Halloween is one of our favorite holidays here at Pop Break, and we’ve been celebrating all week long by highlighting some of our current, and all-time favorite pieces of pop culture related to Halloween. This year, we’re gathering a team of writers to extol the virtues of their favorite Spooky Season animated watches.
The Adventures of Ichabod and Mr. Toad (The Legend of Sleepy Hollow)
Release Date: 1949
Vocal Cast: Bing Crosby, Basil Rathbone, Eric Blore, Pat O’Malley, John Ployardt, Colin Campbell, Campbell Grant, Claude Allister and The Rhythmaires.
Watch on: Disney+
Chosen by: Brandon Hilton – Pop Break Contributor, Co-Host of The Court of Bros & Spice.
Fall/Spooky Season is my favorite and best time of the year. I can’t think of a better animated film to watch to get into the Halloween spirit than the 1949 Disney animated short, The Legend of Sleepy Hollow. It is the second segment of The Adventures of Ichabod and Mr. Toad. You learn about the lore of the Headless Horseman and the darkness found in the small town of Sleepy Hollow. This animated feature is a testament to the versatile range of animation, art style, use of color, and themes that Disney was able to create.
Bing Crosby’s narration, vocal range, and songs help bring out the short’s fun, spooky vibes, especially at the end when he narrates how creeped out he is and leaves. This short is dark, sinister, and supernatural, but it still has comedic moments and a dazzling display of colors and palettes. The movie is intended for kids, but adults will connect with the references, themes, and nostalgia.
As a child, I was amazed and a little scared by this short because of the art, music, and storytelling, but I think that is what lets it transcend age and keep tormenting and drawing in future generations. This is a must-watch short once Fall comes and the weather changes. It is a great spooky visual definition of Halloween, sets the tone for this season, and will have you looking into taking a tour of Sleepy Hollow to learn more about Washington Irving’s work.
Gravity Falls
Year Released: 2012 (ran to 2016)
Vocal Cast: Jason Ritter, Kristen Schaal, Alex Hirsch, Linda Cardellini
Stream On: Disney+
Chosen by: Gabrielle Sangataldo (Music Writer, Co-Editor-in-Chief, The Underground Edit)
For a show set entirely over the course of one summer, Gravity Falls is undoubtedly perfect for getting into the Halloween spirit. Between a triangle-shaped demon with a knack for unleashing unfathomable chaos and an endless parade of freaky monsters, Gravity Falls is less a Disney Channel kids’ show and more a testament to how talented the creators must be to keep it rated G.
Gravity Falls exudes fall—no pun intended—vibes and is funny enough to keep things light while still satisfying that Halloween craving for something unsettling, mysterious, and supernatural. It’s casual enough that you can leave it on as background noise while still providing a plot that is as binge-worthy as it is gripping. Beyond the nostalgia of revisiting a familiar and weird fictional world, I rewatch it every time the temperature dips below 60 degrees for one reason: pure fall campiness.
If you won’t commit to the whole series just yet, watch Season 1, Episode 12, “Summerween,” to get a glimpse of what you’re missing and a perfect excuse to embrace Halloween.
Vampire Hunter D: Bloodlust
Year Released: 2001
Vocal Cast (U.S.): Andy Philpot, Pamela Adlon, John Rafter Lee, Dwight Schulz, John DiMaggio, Wendee Lee, Julia Fletcher, Matt McKenzie
Stream on: Prime Video
Chosen by: Amandas Rivas (Co-Host Socially Distanced Podcast, Anime x Pop)
As soon as the opportunity to contribute to this piece came up, immediately I heard the voice of our Editor-in-Chief and my dear friend Bill Bodkin in my head asking “so which anime are you going to recommend?” Anime does offer several outstanding stories that are perfect for this time of year. My recommendation is more appropriate for older teens and adults as some of the scenes can be intense for small children.
2000’s Vampire Hunter D: Bloodlust is a beautiful gothic dark fantasy vampire film following D, a dhampir (half human/half vampire), as he accepts a bounty to rescue Charlotte Elbourne, a young human woman who has been abducted by powerful vampire Meier Link. Viewers watch D as he continuously struggles trying to exist in a world where he is shunned by both humans and vampires, engages with strong supporting characters such as the Marcus Brothers, and learns that things are not always what they seem while trying to rescue Charlotte.
This film is considered one of the most beautifully animated anime projects of all time with strong voice performances in both the English dub and Japanese sub. The overall gothic look, soundtrack, and costumes all are perfect for this Halloween season. D is one of the most charismatic characters in this space as his adventures continue to capture our imaginations over 40 years later with a new manga in development and a comic book series currently scheduled for release later this year. This is a fantastic watch for both seasoned anime fans and those who have very little exposure to anime wanting a fun, spooky watch.
The Skeleton Dance, a Disney Silly Symphony
Release Date: 1929
Vocal Cast: Walt Disney, Carl W. Stalling
Stream on: Disney+
Chosen by: Randy Allain (Co-Host of Podelay!, The Hope of It All, Media/Lit)
I can’t tell you the first time I watched The Skeleton Dance, but I was most likely nestled in my childhood living room enjoying the great privilege of a Disney cable subscription. Perhaps after kicking my day off with some Mousercise, I hit the soccer field and scarfed down a donut before settling in for a cool fall day. As the evening set in, perhaps I took to the couch to see what Mickey and pals were up to that day; instead, I encountered a deceptively macabre cartoon that haunts and delights me to this day.
From a distance, The Skeleton Dance offers harmless fun in the form of silly skeletons grooving the night away; yet, there is something unsettling beneath the playful sounds. First, there is the simple fact that it hails from another era. This piece is nearly one-hundred years old, and just below the upbeat tune lurks that staticky void of audio imperfection that only comes from age. The sound itself feels haunted, evoking spooky memories of long lost creators and the dawn of a great depression that would finish taking form on Black Thursday, about two months after the premiere of this cartoon. If that’s not enough to awaken your spooky side, consider the unnaturally shifting and elongated bones of the skeletons, their willingness to hurl their skulls as weapons, or their tendency to deconstruct one another to form crude instruments. In the closing moments of the short, these twisted denizens of the underworld reconfigure themselves into a crude, four-headed horseman of the apocalypse that would be just as comfortable on the cover of a metal album as it is rubbing (bony) elbows with Mickey Mouse from the afterlife.
Ducktales Season 3, Episode 10, “The Trickening!”
Release Date: 2020
Vocal Cast: David Tennant, Danny Pudi, Ben Schwartz, Bobby Moynihan, Kate Micucci, Beck Bennett, Paget Brewster, Tony Anselmo with special guests Doug Jones, Clancy Brown, James Marsters, and Selma Blair.
Stream on: Disney+
Chosen by: Bill Bodkin (Editor-in-Chief)
There’s so many great Spooky Season picks on Disney+ Whether it’s the Kiff specials “Trevor’s Rockin’ Halloween Bash” (2023) or the legit frightening “The Haunting of Miss McGravy’s House” (2024), the classic “Trick or Treat,” or “The Scariest Story Ever: A Mickey Mouse Haunted Spooktacular” (2017). However, it’s the revival of Ducktales and its Halloween episode, “The Trickening!” which takes the candy for me. As this revival was wont to do, plays to both the kiddos and their nostalgia-hungry parents. The subplot of the episode being that Launchpad McQuack believes he cursed the world on Halloween night by reading an ancient text (ingredients to candy) is hilarious, and is bolstered by both Beck Bennett’s wondrously dunderous performance of the accident-prone pilot, and Della Duck’s (Padget Brewster) utter fascination with the predicament.
Toy Story of Terror!
Release Date: 2013
Vocal Cast: Tom Hanks, Tim Allen, Joan Cusack, Carl Weathers, Timothy Dalton, Don Rickles, Wallace Shawn, Kristen Schaal, Stephen Tobolowsky, Tara Strong, Dee Bradley Baker, Ken Marino, Laraine Newman.
Stream on: Disney+
Chosen by: Bill Bodkin (Editor-in-Chief)
While this may not be the most obscure or deep-cut choice for this list, it’s still one of my favorite television specials to watch on Halloween.
Toy Story of Terror is a delightful 30-minute special (21 minutes, actually) that finds all your Toy Story pals stuck in a motel run by an unscrupulous hotel manager (voiced by Stephen Tobolowsky, a.k.a. Ned Ryerson from Groundhog Day). The manager, like most villains in this series, wants the toys for his own personal collection so he can sell them off to the highest bidder. The story is framed like an old-timey horror story, thanks to the continuous narration of one of my all-time favorite animated characters, Mr. Pricklepants (Timothy Dalton). We also get the fantastic addition of Combat Carl, voiced by the late Carl Weathers, in all his hyper-masculine glory.
Nothing in this special is scary, but it’s truly charming and a joy to watch. All the voices from the Toy Story movies are here, and it’s just great to see all these characters doing their thing onscreen — and a nice pairing with Toy Story 5. If you have kids, this is a must-watch. (This write-up originally appeared in our 2017 “Best Halloween Specials/Episodes” article).
The Nightmare Before Christmas
Release Date: 1993
Vocal Cast: Danny Elfman, Chris Sarandon, Catherine O’Hara, William Hickey, Glen Shadix, Paul Reubens, Ken Page, Ed Ivory
Stream On: Disney+
Chosen by: Bill Bodkin (Editor-in-Chief)
As my daughter once told me, “This is the perfect movie … you can watch it during Halloween and Christmas!” She is not wrong. One of the most beautifully animated, timeless pieces of cinema is not just a visual delight, it’s got incredible songs, amazing characters, and a story full of heart and fright. Perfection.
