitely blame Marnie’s dorm experience for overblowing my expectations for on-campus housing. Can you blame me? She lives in the room of a former princess and doesn’t even have a roommate! The biggest issue I couldn’t ignore was the sudden casting change— Marnie was no longer played by Kimberly J. Brown who portrayed her for the past three films. Instead, she was replaced by Sara Paxton, known for her starring role in Aquamarine. Despite her best efforts, Paxton did not embody the easy, quirky charm that I had come to associate Marnie with. All in all, though, this film was an appropriate sendoff for the series that showed just how much our protagonists had grown.

  4. 4. Halloweentown II: Kalabar’s Revenge (2001)

    At the bottom of our list, we’ve got the second installment of the series. This first sequel has some admirable qualities: the audience got to see the kids grow up a bit, and the ending altered the status quo of the entire Halloweentown universe. In case you have no clue what I’m talking about, here’s a brief synopsis. Kalabar’s son casts a grey spell over Halloweentown, making that entire world depressed and colorless. When Marnie and Aggie get trapped in Halloweentown, they work together with the rest of the family to get back to the human world, opening the portal permanently. From here on out, travel between Halloweentown is easily accessible and available year-round. 

    Sadly, this change was the best thing that the movie really had to offer (you know, other than the new character Gort, Halloweentown’s residential junkman). The core problem is the villain, Kal. From the outset, he’s too obviously creepy to not be perceived as a villain- it’s not shocking to find out that he’s a devious punk. You never really fear him or think he’ll beat the Cromwells, so their final showdown at the end is underwhelming and predictable. I repeatedly checked on the timestamp throughout the movie, waiting for it to get to the point and end. Luckily, the following sequels stepped up their game and were entertaining throughout.

My final verdict? The bias of nostalgia aside, the Halloweentown series holds up. All four films have something worthwhile to contribute to your spooky Halloween movie marathon. Reunite with the Cromwells before October comes to an end.

Happy Halloween!

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