TGIF: The Legend of Sleepy Hollow

Sleepy Hollow brings me back to grade school. Most of my Literature teachers included the short story in October and Halloween unit studies. I’ve read and watched different editions of the story. Since it’s Friday and Halloween Weekend, I decided to go in on The Legend of Sleepy Hollow with a focus on Ichabod Crane and the Headless Horseman. So, where did this journey begin? It started with a short story by Washington Irving and ended with a class viewing of The Adventures of Ichabod.

The Adventures of Ichabod and Mr. Toad (1949) G 68 m

It seems like Ichabod Crane tried to have his cake and eat it too. Is this a tale about how a newcomer got greedy and was chased out of town by a love rival? It seems that way to me. This Disney 2-D version of the legend tells the viewer more about Ichabod Crane than the headless horseman. Maybe that’s why my teachers got away with showing it to the class on VHS.

Ichabod Crane and
Ichabod Crane dancing with Katrina Van Tassle

Overall, it doesn’t take to many creative liberties with the story. Its definitely a good way to get students to discuss the similarities and differences. Ichabod was a smart but destitute man who sought out underhanded ways to meet his needs. Katrina Van Tassle was a selfish person that enjoyed men competing for her affection with no clear victor in mind. Brom Bones believed his wealth, appearance, and station within the town meant he alone was entitled to Katrina’s love and her family’s wealth. Since, Katrina entertained Ichabod’s advances, Ichabod had to go. Since, Irving’s ending is murky. The Legend of Sleepy Hollow can be adapted in different ways.

The Hollow (2004) R 83 m

I thought I watched The Hollow on Nickelodeon. Turns out, it was a TV movie that aired on ABC Family on October 24, 2004. Although Nick Carter, Backstreet Boy, was in the movie, I watched it for Kevin Zegers. To give you some context, Sleepy Hollow is a fairly peaceful place. Kind of like Gilmore Girls Star Hallows. Until, Ichabod Cranes’ descendant returns. Unaware that Ian Cranston has awakened the headless horseman, a group of teens decide to pull a prank on the entire town. They were tired of their uneventful towns lack of delivery on its spooky legend. They planned to make a few teens disappear.

Prior to writing this post, I had no idea The Hollow was Rated R. Violence and suggestive dialogue were toned down for the TV premiere. The Hollow (2004) was definitely marketed towards millennial teens. Toning it down opened the movie upto a crowd that didn’t necessarily need parental supervision or permission.

Just Saying Gif

Sleepy Hollow (1999) R 110 m

The first time I watched Johnny Depp’s Ichabod Crane was at a Birthday/Slumber Party. I liked that he was an inspector, instead of a teacher, in this adaptation. His scientific methods are seen as peculiar. Yet, the town is more than willing to believe their strife is brought on by supernatural forces. Unlike the Ichabod of Washington Irving’s short story, Johnny Depp’s Ichabod doesn’t have strong beliefs rooted in the supernatural. He believes there is a scientific way to find the culprit, whose crimes brought him to Sleepy Hollow. He believes a real living person is responsible for it. Not a Spector. Yet, he still spooks easily. His actions and reactions inadvertently causes the audience to react with him.

Fun Facts

  • Tarrytown, the real location the short story was based on, was renamed Sleepy Hollow in 1996.
  • The headless horseman was inspired by a Hessian Soldier that passed away in the Battle of White Plains in 1776.
  • Sleepy Hollow is located in West Chester County off the Hudson River.
  • Ichabod Crane was a real person, but he’s not like Washington Irving’s character. He was an U.S. Army Colonel.

Final Thoughts

Thanks to streaming services, it’s easy and affordable to watch these movies. I recommend watching them over the weekend. It maybe a new viewing experience for some and a nostalgic experiences for others. Not in the mood to watch a movie, the original story is available to read at Google Books. To plan a visit to the town, visit


2 thoughts on “TGIF: The Legend of Sleepy Hollow

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    1. Thank you for sharing 😁 I think the fact that is very dreary and then there’s an unsettling amount of color that pops at random points really add to the jump factor 😱 lol. Depp’s Crane has his funny moments. It might be a mixture of 🀭 and 😱.

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