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25 Crazy Details Behind The Making Of Sleepy Hollow

The story of Sleepy Hollow is a tale that has been around for almost two centuries. The first form of the gothic story was written by author Washington Irving and titled The Legend of Sleepy Hollow. The tale was first included in Irving’s book titled The Sketch Book of Geoffrey Crayon, Gent.

Since then, several filmmakers have adapted his story for feature-length movies and television shows. The first film adaptation came in 1922, over 100 years after the book was written, and was a silent movie titled The Headless Horseman directed by Edward Venturini. One of the most popular productions of Irving’s story came in 1949 and made by Walt Disney Productions. The Adventures of Ichabod and Mr. Toad was an animated movie narrated by Bing Crosby that was a rather comical and family-friendly version of the scary tale.

There have been many other films and TV specials based on the Headless Horseman and Ichabod Crane, including Tim Burton’s adaptation in 1999. The movie was generally well-received and contained an ensemble cast, including Johnny Depp, Christina Ricci, Michael Gambon, and Casper Van Dien.

Even though the movie is nearing its 20th anniversary, Sleepy Hollow still lives up to this day and is a fan-favorite film to watch around Halloween. That being said, there are a lot of behind the scenes facts about the making of Sleepy Hollow that some fans might not be aware of.

Here are the 25 Crazy Details Behind The Making Of Sleepy Hollow.

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25 Johnny Depp Wanted To Use Prosthetics To Look More Accurate To The Book

The character of Ichabod Crane wasn’t originally written as a very attractive person. The Disney movie in 1949 touched upon this by giving the character a giant nose with even bigger ears. The character is also usually very lanky with big feet. That being said, Johnny Depp doesn’t really match this description.

As revealed in the DVD featurette called Behind Sleepy Hollow, Depp mentioned that he would have liked to wear prosthetics to bring the giant nose and ears of Crane to life.

However, ultimately Tim Burton didn’t think they needed the effect. 

24 Tim Burton Specifically Asked To Have the Heads Spin Around

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Even though the decapitations in the movie may have not been very realistic, they looked very Burton-esque. The reason for this was because Tim Burton specifically asked the special effects department to figure out how they could get the heads to spin before they fell to the ground, as revealed in the featurette Behind Sleepy Hollow.

To create the effect, the team had to create mold’s of the victims’ heads to attach to a mechanism which would make the mold spin around. They also created a skeleton from electro-magnets so that they could flip a switch to make the fake body fall limp. 

23 Tim Burton Snuck In Subliminal Messages

Often times horror movies will sneak in subliminal messages to secretly scare the audience. The Exorcist famously did this in 1973, and Tim Burton also did it in 1999 with Sleepy Hollow.

Burton may have not done this as much as other films, but it was revealed in the featurette Behind Sleepy Hollow that Burton snuck an eerie digital effect shot in the scene where the flames in the fireplace burst up behind Steve Waddington’s character. Eagle-eyed viewers will notice several skulls in the flames that were digitally created by altering the Headless Horseman’s skull on a computer. 

22 Johnny Depp Was Inspired By His Love Of Horror Movies

In the featurette Behind Sleepy Hollow, Johnny Depp said that he was inspired to play Ichabod Crane because of his love for horror movie.

“I used to watch all kinds of horror films when I was a little kid. I loved them. I was obsessed with them and I wanted to recreate that classic style of horror film acting,” said Depp.

Depp was no doubt able to achieve this in the role, but it is ironic that his first ever acting credit was actually in the horror movie A Nightmare on Elm Street. 

21 Casper Van Dien Broke His Finger On Set... And kept acting

Brom Van Brunt was one of the unlucky victims of the Headless Horseman, but actor Casper Van Dien was actually injured on set as well. In the featurette Reflections on Sleepy Hollow, he revealed that he actually broke his finger while they were filming one of the first shots of his battle with the Horseman.

Since he was battling with two scythes, his hands weren’t as protected as the actors who got to battle with longer weapons. The actor claims that either an axe or a sword came down during a shot and broke his finger, which immediately turned black. The actor didn’t want his scene to be cut short, so he quickly reset his finger and continued to film his scenes. 

20 Johnny Depp Got To Take Home A Torture Device

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Ichabod Crane is known for having many complicated instruments that he uses to investigate crimes. Johnny Depp, of course, got to play with all of these on set, but he actually got to take home a torture device when the movie was done being filmed.

In one of the courtroom scenes with Christopher Lee, a man can be seen strapped into a device that prevents him from fleeing, which almost looks like some sort of torture device. In the featurette Reflections on Sleepy Hollow, Depp revealed that he fell in love with the contraption and was allowed to take it home with him.

19 Jonny Depp Was Worried The Horses Would Relieve Themselves On Him

One of the more physically demanding stunts that Johnny Depp had to perform happened when his character was dragged through the Western Woods behind two horses.

Depp admitted in the featurette Behind Sleepy Hollow that he wasn’t concerned about being dragged by horses, but he was worried that the animals would relieve themselves while he was strapped in behind them.

It was also revealed that Depp wore bullet-proof armor underneath his costume to protect his body during the journey. Depp also had a quick-release system attached to the rig so that he could detach himself if he needed to during the shoot.

18 They Tried To Create A Sense Of Fear With The Architecture

There is no denying that the buildings in Sleepy Hollow are creepy and no doubt have a Burton-esque vibe to them. Production designer Rick Heinrichs explained in the featurette Behind Sleepy Hollow that, “One of the things we were trying to do was inspire a sense of apprehension in the architecture of the place and there is something wrong here, and there’s a sense of foreboding and fear”.

Most of the architecture present in Tim Burton’s movies often have the same effect on viewers, but the production designers did a great job of effectively creating this for Sleepy Hollow. 

17 Tim Burton Helped Danny Elfman Envision The Score Through Emotion

Danny Elfman is one of the better known composers in Hollywood. He had worked with Burton on several movies prior to Sleepy Hollow, including the films Batman, Edward Scissorhands, and The Nightmare Before Christmas. Elfman even voiced the singing portion of Jack Skellington in 1993.

That being said, it wasn’t much of a surprise when Burton reunited with Elfman for Sleepy Hollow. In the featurette Behind Sleepy Hollow, Elfman stated that he enjoyed working with Burton since the director doesn’t talk in musical terms but instead explains how he wants the music to sound through emotions. 

16 Christopher Walken Wore Colored Contacts And Had Fake Teeth

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Throughout the years, Christopher Walken has become an incredibly well-known actor. He even won an Academy Award in 1979 for his work in The Deer Hunter and was nominated for his role in Catch Me If You Can. The actor had previously worked with Tim Burton on the movie Batman Returns, in which he plays the character Max Shreck.

In Sleepy Hollow, Walken played the Hessian Horseman before he gets his head chopped off.

As revealed in the featurette Behind Sleepy Hollow, in order to give the character a scary look, Walken had to wear bright blue contact lenses and fake teeth that had sharp ends. The disguise probably wasn’t the most comfortable thing for the actor to wear, but it really does make his character look scary.

15 Tim Burton Based The Windmill On A Scene In Frankenstein

Most people who have seen the 1931 movie Frankenstein will remember the iconic windmill scene. In the scene, the villagers attack the Frankenstein monster and end up burning down the entire windmill in the process.

In the featurette Behind Sleepy Hollow, Tim Burton explained that his version of a windmill was based on the scene from Frankenstein. In explaining his reasoning, the director stated, “It’s somewhat symbolic of your mind somehow. I’m not quite sure how or why, but maybe it's just sort of the aimlessly spinning quality that represents my mind.”

14 Ray Park Was The Stuntman Behind The Headless Horseman

Even though Christopher Walken played the Hessian warrior, he didn’t actually play the character for the fighting sequences after the Horseman was decapitated. Instead, the movie employed a stuntman to act out the action sequences - Ray Park.

Park is most known for his Star Wars role of Darth Maul and his role of Snake Eyes in the G.I. Joe movies. The featurette called Behind Sleepy Hollow revealed that Park was filmed while wearing a blue mask, which could easily be digitally removed during post-production to give off the headless appearance. 

13 The Cast Joked That Tim Burton Liked To Cover Johnny Depp In Fake Blood

Throughout Sleepy Hollow, it is apparent that director Tim Burton wanted the movie to have a tongue-in-cheek sort of comedy to it. While being interviewed for the featurette Behind Sleepy Hollow, the cast explained that Tim Burton is actually a very funny person.

Christina Ricci even joked that Burton loved to cover Johnny Depp in fake blood whenever he got the opportunity to.

This actually makes a lot of sense given their working relationship. If it is true, Burton probably had a ball filming Sweeny Todd: The Demon Barber of Fleet Street in 2007. 

12 Tim Burton Was Excited To Work With Johnny Depp For The Third Time

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Johnny Depp and Tim Burton have worked on several movies together. The dynamic duo first teamed up for Edward Scissorhands in 1990 and then again in 1994 for Ed Wood. Depp seems to be Burton’s go-to guy for whimsical characters, and one of the biggest appeals of Sleepy Hollow for Burton was getting to work with Depp again.

This was revealed towards the beginning of the featurette Behind Sleepy Hollowin which Burton had nothing but nice things to say about Depp and expressed how much he enjoyed working with the actor. 

11 The Entire Community Was Built In England

Many productions have to build entire towns, especially if they are a period piece like Sleepy Hollow. The plot of the movie takes place in 1799, which meant that the buildings had to look fairly different than they do today.

Revealed in the featurette Behind Sleepy Hollow, the crew traveled all the way to England to build an entire town that matched the time period of Sleepy Hollow. The set included a covered bridge, a church, a giant windmill, and several other less prominent buildings. Recreating an entire village isn’t unheard of on movie sets, but it is still impressive nonetheless. 

10 Composition, Color, & Movement Were Extremely Important To Tim Burton

Anybody who has seen a Tim Burton movie knows that the director has an incredible eye for detail. Sometimes directors are so unique that you can tell who directed the film from a single frame, and Burton is definitely one of those filmmakers.

In the featurette Behind Sleepy Hollow, several of the crew members praised Burton for his attention to detail.

Johnny Depp even said, “I think Tim first and foremost is an artist. He’s an artist’s approach to every fascite of the film, everything within the frame is of great importance to him.”

9 Christopher Walken Had A Hard Time Riding A Horse

Since Christopher Walken was the Hessian Horseman before he gets decapitated, it was important that he knew how to ride a horse. After all, some of the most important scenes in the movie show the Hessian riding his horse named Daredevil.

That being said, Christopher Walken admitted for the featurette Behind Sleepy Hollow that this was one of the toughest parts of filming Sleepy Hollow. Walken said that even though he had starred in a few Westerns, he didn’t know a lot about horses. Instead, he was afraid of them and was worried that the horses didn’t like him. 

8 The Western Woods Were Built On One Of The Biggest Sound Stages In The World

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Shooting a movie on location versus on a sound stage comes with a great deal of obstacles. While shooting on location can make the movie seem more realistic, filmmakers aren’t in control of everything since they can’t control weather or sounds from nature.

This is why the filmmakers behind Sleepy Hollow decided to film the movie on one of the biggest sound stages in the world. In the featurette Behind Sleepy Hollow, it’s revealed that this allowed the filmmakers to have complete control and change elements of the set at will without having to worry about actual weather. 

7 Incredible Detail Went Into Creating The Decapitated Heads

Each actor who got beheaded in Sleepy Hollow went through the same behind the scenes process. In the featurette Behind Sleepy Hollow, it’s revealed that each actor had to sit and have a plaster cast made of their heads.

After this, the crew made the fake heads come to life by adding silicone paint, fake eyes, and putting hairs into the scalp one by one.

The special effects department would also make acrylic molds of the actors’ teeth for the fake heads. It was a long process to create a head, but the end result looked incredibly realistic. 

6 Johnny Depp Admitted That He Didn’t Have A Lot Of Action Experience In 1999

From jumping atop a moving windmill to being dragged behind live horses, Sleepy Hollow had a lot of action sequences for Johnny Depp to act out. What’s funny, though, is that Depp admitted that he didn’t have a lot of action experience in 1999. In the featurette Behind Sleepy Hollow, he joked that the action sequences were easier than memorizing lines.

That being said, Depp has had a ton of action experience since 1999. Depp played Jack Sparrow in all five Pirates of the Caribbean movies and is currently starring in the Fantastic Beasts and Where to Find Them series.

5 The Coach Chase In The Western Woods Took Three Weeks To Film

The people in charge of building the sets for Sleepy Hollow no doubt had a tough task ahead of them. Not only did they have to build sets for an entire village, but they also had to build the Western Woods where some of the scariest parts of the movie take place.

Even though the set took a while to build, the coach chase within the woods took three whole weeks to film according to the featurette Behind Sleepy Hollow. Not only did the horses have to be trained before the shoot, but the stunts had to be planned out as well.

4 A Lot Of Detail Went Into The Horseman Emerging From The Tree

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According to the featurette Behind Sleepy Hollow, the digital effects department put a lot of detail into the scene where the Horseman emerges from his resting place. First, a shot of a horseman riding in front of a blue screen was filmed, along with a background shot that has the set and the other actors.

The digital effects team then created animated fog, leaves, and dirt that the Headless Horseman would disturb as he rode out from the tree.

Individually, each element looks silly, but when they are combined and digitally meshed together, it creates an incredible scene. 

3 A Mechanical Horse From The Movie National Velvet Was Used

For some of the scenes in Sleepy Hollow, the filmmakers used a mechanical horse to get the desired shot. According to Joss Williams - the special effects supervisor -  in the featurette Behind Sleepy Hollow, the team got a hold of the mechanical horse that was used in the movie National Velvet, which starred Elizabeth Taylor.

While new fur and skin were created for the animal, Williams admitted that there wasn’t anything they could improve upon when it came to the mechanics of the animal. National Velvet had come out 55 years prior to Sleepy Hollow’s release in 1999.

2 Flaming Sticks Were Shot Above The Actors Heads In The Windmill Scene

The windmill in Sleepy Hollow was inspired by the 1931 movie Frankenstein, and this windmill also caught fire like the one in Frankenstein. In order to make this effect look even more realistic, Christina Ricci revealed in the featurette Behind Sleepy Hollow that flaming sticks were shot above the actors heads as they ran away from the windmill.

The crew filled a giant funnel with sticks, hoisted it above the camera, and lit it on fire to create the effect that the windmill was exploding as the characters ran to safety. 

1 Several Of The Cast And Crew Grew Up With The Sleepy Hollow Story

While many people grew up with the story The Legend of Sleepy Hollow or even Disney’s movie from 1949, the cast and crew also grew up with the tale.

Actress Christina Ricci told viewers in the featurette Behind Sleepy Hollow that she was read the creepy tale in nursery school, while Burton explained that the story had inspired him his whole life.

Johnny Depp also said that he grew up with the story. Even though the cast grew up with Sleepy Hollow, it’s safe to say they had no idea what they were getting themselves into since Burton made some significant changes to the source material. 

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Are there any other secrets you know about the making of Sleepy Hollow? Let us know in the comments!

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