I Watched All Four “Halloweentown” Movies For the First Time This Year

Halloweentown

The recent release (and $130 million worldwide weekend pull) of Five Nights at Freddy’s has reignited the longstanding debate about media properties ostensibly aimed at children. Earlier this year, we saw the same discourse slither onto social media when The Super Mario Bros. Movie arrived in theaters. Broadly, the theory goes, movies aimed at children are meant for children. They don’t need to be good, and it’s unreasonable for critics and audiences to hold them to account for their shortcomings. Independent of my personal thoughts on the matter, it was a nascent concern when, in the weeks leading up to Halloween, I decided to stream all four Halloweentown movies with my partner.

I understood there was a rabid, cult fanbase for what many consider to be the Disney Channel’s premier holiday spooktacular, but as an adult, I wasn’t sure how it was going to work. Without the tinted lenses of nostalgia, would my old-man, corrective lens be enough for any insights into what made the series so popular, or, as I thought, would I simply sigh and concede that the window for Halloweentown had passed?

Halloweentown

And that window is short, too, not just from my critical perspective, but for the thrust of all four Halloweentown movies. The first, directed by Duwayne Dunham, introduces the Piper clan, a brood of youngins whose mother, Gwen (Judith Hoag) reminds me a lot of an old neighbor who once told me I was going to Hell for trick-or-treating. The children, 13-year-old Marnie (Kimberly J. Brown), 12-year-old Dylan (Joey Zimmerman), and 7-year-old Sophie (Emily Roeske), are forbidden from celebrating Halloween. It’s a perennial point of contention in their copy-paste suburban home, one regularly compounded by the arrival of Debbie Reynolds’ Aggie Cromwell, Gwen’s mother, and the children’s grandmother.

It needs to be said right away that the heart and soul of Halloweentown is the late Debbie Reynolds. The Singin’ in the Rain and How the West Was Won alum is conspicuously having an absolute blast. Long-known for lighting up any screen she was on, there isn’t a beat in Halloweentown where Reynolds is present where it’s possible to have anything but a smile on your face. She’s more than just a delight—she’s positively magical.

And, well, she is. Aggie Cromwell is a witch, and once a year, the portal between the mortal world and the titular Halloweentown—a realm where monsters, witches, and the like have settled to avoid conflict with humans—opens. Marnie is of particular interest. If she doesn’t hear the truth from her mother and visit Halloweentown soon, the opportunity for her to train and cultivate her own magic powers—an ancestral Cromwell magic—will be lost forever. Marnie overhears this, and with her siblings in tow, they sneak out to follow Aggie, taking a magic bus (no Mrs. Frizzle, unfortunately) to the title town.

Is anything in the first Halloweentown groundbreaking? No. Does it qualify as gateway horror? Marginally, though it never intends to be even remotely scary. It is funny, however, and despite the dated 1998 effects (additionally constrained by a slim budget), it looks incredible. It’s gateway horror as acclimation. The vampires, ghosts, and werewolf denizens of the town aren’t monstrous beasties. Often, they’re portrayed as big dorks, goofs who couldn’t, to be cliché, hurt a fly (or an intrusive trio of kids). There’s an undercurrent of menace with Halloweentown mayor, Kalabar (Robin Thomas), a man who might well have arrived wearing a big sign that read, “BAD GUY ALERT,” but it’s a movie for kids, so they’d understandably be less inclined to pick up on Kalabar’s evil stench from the get.

Kalabar intends to take over the mortal world, though of course, Marnie and her siblings, with Aggie’s help, find the magic within themselves to stop it. There’s a broad message in here about obeying your parents but also not. It’s important to know one’s roots, yadda yadda, because the finale bludgeons its young audience over the heads with its meaning. Still, it’s cute. Really cute. So cute, I could see it on my annual Halloween viewing rotation. It’s a shame I was decades late to the party, but I’ve arrived, and I’m grateful the door remained open.

Halloweentown II: Kalabar’s Revenge

Halloweentown II: Kalabar’s Revenge released three years after the first. In the opening scene, the Piper family is hosting a neighborhood Halloween party. The mechanics don’t exactly make sense (where are all the parents, why is Gwen sending Sophie to bed in the middle of it), though it’s an easy and appreciated way to demonstrate the development between entries. They can celebrate Halloween now, and genuinely, earnestly, that made me happy.

At the party is cute boy, Kal (Daniel Kountz, Kimberly J. Brown’s real-life husband for an extra overload of adorable). Kal is clearly connected to Kalabar. Beyond the name, he arrives despite not being invited, takes an inordinate interest in Marnie, and all but forces her to return to Halloweentown and fall into his trap. She does, and in silly, Freddy Krueger rubber wall fashion, he taunts her. Ha ha, he’s been evil all along. Yeah, Kal, we know. We just don’t know how Marnie didn’t (Marnie will grow more rebellious as these movies progress, a cautionary tale for overprotective parents everywhere).

Halloweentown is again threatened, and the Piper clan must save the day. This entry is widely considered to be the darkest one in the series. It’s not surprise, seeing as Pet Sematary’s Mary Lambert is at the helm, but I personally didn’t find it that tonally different than the preceding movie. The monster effects are better and the notion of turning everyone into one based on the mask they’re wearing strikes a certain existential chord, but it’s abounding with whimsy. Plus, it’s got Debbie Reynolds sorting socks. She’s really, really into sorting socks in this movie. It’s maybe the cutest thing ever.

Resultantly, Halloweentown II: Kalabar’s Revenge is just as strong as the first. It’s an organic extension of the original, albeit a little more genre-focused. The cast remains uniformly strong, the humor is sweet (if a little saccharine), and the Halloweentown lore is developed in compelling ways. I’m a certified Halloweentown lore expert now, and that’s incredible to me.

Halloweentown High

Halloweentown High is where the franchise starts to lose me. For everything it does better than the first two, there are areas it neglects, consequently losing that distinct, autumnal Halloweentown charm. Halloweentown High is funnier, more assured, and tighter in tonal command. Conversely, it also feels like any number of early aughts DCOMs (Disney Channel Original Movies). The high school setting holds it back, forcing Halloweentown High to saunter through the same “it’s okay to be different” ethos seen a dozen times before.

At the conclusion of the last film, Marnie successfully used her magic to keep the portal between the human and monster world open permanently. Ergo, she figures, it makes sense to allow several Halloweentown monsters to enroll in her local high school. Hijinks ensue, and somehow, Aggie Cromwell is allowed to teach there, despite there being no indication ever before that she’s qualified to do so.

All the while, a new, arbitrary threat is introduced in the form of the alleged Knights of the Iron Dagger, an ancient legion hellbent on destroying magic everywhere. Oh, and Marnie meets Finn Wittrock’s Cody Trainer, a cute new boy (whom I kept expecting to be a serial killer), totally ignoring love interest Luke (Phillip Van Dyke) from the previous two movies.

Here, Kimberly J. Brown is more confident than ever, and unlike the prior two entries, she steals the show, gamely leaning into Marnie’s caustic wit and sheer incredulity toward the chaos around her. It’s passably entertaining, even if it never feels like a Halloweentown movie.  It would, however, be the last true one (at least according to fans).

Return to Halloweentown

It’s only been a week since I’ve seen these movies, so I’m not comfortable calling Return to Halloweentown the travesty fans contend it to be. I am confident in saying that, despite Sara Paxton’s best efforts (really, she’s not bad here, so please leave her alone), it’s weird to see a Halloweentown movie where the only new face is Marnie’s. Kimberly J. Brown, despite being available at the time, is arbitrarily shafted for Paxton. Had there been some kind of reasonable conflict, sure, replace her. Brown, however, has been vocal that she has no greater insight into the replacement than the rest of us, so it reeks of mean-spiritedness more than most recasts.

It doesn’t help that Return to Halloweentown regularly feels lazy. Listen, these are Halloweentown movies. I went into this expecting to miss the point entirely. I don’t think I did. They’re fun time capsules, cute bits of family fun with enough Halloween zest to endure. Return to Halloweentown really, really wants to be Harry Potter on a DCOM budget, and it rarely works.

The conflict is shoehorned, the twists dull, and as a capstone to the rare Disney Channel Original Movie to get three (!!!) sequels, it does nothing to wrap the series up cohesively. It feels like a side story, one so beholden to the magic craze at the time, it never manages to be anything more than a Potter pastiche. Hard pass, Return to Halloweentown. Points for the cute dog, but I don’t have anything else to credit you for.

And that’s it! I watched four movies aimed at kids and I liked them. Would I feel more passionately had I grown up with them? Probably, but my mom was irresponsible and skipped the whole gateway part to throw me straight into the deep end. They’re cute movies, and after decades, I finally understand the jubilation those around me have when that signature theme kicks in. Halloweentown is a cup of cocoa on a cold October evening. In a decade

All 4 Halloweentown movies are presently available to stream on Disney+

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