Oak Cliff Review: “The Spirit of Halloweentown”

[Billy Ray Brewton, no stranger to film criticism and filmmaking, joins Film Festival Today for coverage of the 2025 Oak Cliff Film Festival.]

Now in its fourteenth year, Dallas’s  Oak Cliff Film Festival has continued to expand its reputation as one of the most eclectic, filmmaker-forward festivals on the circuit. Consistently ranked as one of the best festivals in the United States, Oak Cliff utilizes gorgeous, historic theaters and showcases films from all over the world, setting the stage for a mixture of Texas hospitality and punk-rock ideologies surrounded by cinephiles from all walks of life. What follows is my review of a new documentary that just played there.

The Spirit of Halloweentown (Bradford Thomason/Brett Whitcomb, 2024) 4 out of 5 stars

During my tenure as Head of Programming for Rooftop Cinema Club, no film consistently surprised me with its performance more than Halloweentown, the 1998 Disney Channel original starring Debbie Reynolds as a wacky grandmother who travels to the titular town, grandkids in tow, on a magical bus. It became an instant hit with viewers, and went on to become something of a cult sensation for an entire generation. At Rooftop, we would screen it multiple times each Halloween, at cities all over the U.S. and in the U.K., and it would quite literally sell out 100% of the time. It still does. It’s a bona fide “butts in seats” sure thing.

The Spirit of Halloweentown is about the classic film … sort of … or, well, not at all, really. It’s more of a celebration and exploration where Halloweentown was filmed, a charming little town in Oregon called St. Helens. We are told that multiple generations of families have lived there, and to not mess up on social media or you’ll be forever shunned. Stylistically, it feels more akin to a Frederick Wiseman documentary about small-town life, though far shorter. In fact, it’s the subversion of expectations for a documentary like this that makes it so rewarding. This is not your typical nonfiction piece in any sense, employing a combination of vérité, unproduced talking-heads segments, and the juggling of multiple threads around town.

The prominent “characters” here are never dull. There’s the gay outsider who has recently purchased a local tavern and tries to recover from a social-media faux pas that has left him reeling. There’s the team of ghost hunters capturing shockingly convincing evidence of hauntings throughout the town, hauntings that some locals refuse to even speak about. There’s the religious zealot who thinks the celebration of Halloween is the devil’s work as she serenades attendees with hymns and Jesus-loving originals. And, most effectively, there’s the recent high-school graduate choreographing a cheer routine for the festivities, while at the same time struggling to come to terms with an absentee father who would rather stay absent.

Is Halloweentown mentioned? Absolutely. Does it hang over the entire film? Of course. But filmmakers Bradford Thomason and Brett Whitcomb know how to take an interesting subject and turn it on its head, just as they did with the heralded-but-under-seen, Jasper Mall. They wisely avoid footage from the film and interviews about the film, but rather focus on how it has affected both the town and the people who live there, as its success opened a door to big tourism dollars for a town that desperately needed them. Removing Halloweentown from the equation altogether wouldn’t even hurt the documentary, really; it’s flavor, but not the sauce. The sauce comes in many forms, such as when a local seamstress (also known as the “The Queen of Halloweentown”) talks about the struggle to find joy in the festivities after dealing with the recent loss of her mother (her “best friend”). Those moments are emotionally delicious.

I wish more documentaries would take these kinds of risks, rather than feel so beholden to their source material. Clearly, fans seeking out the film to get their nostalgic Halloweentown kicks will start out disappointed, but I can’t imagine they wouldn’t get sucked into the stories being told by characters just as fascinating as any featured in the original narrative. Sure, there might not be witches or ghouls, but I’d argue the zombie-cheer routine is as magical as anything Debbie Reynolds helps conjure on screen. And I dare you not to be weirdly haunted by the final image in the film, an image which leaves so many unanswered questions. The Spirit of Halloweentown is just that: a joyous and inspiring reminder that towns can come together, people can work towards a common good, and the magic and power of cinema has a reach far beyond a television screen in 1998. In this film, the real magic is St. Helens itself.

Billy Ray Brewton

Billy Ray Brewton is the producer and founder of Make Believe Theatricals, which specializes in promoting unique creative voices that exist outside the mainstream. Billy Ray was the subject of the award-winning documentary, Skanks (Slamdance 2014); wrote and directed the award-winning dramatic horror film Show Yourself (Bruce Campbell’s Horror Film Fest 2017); produced the award-winning documentary Socks on Fire (Tribeca 2020, “Best Documentary Feature”); and served as associate producer on the horror anthology, The Mortuary Collection (Fantastic Fest 2019, “Audience Choice Best Feature”). The short film he produced in 2016, Pool Shark, currently has over 100 million views on YouTube. His next project as a producer, Mental Health and Horror, is scheduled for release in 2025. He is a member of the Dramatists Guild, IDA, and Documentary Producers Alliance; is the ultimate heel on the Screen Drafts podcast; and writes about film for Cinepunx.