Welcome to 31 DVDs of Halloween! As part of my Halloween Countdown, each day from now until the end of October I’ll be sharing one of my favorite Halloween movies, cartoons, or old TV specials from my personal DVD collection.

#1 – Disney’s The Legend of Sleepy Hollow

I decided to kick things off with a true classic and one of my all-time favorites, Disney’s The Legend of Sleepy Hollow.

The Adventures of Ichabod and Mr. Toad - Front

Narrated by Bing Crosby, Disney’s The Legend of Sleepy Hollow was released in 1949–that’s 32 years before I was born! Though I cannot recall the first time I ever saw it, I do know it has been required Halloween viewing for me since a very early age. Growing up, my parents must have subscribed to a good cable package because I remember always having the Disney channel and films like this would air around Halloween on The Wonderful World of Disney. The Legend of Sleepy Hollow is a relic from Disney’s dark ages–a time when Disney had the balls to make children’s films that were actually scary. I, along with many others, consider it to be a masterpiece of storytelling and animation.

The Adventures of Ichabod and Mr. Toad - Back Cover

Now, those of you who collect Disney films probably already know that The Legend of Sleepy Hollow has never gotten a standalone DVD release. The only DVD release that I know of is this compilation disc called The Adventures of Ichabod and Mr. Toad, which includes both The Wind in the Willows (starring Mr. Toad) and The Legend of Sleepy Hollow (starring Ichabod Crane). It wasn’t until recent years that this film was even available on DVD, as Disney tends to greedily horde its best content, keeping treasures like this buried deep within the mythical Disney vault. For the longest time my only copy of this film was a battered VHS tape that my parents had recorded from TV.

The Adventures of Ichabod and Mr. Toad - Disc

Of course, the quality is hundreds of times better on this DVD than it is on that original recorded VHS tape which saw a lot of wear and tear over the years. But the one thing this DVD lacks which my original VHS recording had is a bit of a surprise ending where we get to see Bing Crosby in the flesh as he jokes, “Man, I’m getting out of here too!” I kind of wish that was included here.

The Adventures of Ichabod and Mr. Toad - Special Features

You Can’t Reason with a Headless Man!

My favorite song in The Legend of Sleepy Hollow is this one that Brom Bones (Bing Crosby) sings about The Headless Horseman at the Van Tessel’s Halloween party:


My older sister and I learned all the words so that we could sing along with it every Halloween. When I was very little I used to be really creeped out by the old guy that says “…and some don’t even wear their skin!” (seen at 0:21 in the video). Hearing this song never fails to put me in the Halloween spirit.

Spooky Screencaps

Sleepy Hollow Witching Hour

Brom Bones Ghost Story

Ichabod Crane & The Headless Horseman

The Headless Horseman

Covered Bridge of Sleepy Hollow

What is 31 DVDs of Halloween?

As a special feature for the Halloween Countdown, I’m showcasing 31 Halloween DVDs from my personal collection. I have a lot of Halloween-related and horror DVDs in general, but for this year’s countdown I’m only going to focus on my absolute favorites–the ones I consider 100% essential for my enjoyment of the holiday.