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Villain Overview

Yaaaah-ha-ha-ha-ha-haaaa!
~ The Headless Horseman's evil laugh.

The Headless Horseman is the main antagonist of Disney's The Legend of Sleepy Hollow (which is based on the 1820 short story of the same name by the late Washington Irving); the second half of Disney's 11th full-length animated feature film The Adventures of Ichabod and Mr. Toad.

The Headless Horseman is voiced by the late Billy Bletcher.

Biography

Through the song, Brom Bones tells Ichabod Crane the story of the Headless Horseman, who was beheaded during the Revolutionary War. Every Halloween night he rides in Sleepy Hollow looking for a new head. The best way to escape him is to cross the bridge, as the Horseman's dark powers are limited only to the woods.

That very night, Ichabod rides home alone and keeps imagining that he is being followed as he hears noises while he slowly traverses the forest atop his horse.

The Horseman chases after Ichabod.

When he finds that it is only cattails bumping on a log, Ichabod and his horse hysterically laugh but suddenly stop as another sinister laugh joins them. They both slowly turn around to find the Headless Horseman about to attack them.

He gives chase, laughing all the while. When Ichabod momentarily is trapped on the Horseman's own black steed, he looks down the Horseman's neck to find nothing but evil hollow laughter.

Once you cross that bridge, my friends, the ghost is through, his power ends.
~ Ichabod remembers Bron's song's lyrics to stay safe from the Horseman.

The Horseman throws his pumpkin head at Ichabod, possibly killing him.

Ichabod runs for the bridge and barely manages to make it across. As Ichabod turns around, he screams as the the black horse rears up and the Headless Horseman throws his head (a Jack o'Lantern set on fire) right at him.

The very next morning Ichabod's hat was found next to a shattered pumpkin, but Ichabod had vanished. Rumors about Ichabod still alive and married to a wealthy widow in a distant county are dismissed, as the good townsfolk of Sleepy Hollow know that he must have been spirited away by the Headless Horseman himself.

Other Media

House of Mouse

Mickey Mouse talking to the Headless Horseman in House of Mouse.

The Headless Horseman regularly appeared in House of Mouse as a recurring guest in the audience, though rarely since he can't speak, thus he's moreso used for one-time gags such as being featured in a Lost & Found commercial where he finds his pumpkin head, being part of Von Drake's song when counting down Disney characters and where they sit, being asked to lend his blade for a moment and, most commonly, scaring Ichabod.

He was naturally allied among the villains during the takeover of the House of Mouse.

The Revenge of the Headless Horseman

The Headless Horseman appeared as the main antagonist in the now-defunct attraction of the same name at Hong Kong Disneyland. When a traveling circus claims that they have found the Horseman's head and are displaying it, the Horseman returns to slaughter and behead them all and reclaim what is his.

The Scariest Story Ever: A Mickey Mouse Halloween Spooktacular

The Headless Horseman makes a cameo in the special The Scariest Story Ever: A Mickey Mouse Halloween Spooktacular where while trick or treating Goofy sees him take the place of a statue and give his iconic laugh much to his horror.

Epic Mickey

A portrait of the Headless Horseman can be see in the videogame Epic Mickey in Lonesome Manor's library.

Trivia

Ichabod looks down the Horseman's clothes.

  • It is inexplicably revealed whether or not the Headless Horseman was a real phantom or Brom Bones in disguise (as it was heavily implied in the book that the movie was based on). However, there are some suggestions that the Horseman was indeed an actual phantom, though from what was shown of Ichabod's fearful imagination beforehand, some of these things may have been imagined by him:
    • Ichabod had looked inside his cloak, revealing nothing to be there.
    • Brom's horse did not have red eyes and a black mane like the Horseman's did.
    • Brom needed a saddle, reins, and a bridle to ride his horse, while the Horseman apparently didn't. His implied spiritual nature would likely allow him to remain on his horse without any real support.
    • The Horseman appeared to be slightly skinnier than Brom.
    • The Horseman's horse jumped high over a cliff, which no other horse could do.
  • In many early versions of the Haunted Mansion, the Headless Horseman was to be a focal point of the attraction's graveyard climax.
  • The Headless Horseman is actually one of the very few Disney Villains to actually "win".
  • Despite making a small appearance, the Headless Horseman is considered one of the darkest and most disturbing Disney villains.
  • The Headless Horseman appeared on the Wonderful World of Disney the same Sunday night that The Beatles were on The Ed Sullivan Show.

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Other Animated Movies
Br'er Fox & Br'er Bear | Giant Magnet | Evil Clown | Judge Doom | Toon Patrol (Smartass, Greasy, Psycho, Wheezy & Stupid) | Merlock | Dijon | Aunt Sponge | Aunt Spiker | Rhino | Skeleton Pirates | Shark | Bill Bluff | BluffCo Industries (Guy Graham, Bob & Bluff Agents) | Phillium Benedict | Anti-Recess Legion (Kojak, Fenwick, Anti-Recess Agents, Anti-Recess Ninjas, Anti-Recess Scientists, Agent Henderson, Agent Smithson, Agent Underville, Agent Franklin, Agent Morrisey, Agent Goodman, Dr. Rosenthal, Dr. Lazenby & Dr. Steinheimer) | Gelman | Gloomius Maximus | Dr. Ivan Krank | Clarabelle Cow | Von Talon | Cufflingk and Underlingk | Kazar | Wildebeests (Blag) | Scab and Scraw | Vidia | Jacob Marley | Old Joe | Supervisor | Mr. Whiskers | Shelley | Were-Rat | Sea Monkeys | Mr. Burgermeister | Ripslinger | Ned and Zed | Zarina

Direct-to-video/Disneytoon Studios Sequels/Disney+ Originals
Abis Mal | Abis Mal's Thugs | Sa'Luk | Forty Thieves | Maestro Forte | Jesters | Zira | Outsiders (Nuka & Vitani) | Mack McCro | Jim Bob | Supreme Commander | Morgana | Undertow | Cloak & Dagger | Bradley Uppercrust III | The Gammas | Buster | Sarousch | Pom-Pom | Jacques von Hämsterviel | Erik Hellstrom | Ashton Carnaby | Edgar Volgud | Krakken | Lil' Lightning | Bandits | Mama Gunda | Uto & Kago | Marina Del Rey | Cad Spinner | Orson | Sweet Pete | Captain Putty | Jimmy the Polar Bear | Bob the Viking | Bjornson the Cheesemonger

Animated Television
Flintheart Glomgold | Magica De Spell | Beagle Boys | Ma Beagle | Fat Cat | Fat Cat's Gang | Norton Nimnul | Aldrin Klordane | Baby Thaddeus | Ratso Ratzkiwatzki | Mozenrath | Mirage | Mechanicles | The Collector (Bonkers) | Cousin Zeke | Kent Powers | Henry Villanova | The Green-Eyed Monster of Jealousy | Ivy DeVil | Judge Dimsdale De Vil | Gelman | Tad White | James Stone | Dr. Slicer | Gilda | Mayor Phillip Fitzhugh | SAL 3000 | DeSilvo | Earl Raymond | Al Roker | Chuckles | Huntsman | Huntsgirl | Dark Dragon | Heinz Doofenshmirtz | Norm | Vanessa Doofenshmirtz | Lucius Heinous VII | Brad Buttowski | Brianna Buttowski | Harold Buttowski | Brick Bristol | Bill Cipher | Li'l Gideon | Stanley Pines | Abraham Kane | Donald Duck's Raw Anger | Jordan Buttsquat | Suzi | Lord Dominator | Lord Hater | Commander Peepers | Rippen | Toffee | Ludo | Meteora Butterfly | Mina Loveberry | Solaria Butterfly | Tom Lucitor | Commander Heist | Lazlo | Zhan Tiri | Lady Caine | Varian | King Edmund | Cassandra | Bradford Buzzard | Flintheart Glomgold (2017) | Magica De Spell (2017) | General Lunaris | Obake | Diane Amara | Noodle Burger Boy | Globby | Chris | High Voltage | Baron Von Steamer | Momakase | Mel Meyer | Mad Jacks | Trina | Hardlight | Chip Whistler | Gwendolyn Zapp | Hunter De Vil | Cuddles | Clarissa Corgi | Portia Poodle | Canal Crew (Fergus, Sid Squirrel & Big Fee) | Bessie the Cornish Cow | King Andrias | Captain Grime | Sasha Waybright | The Core | King Aldrich | Emperor Belos | Hunter | Lilith Clawthorne | The Collector (The Owl House) | Infinity Ultron | The Ghost Council | The Chairman | The Barrister Ghosts

Live-Action TV
Miss Hendra | Victoria Kayne | Gorog | Dominic | Evil Alex | Dr. Evilini | The Mummy | Ronald Longcape Jr. | Penelope | Kaita | Lanny Parker | King Kalakai/Yamakoshi | Zadoc | Farhog the Fierce | Lexi Reed | Susan Skidmore | Sally Jensen | Sensei Ty | Rhoda Chesterfield | Creepy Connie Thompson | Darla Shannon | Madeline | Bryn Beitbart | McD | Brooke | Victor Krane | Douglas Davenport | Marcus Davenport | Giselle Vickers | Taylor Krane | Sebastian Krane | Principal Perry | Ludmila Ferró | Jade & Matias LaFontaine | Gregorio Casal | Gery López | Priscila Ferró | Clément Galán | Esmeralda Di Pietro | Milton Vinicius | Crash Bernstein | Helga Rooney | Missy Bradford | Dawn Buckets | Laughy Cat | Brad & Brads | Agent Johnson | Brett Willis | Zane Willis | Mitch Bishop | Janet Smythe | Sebastian | Cyd Ripley | Gladys | Hazel Swearengen | Dr. Sharon Chen | Ámbar Smith | Sharon Benson | Rey Gutiérrez | Benicio | Red Sharks (Gary López) | Emilia | Ramiro Ponce | Matteo Balsano

Literature
King Nicholas

Video Games
Mizrabel | Oswald Gardner | Admiral Evar | Cogs | Herbert P. Bear | Atticus Thorn | Foxy Loxy | Goosey Loosey | Jolly Roger | Shadow Blot | False Shadow Blot

Shorts
Peg Leg Pete | Kat Nipp | Old Man Tree | Skeletons | Grim Reaper | Mad Doctor | Demon Cats | Gustav the Giant | Lonesome Ghosts | H. U. Hennessy | Witch | Pluto's Devil | Ben Buzzard | Zeke Midas Wolf | Izzy Wolf | The Three Little Wolves | Boogeymen | Captain Katt | Mortimer Mouse | Butch the Bulldog | Foxy Loxy | Ajax Gorilla | Beppo Gorilla | Witch Hazel | Adolf Hitler | Nazi School Teacher | Little Hans | Julius | Dr. Frankenollie | Grace Goodwin | Molly

Comics
Phantom Blot | Trudy Van Tubb | Doctor Vulter | Solego the Chaos God | Arpine Lusène | Monsieur Molay | Azure Blue | Lawyer Sharky | Eli Squinch | Sylvester Shyster | Fantomius | Inquinator | Spectrus | Raghor | Zafire | Newton | The Raider | Emil Eagle | Sr. X | X-1, X-2 and X-3 | Professor Nefarious | Fliplip, Sidney and Armadillo | Neighbor Jones | Anacleto Faina | Anacleto Mitragli | Beagle Boys | Ottoperotto

Manga
Ansem, Seeker of Darkness | Xemnas

Attractions
Alien | Lava Monster | Mara | Mad Hatter | Nebula Ghosts | Professor J.T. Wu | S.I.R. | Yeti (Expedition Everest) | Yeti (Matterhorn Bobsleds)

See Also
101 Dalmatians Villains | 2010 Marvel Animated Universe Villains | 20th Century Studios Villains | A Twisted Tale Villains | Air Bud Villains | Aladdin Villains | Alice in Wonderland Villains | Amblin Entertainment Villains | American Dragon Jake Long Villains | Amphibia Villains | Artemis Fowl Villains | Atlantis Villains | Beauty and the Beast Villains | Big Hero 6 Villains | Buena Vista International Villains | Buzz Lightyear of Star Command Villains | Camp Lakebottom Villains | Cars Villains | Chip 'N' Dale: Rescue Rangers Villains | Cinderella Villains | Club Penguin Villains | Darkwing Duck Villains | Descendants Villains | Disney Chills Villains | Disney Infinity Villains | DuckTales Villains | Fantasia Villains | Fillmore! Villains | Frankenstein Villains | Frozen Villains | FX Villains | Gargoyles Villains | Gravity Falls Villains | Halloweentown Villains | Hamilton Villains | Haunted Mansion Villains | Hercules Villains | Ice Age Villains | Incredibles Villains | Jack London Villains | Jerry Bruckheimer Villains | Jimmy Two-Shoes Villains | Kim Possible Villains | Kingdom Hearts Villains | Lilo & Stitch Villains | Little Einsteins Villains | Lucasfilm Villains | Marvel Animated Movie Universe Villains | Marvel Cinematic Universe Villains | Medfield College Villains | Mighty Ducks Villains | Milo Murphy's Law Villains | Monsters, Inc. Villains | Mulan Villains | Muppet Villains | Narnia Villains | New Mutants Villains | Once Upon A Time Villains | Peter Pan Villains | Phineas and Ferb Villains | Pinocchio Villains | Pirates of the Caribbean Villains | Pixar Villains | Quack Pack Villains | Randy Cunningham Villains | Recess Villains | Robin Hood Villains | Sherlock Holmes Villains | Sleeping Beauty Villains | Snow White Villains | Sofia the First Villains | Star Wars Villains | Star vs. the Forces of Evil Villains | Super Robot Monkey Team Hyperforce Go! Villains | Tangled Villains | Tarzan Villains | The Emperor's New Groove Villains | The Ghost and Molly McGee Villains | The Hunchback of Notre Dame Villains | The Jungle Book Villains | The Lion King Villains | The Little Mermaid Villains | The Owl House Villains | The Princess and the Frog Villains | The Princess Diaries Villains | The Proud Family Villains | Tim Burton Villains | Toy Story Villains | Treasure Planet Villains | Tron Villains | Wander Over Yonder Villains | Winnie the Pooh Villains | Wreck-It Ralph Villains | X-Men Movie Villains | Yin Yang Yo! Villains | Zootopia Villains

            Sleepy Hollow logo.png Villains

Headless Horseman and Variants
Headless Horseman (Disney | 1999 | PorchLight | 2007 | Sleepy Hollow)

Demons
Moloch | Ancitif | Ro'kenhronteys | Banastre Tarleton | Tree Monster | Lilith the Succubus | The Devil

Four Horsemen of the Apocalypse
Death | War | Conquest | Famine

Hessians
Gunther

Order of the Blood Moon
Serilda of Abaddon

The Four Who Speak As One
Katrina Crane

British Army
Abraham von Brunt | Banastre Tarleton | Benedict Arnold | William Howe

Dreyfuss Enterprises
Malcolm Dreyfuss | Abraham von Brunt | Logan MacDonald | Helen Donovan | Jobe

Others
Brom Bones | Lady Van Tassel | Reverend Steenwyck | Satan | Hidden One | Pandora | Kindred | Henry Parrish | Andy Brooks | Headless Horseman's Head | Gina Lambert | Pied Piper | Atticus Nevins | Carmilla Pines | Evil Frank Irving | Golem | James Colby | Leena Reyes | Mary Wells | Orion | Solomon Kent

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