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Two Versions of The Legend of Sleepy Hollow


The Legend of Sleepy Hollow is a 1949 Disney cartoon. Sleepy Hollow is a 1999 Francis Ford Coppola film directed by Tim Burton. These are two of the many films based on the Washington Irving story. For many of a certain age The Legend of Sleepy Hollow was their introduction to the Washington Irving tale. Sleepy Hollow falls in the inspired by category, rather than a retelling of the story. The NCAA gave Sleepy Hollow an R rating for graphic violence, gore, and sexuality.[i] This article contains spoilers.

[i] Sleepy Hollow ratings: UK (15), Singapore (NC-16), India (A); a couple of scenes were cut.

The Legend of Sleepy Hollow

Bing Cosby narrates and sings the songs. There is no dialogue the characters’ movements and expressions carry visual side of the story. As with Disney movies the songs move the story. Jud Conlon’s Rhythmaires are the chorus. Other voices are Billy Bletcher, Pinto Colvig, and Clarence Nash.

Ichabod Crane, the new school teacher, ambles into town. He is tall and thin. He has his long nose stuck in a book. Brom Bones, the self-appointed leader of the local young men, is handsome and muscular. Katrina Van Tassel is a beautiful woman. She is also the only child of Baltus van Tassel, the richest man in town. Katrina’s beauty and her father’s wealth attract Ichabod. Marrying Katrina would mean a life of luxury for Ichabod. Every eligible man would like to marry Katrina. This set up a rivalry between Brom Bones and Ichabod Crane. A combination of luck and wits give Ichabod a decisive win in their first encounter. The next chance for Brom to regain the advantage was the van Tassel Halloween party.

At the van Tassel party Ichabod is again winning as Brom’s tricks backfire. Then Brom notices Ichabod is superstitious. After the music and dancing people tell ghost stories. Brom tells a story, in song, about The Headless Horseman. Katrina and the others took it as good fun. The story scares Ichabod. This mixture of fun and fright is a foretaste of what is to come.

Ichabod is riding home on a pathetic excuse for a horse. The road is through a wooded area and includes a graveyard. Ichabod is whistling past the graveyard. His horse would rather rest than walk. A toad seems to be croaking “Ichabod”. What appears to be a ghost is really two fireflies in the hollow of a dead tree. Ichabod hears hoofbeats and realizes his horse is not walking. He sees the “hoofbeats” are just cattails thumping on a log. Ichabod and his horse laugh at the situation. A screeching laugh stops their laughter. The headless horseman is in the distance. A frightening and comical chase ensues.

The film allows for multiple interpretations. This can take the edge off the fright for sensitive viewers.

Sleepy Hollow

The opening scene leaves no doubt there is a headless horseman taking heads. It’s 1799 and Ichabod Crane (Johnny Depp) is a constable in New York City. He wants to bring criminology into the 19th century. His superiors consider him a nuisance. The Burgomaster (Christopher Lee) sends him upstate to investigate a series of decapitations in a hamlet named Sleepy Hollow. The other option was to throw him in jail. The Burgomaster’s final words to Ichabod are “Remember it is you, Ichabod Crane, who is now put to the test.”

Ichabod finds out the heads are all missing when he meets the prominent men of Sleepy Hollow. The locals believe it’s the work of the ghost of a Hessian Horseman (Christopher Walken). Ichabod dismisses the belief and is surprised the educated people in the town believe the legend. Young Masbath (Marc Pickering), whose father (Mark Spalding) was one of the Horseman’s victims, offers his services to Ichabod. Young Masbath is about 15. Katrina Van Tassel (Christina Ricci) and Ichabod have a mutual attraction. Brom Van Brunt (Casper Van Dien) pulls a prank on Ichabod. The prank has some elements of The Legend of Sleepy Hollow. There is no love triangle. The story’s focus is on solving the mystery and the relationship between Ichabod and Katrina. Their relationship changes with the story’s flow.

Ichabod’s skepticism falls to extraordinary proof. Ichabod doesn’t give up his belief the horseman is guided by a living person. There is a flashback to Ichabod’s childhood. The flashback has Sam Fior as Young Ichabod with Lisa Maria as Ichabod’s mother and Peter Guinness as Ichabod’s father, Lord Crane. The scene is one of many scenes reminiscent of the horror films of the 1960s.[i]

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The flashback to his childhood can be interpreted a couple of ways. Is it stylistic or an accurate recounting of his childhood? Does he dismiss those memories? Did the events account for Ichabod’s impatience with superstition?

Ichabod is quirky. He is sometimes brave and sometimes skittery. He faints 5 times in the movie.[ii] His mood swings provide comic relief. Young Masbath is a stoic and reliable character. He goes with Ichabod when none of the men would. Katrina Van Tassel is a complicated character.

Many of the townspeople have dark secrets. Without the Headless Horseman the stories could make for an 18th century soap opera.[iii] The story arc ties these secrets together. This makes for a complicated, yet easy to follow, narrative.

There are armed encounters with the Horseman. The final chase scene is long and complex. The chase scene has some of the elements of Disney’s The Legend of Sleepy Hollow.

Sleepy Hollow is not a movie for sensitive viewers. Anyone who finds The Legend of Sleepy Hollow frightening should probably avoid Sleepy Hollow.[iv]

[i] Sleepy Hollow (1999) - Trivia - IMDb, Christopher Lee was a star in many of the horror films produced by Hammer Film Productions. Hammer was famous for horror film set in previous centuries.

[ii] Sleepy Hollow (1999) - Trivia - IMDb.

[iii] “”soap Opera” is a term given to continuing television shows that deal with the interactions, often seedy, interactions.

[iv] There are scenes outside of the violence and gore that some may find distasteful


This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2021 Robert Sacchi

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