The Adventures of Ichabod and Mister Toad : "The Legend of Sleepy Hollow"

Premiered October 5, 1949.

"I'm telling you, brother, it's a frightful sight what goes on, Halloween night. When spooks have a midnight jamboree. They break it up with fiendish glee ..."
-Brom Bones

Note from your trusted holiday bloggers:

We are only reviewing the "Ichabod" portion of this movie, since the "Mister Toad" section does not involve Halloween.

A new schoolmaster named Ichabod Crane (Bing Crosby) arrives in the town of Sleepy Hollow, New York. He quickly becomes the most popular bachelor in town, dining with women all around the little hamlet.

However, Ichabod only has eyes for Katrina Van Tassel, daughter of the wealthiest farmer in the county. Ichabod is smitten at first site, and her father Baltus's wealth doesn't diminish her attractions for him.  

This brings Icky into direct conflict with another suitor, Brom Bones. They engage in games of one upsmanship to gain Katrina's affections.

Despite Brom's physical advantage, the skinny schoolmaster always seems to come out on top, until Halloween night.

Ichabod attends Baltus van Tassel's annual Halloween party and there is plenty of food, music and dancing.   

Ichabod has a great evening, showing off his dancing skills in front of Katrina and is the life of the party.   As the evening progresses, Baltus asks his guests to tell him scary Halloween stories.  

Ichabod is very superstitious and easily frightened.  Knowing this, Brom tells the tale of the Headless Horseman.  He sings of how the horseman rides across the countryside on Halloween, looking to chop of someone's head to replace his own. 

Brom mentions that the Horseman has no power on the other side of the bridge that leads to Sleepy Hollow.  If his would-be victims can cross the bridge, they're home free.  By the end of Brom's story, Ichabod is absolutely petrified.

Crane leaves the Van Tassel's house at 2:00 AM to head back home. He is haunted by Brom's tale of the Headless Horseman. Every night sound seems to be calling out his name. The trees and plants along his path also seem to be sending messages of foreboding and impending doom. Ichabod's fears are confirmed when the Headless Horseman himself appears! The Horseman pursues Crane on a black steed with red eyes and nearly chops off Ichabod's head several times.

After a frantic chase, Ichabod sees the bridge to safety and rushes to cross it. The Headless Horseman is right behind him! Will Ichabod escape or will the Headless Horseman "get a head?"

J.A. Morris says:

I first saw this when it aired in the early 1980s as part of "A Disney Halloween" and I've been a fan ever since. It would have been easy for Disney to water down the Headless Horseman's pursuit of Ichabod. But it's a legitimately scary scene for younger audiences who aren't familiar with the story. It would have also been easy for the creative team to slap on a happy ending, which does not occur.

In Washington Irving's story, Halloween and for that matter, the month of October is never mentioned.  Irving only mentions that it takes place during autumn.  But "The Legend Of Sleepy Hollow" makes a perfect Halloween story. 

Bing Crosby has been synonymous with Christmas for 75 years. "White Christmas" is the most beloved Christmas song of all time and he hosted holiday radio and TV specials for several decades. But in The Adventures Of Ichabod, Crosby shows he can be versatile when it comes to holiday programming. He narrates and voices all the male characters in this film. "Der Bingle" also sings the "Headless Horseman" song and it's fantastic.

This film is available for streaming and has also been released on DVD and Blu-Ray.

The Adventures Of Ichabod and Mr. Toad is a great adaptation of one America's first great stories. It's highly recommended and it's something I watch every year around Halloween.


J.A. Morris' rating:

4 jack o'lanterns

RigbyMel says:

I remember seeing this on network television several times as a small child and it scaring the dickens out of me. The 1982 airing on CBS as part of "Disney's Halloween Treat" (which included the climactic portion of "The Legend of Sleepy Hollow" but not as much of the build up) particularly sticks in my mind for some reason - maybe because it had a talking jack o'lantern puppet that hosted the segments? (Possibly also because versions of this special aired on various network and cable channels throughout the 1980s.)

The animation in the "Legend of Sleepy Hollow" is impressive overall - particularly Ichabod and the Headless Horseman's scary/comic chase though the dark woods.

As J.A. Morris notes above, Bing Crosby's voice over and musical contribution to the mix makes this an extra special treat. I also appreciate how much of the narration is lifted directly from the original Washington Irving tale -- although the ending is presented as a bit more ambiguous than in the original story. (Something I did not pick up on as a small child!)

Bing Crosby and the Rhythmaire's rendition of the song "The Headless Horseman" (which also floats around as a single with slightly different lyrics) is delightfully spooky and full of excellent word play.

Fun side notes, some Disney regulars make (uncredited) vocal appearances in the this short -- Pinto Colvig (the original voice of Goofy) provides some of Ichabod's hysterical screams and Clarence "Ducky" Nash (the original voice of Donald Duck) gives voice to Ichabod's horse as well as various night time animals.

"The Legend of Sleepy Hollow" is gorgeously animated, deliciously spooky Halloween fare that can be enjoyed on multiple levels -- there are things for young and old to savor in it. It is on my required annual viewing list around Halloween each year.


RigbyMel's rating:

4 jack o'lanterns