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[Slay the Date] The Spirit of Halloween

Slay The Date is a bi-monthly column bringing you something different, compelling, and fun with each edition. Justin Lockwood shares with us his favorite horror films for every season.


The Halloween season is rife with horror films offering treats for audiences of all ages.

The Adventures of Ichabod and Mr. Toad (1949), directed by Clyde Geronimi, Jack Kinney, James Algar.
The hunt is on in The Adventures of Ichabod and Mr. Toad (1949)

While the combination of Halloween and horror is natural, comparatively few horror films are set on the holiday. Perhaps the iconic benchmark set by John Carpenter’s Halloween (1978) scared off other filmmakers. The numerous slasher clones of Halloween, led by Friday the 13th (1980), tended to co-opt other holidays, albeit with similar killers and a tenacious formula. Halloween is my favorite holiday, as I’m sure it is for many of you, so I’m particularly selective about the movies that best exemplify it.

The first great Halloween-oriented movie wasn’t a horror film, at least not in the traditional sense. It was The Adventures of Ichabod and Mr. Toad (1949), directed by Clyde Geronimi, Jack Kinney, and James Algar and produced by Walt Disney. While it also includes an adaptation of Kenneth Grahame’s The Wind in the Willows, the film is best remembered for its unequaled adaptation of Washington Irving’s classic short story "The Legend of Sleepy Hollow." Published in 1819, the story predates Halloween, but the Disney adaptation ignores that and makes the climactic celebration a Halloween party while giving the Horseman a flaming jack-o-lantern head.

The thoroughly enjoyable tale has a self-centered, womanizing schoolteacher named Ichabod Crane eyeing the love and fortune of gorgeous Katrina Van Tassell. Ichabod gets his just desserts at the hands of a local "ghost," more than likely his rival Brom Bones taking advantage of his superstitious nature. Bing Crosby narrates and performs original songs, most notably "The Headless Horseman," which sets up the film’s signature chase scene through the eerie woods of Sleepy Hollow. The confrontation between Ichabod, the Horseman, and their steeds rivals anything produced in live action for chills and thrills. The vivid visuals and unforgettable scares of this terrific animated production cemented the connection between Sleepy Hollow and Halloween forevermore.

Jamie Lee Curtis as Laurie Strode in John Carpenter's HALLOWEEN (1978).
Laurie Strode (Jamie Lee Curtis) faces The Shape in Halloween (1978)

Surprisingly, very few productions, horror or otherwise, centered their plotline on Halloween until Carpenter co-wrote with Debra Hill and directed the independent box office hit, Halloween. A notable exception is the television special It’s the Great Pumpkin, Charlie Brown (1965). On Halloween night in 1963, six-year-old Michael Myers kills his sister Judith while outfitted as a clown. He later breaks out of the psychiatric asylum that's housed him 15 years later to don a new costume and carry out a series of merciless murders.

Shy bookworm and babysitter Laurie Strode (Jamie Lee Curtis) and her friends Annie (Nancy Loomis) and Lynda (P.J. Soles) settle in for a fun, relaxing night, not realizing The Shape is lurking in the shadows. Carpenter and Hill play with the Halloween setting, drawing inspiration from the folklore of Samhain with touches like glowing jack-o-lanterns (the opening title sequence memorably features one), an autumnal theme for Laurie, and some of Carpenter's favorite horror and science fiction movies playing on television, like The Thing From Another World (1951), which he'd remake in 1982.

"Modern Halloween is just as much about denying death its power as it is a surrender to it."

Michael is given a mythic quality through his inscrutable nature and the feverish imaginations of the local children. "Every kid in Haddonfield thinks this place is haunted," Sheriff Brackett (Charles Cyphers) tells Doctor Samuel Loomis (Donald Pleasence), Michael’s warden. "They may be right," Loomis replies. "The Halloween phenomenon reconnected the holiday to its primary, if forgotten, cultural purpose: a ceremonial acknowledgment of mortality and the never-ending cycles of life, death, and the mysteries that follow," author and historian David J. Skall writes in Fright Favorites: 31 Movies to Haunt Your Halloween and Beyond (2020). "Before John Carpenter reinvigorated the holiday with ritual human sacrifice, did anyone still make a conscious connection between a jack-o-lantern and a grinning skull? Modern Halloween is just as much about denying death its power as it is a surrender to it—a grim game of hide-and-seek with a relentlessly determined reaper."

Halloween is a cult classic exploiting the holiday’s atmosphere, but it’s not really about Halloween. For that, audiences would have to wait for its innovative sequel, Halloween III: Season of the Witch (1982), which continues the themes of Celtic mythology and Paganism introduced in Halloween II (1981) in a more appropriate format. It didn’t make much sense for Michael to scrawl "Samhain" in blood—apparently staring at a wall for fifteen years gave him time to ponder his doctoral thesis on ancient religion—but in the unrelated Halloween III, villainous warlock Conal Cochran (Dan O’Herlihy) is fully aware of the dark power of the holiday. A successful toy and mask maker, he plans to carry out a ritual sacrifice on a grand scale: murdering millions of children wearing his signature Halloween masks.

Tom Atkins and Stacey Nelkin in John Carpenter's Halloween III: Season of the Witch (1982).
Dr. Daniel "Dan" Challis (Tom Atkins) and Ellie Grimbridge (Stacey Nelkin) in Halloween III (1982)

The themes of witchcraft, not to mention a moody score composed by Carpenter and gorgeous cinematography by Dean Cundey, add up to a darkly comedic and rewardingly offbeat movie about Halloween. Initially rejected by audiences hungry for more Michael Myers, the film has become a beloved cult classic.

Arguably, the ultimate Halloween-centric horror film is Michael Dougherty’s cult classic Trick ‘r Treat (2009). Originally dumped onto DVD, the film has since received the following it richly deserves. The funny and frightening film interweaves five different storylines in a small Ohio town on Halloween night. The characters range from a murderous principal (Dylan Baker) to a seemingly shy virgin (Anna Paquin), and a group of school kids making a pilgrimage to the site of the "Halloween Schoolbus Massacre."

Sam (Quinn Lord), a mysterious little creature that may be the spirit of Halloween itself is never far away. The rich and detailed screenplay captures the experience of Halloween at various stages of life and provides twists and turns worthy of this most surprising and magical of nights. It also acknowledges the holiday’s Pagan roots as Samhain—pronounced correctly, for once, as "sow-en." Eagle-eyed viewers will spot characters in the background of each other’s storylines. Dougherty directs with an assured hand and delivers a delicious Halloween atmosphere throughout—the sequence set to "Sweet Dreams (Are Made of This)," is one of my favorite scenes in all of horror. Dougherty has hinted at a sequel for several years, but it’s probably for the best that it didn’t happen. Trick 'r' Treat would be hard to top.

Quinn Lord in Michael Dougherty's Trick 'r' Treat (2009).
Sam (Quinn Lord) in Trick 'r' Treat (2009)

Trick ‘r Treat, particularly the character of Sam, was inspired by Henry Selick’s animated classic The Nightmare Before Christmas (1993), based on the poem by Tim Burton and featuring unforgettable songs by Danny Elfman. It’s one of my favorite films and among the greatest depictions of Halloween ever made. Jack Skellington, the king of Halloweentown, is bored of presiding over the holiday and yearns for something more. After accidentally stumbling across Christmastown, he decides to give Santa Claus "a vacation" and take it over himself, with predictably disastrous results. The opening number, "This Is Halloween," is a feast of eye candy and wonderfully macabre music that thrilled me as a kid. Halloweentown and its denizens are wonderfully spooky and endearing. Given that much of the plot revolves around Christmas and concludes on Christmas Eve, I tend to watch the film in December, but I’d happily argue with anyone who considers it a Halloween movie and watches it this month.

In fact, 1993 was a high-water mark for child-friendly Halloween films, with Disney also releasing Hocus Pocus, directed by Kenny Ortega and starring Bette Midler, Kathy Najimy, and Sarah Jessica Parker as a trio of Salem witches. I’d like to acknowledge that Midler's controversial tweet this past summer has been widely interpreted as transphobic and offensive. The actress insisted that was not the intent, but for many, the incident casts a shadow over Hocus Pocus and its sequel. With that said, the film undoubtedly has a significant role in horror and pop culture.

The film didn’t start off as the beloved Halloween classic it’s become—inexplicably released in July, it received poor reviews and weak box office returns. Like The Nightmare Before Christmas, which was released through Disney’s "adult" Touchstone Pictures division, it was considered potentially too ghoulish for kids. Cut to nearly thirty years later, and the film is so adored that it’s spawned merchandise and a new sequel this year starring all three original leads. Hocus Pocus is a colorful celebration of all things Halloween, with the witches facing off against young Max (Omri Katz), his little sister Dani (Thora Birch), and Max’s love interest Allison (Vinessa Shaw) for the souls of Salem’s children. It cheerfully ignores the actual grim history of the Salem Witch Trials, however, it reinforces the historical connection between Halloween, witches, and their enduring role as a seasonal icon. It’s hard not to be won over by the film’s broad charms including Midler’s show-stopping performance of "I Put a Spell on You."

Thora Birch, Omri Katz and Vinessa Shaw in Kenny Ortega's HOCUS POCUS (1993).
Dani (Thora Birch), Max (Omri Katz), and Allison (Vinessa Shaw) in Hocus Pocus (1993)

The recent revival of the Halloween franchise has given us new seasonal scares—with significantly more Halloween production value, thanks to budgets creators Carpenter and Hill could only dream of. However, my favorite Halloween horror film of the last decade was another indie production: Chris LaMartina’s clever WNUF Halloween Special (2013). Crafted with obvious care, the film purports to be a videotape of an actual, infamous Halloween broadcast from the 1980s. Snarky local television host Frank Stewart (Paul Fahrenkopf) promises to take viewers inside a "real" haunted house, accompanied by famous psychic researchers Louis (Brian St. August) and Claire Berger (Helenmarry Ball). Any resemblance between the Bergers and Ed and Lorraine Warren is purely intentional.

LaMartina directs his cast to note-perfect mockumentary performances and cleverly weaves a narrative through the local news, broadcast, and commercials (several other directors worked on the latter). Those fake commercials are a true highlight, evoking memories of 80s television for anyone who lived through the decade. WNUF Halloween Special also captures the feel of Halloween from that time, which many of us fondly look back on. This year we’ve been blessed with a 90s set sequel, Out There Halloween Mega Tape, which nails that decade as surely as its predecessor captured the 80s. It’s not quite as perfect as its predecessor, but it’s once again a whole lot of fun.

It’s hard to pick one "perfect" Halloween film—but then again, why would anyone want to? Whether you feel like a slasher or a supernatural tale—I'd recommend Kevin Tenney's campy Night of the Demons (1988), and Brad Silberling’s family-friendly Casper (1995) starring Devon Sawa and Christina Ricci—there’s a great Halloween movie for every mood. The films that capture the chills and thrills of the holiday wear as many masks as those who love them.


Justin Lockwood is a Brooklyn-based film writer, and contributor for Fangoria, Bloody Disgusting, Scream Magazine, and many more in addition to being a lover of campy, “Psychotronic” B movies. He's a lifelong horror fan and recurring guest on the Slay Away horror podcast.


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