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The Headless Horseman is the main antagonist of The Legend of Sleepy Hollow; the second half of Disney's 11th full-length animated feature film, The Adventures of Ichabod and Mr. Toad.

The Legend of Sleepy Hollow

Brom Bones tells Ichabod Crane the story of the Headless Horseman, who lost his head long ago 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. When he finds that it's only cattails bumping on a log, Ichabod and his horse hysterically laugh but suddenly stop as another 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. 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 all but dismissed, as the good townsfolk of Sleepy Hollow know that he must have been spirited away by the Headless Horseman himself.

Trivia

  • It is never explicitly 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.
  • In many early versions of the Haunted Mansion, the Headless Horseman was to be a focal point of the attraction's graveyard climax.
  • A portrait of the Headless Horseman can be see in the video game, Epic Mickey; in Lonesome Manor's library.
  • The Headless Horseman is actually one of the very few Disney Villains to actually "win" rather than being defeated at the end of his/her film.
  • 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.


 
Sleepy Hollow Villains


Main
Demons | Four Horsemen of the Apocalypse | Headless Horseman's Head | Hidden One | Abraham Van Brunt | Henry Parrish | Malcolm Dreyfuss | Moloch | Pandora


Moloch's Servants & Horsemen
Ancitif | Andy Brooks | Conquest | Famine | Gina Lambert | Abraham Van Brunt | Hellfire Club | Henry Parrish | Lilith the Succubus | Order of the Blood Moon | Pied Piper | Serilda of Abaddon | Tree Monster

Hessians
Armin & Hagen | Carlton | Abraham Van Brunt | Gunther


British Army
Abraham Van Brunt | Banastre Tarleton | Benedict Arnold | William Howe | Hellfire Club | Marcus Collins


Hidden One's Servants
Abyzou | Atticus Nevins | Dr. Japeth Leeds | Marcus Collins | Pandora | Kindred | Yao-Quai


Dreyfuss Enterprises
Abraham Van Brunt | Logan MacDonald | Helen Donovan | Jobe | Henry Parrish | Malcolm Dreyfuss


Others
Carmilla Pines | Colonel Sutton | Erza Mills | Evil Frank Irving | Golem | Gorgon | James Colby | Katrina Crane | Mary Wells | Orion | Randall Martin | Reaver | Ro'kenhronteys | Sheriff Leena Reyes | Solomon Kent | The Four Who Speak As One |


Non-TV series
Brom Bones | Brom Van Brunt | Headless Horseman | Headless Horseman (Disney) | Headless Horseman (folklore) | Headless Horseman (Sleepy Hollow 1999) | Lady Van Tassel


Disney Villains

Animated Features
Queen Grimhilde | Magic Mirror | Honest John & Gideon | Stromboli | Coachman | Coachman's Minions | Monstro | T-Rex | Chernabog | Ringmaster | Pink Elephants | Ronno | Man (Bambi) | Tetti-Tatti | Lumpjaw | Willie | Mr. Winkie | Brom Bones | Rustlers | Headless Horseman | Lady Tremaine | Ugly Stepsisters (Drizella & Anastasia) | Lucifer | Queen of Hearts | Card Soldiers | The Walrus & the Carpenter | Captain Hook | Mr. Smee | Neverland Pirates | Si & Am | Maleficent | Diablo the Crow | Maleficent's Goons | Cruella De Vil | Jasper & Horace | Madam Mim | Shere Khan | Kaa | King Louie | Bandar Log | Edgar Balthazar | Prince John | Sheriff of Nottingham | Sir Hiss | Captain Crocodile | Rhino Guards | Wolf Arrowmen | Trigger & Nutsy | Heffalumps & Woozles | Madame Medusa | Mr. Snoops | Brutus & Nero | Amos Slade | Chief | Horned King | Arawn | Creeper | Cauldron Born | Horned King's Guards | Gwythaints | Orddu, Orwen & Orgoch | Padraic Ratigan | Fidget | Felicia | Thugs | Bartholomew | Bill Sykes | Roscoe & DeSoto | Ursula | Flotsam & Jetsam | Glut | Percival C. McLeach | Joanna | Gaston Legume | LeFou | Monsieur D'Arque | Gaston's Buddies | Jafar | Iago | Razoul | Gazeem | Oogie Boogie | Lock, Shock & Barrel | Scar | Shenzi, Banzai & Ed | Hyena Clan | John Ratcliffe | Claude Frollo | Brutish & Oafish Guards | Frollo's Soldiers | Hades | Pain & Panic | Cerberus | Hydra | Titans (Lythos, Hydros, Pyros, Stratos & Cyclops) | Nessus | Nemean Lion | Minotaur | Shan Yu | Hayabusa | Elite Hun Soldiers | Cecil Clayton | Sabor | Clayton's Pirates | Jack-in-the-Box | Snooty Flamingos | Firebird | Kron | Bruton | Yzma | Kronk | Lyle Tiberius Rourke | Helga Katrina Sinclair | Rourke's Soldiers | Leviathan | Gantu | John Silver | Scroop | Onus | Hands | Turnbuckle | Longbourne | Fayvoon | Grewnge | Krailoni | Hedley | Torrance | Mertock | Verne | Crex | Nathaniel Flint | Flint's Pirates | Alameda Slim | Rico | The Willies | Mr. Wesley | DOR-15 | Mike Yagoobian | Dr. Calico | Dr. Facilier | Lawrence | Facilier's Shadow | Friends on the Other Side | Mother Gothel | Stabbington Brothers | King Candy | Cy-Bugs | Sour Bill | Wynnchel & Duncan | Prince Hans | Duke of Weselton | Duke of Weselton's Bodyguards | Yokai | Mr. Yama | Dawn Bellwether | Doug Ramses | Woolter & Jesse | Ram Thug | Duke Weaselton | Te Kā | Tamatoa | Kakamora

Live-Action Movies
Long John Silver | Captain Nemo | Giant Squid | Pony Sugrue | Prince John (1952) | Barnaby | Peter Thorndyke | The Bookman | King Leonidas | Colonel Heller | Dr. Terminus | The Gogans | Charles Olympus | Bluto | Vermithrax Pejorative | Master Control Program | Sark | Ed Dillinger Sr. | Mr. Dark | Nome King | Princess Mombi | Judge Doom | Toon Patrol (Smarty, Greasy, Psycho, Wheezy & Stupid) | Abdullah | Patel | Nigel (Cheetah) | Neville Sinclair | Lothar | Coach Jack Reilly | Warden Nigel Snyder | Josepg Pulitzer | Delancey Brothers | Dr. Charles Hendrickson | Winifred Sanderson | Mary Sanderson | Sarah Sanderson | John Ricketts | The King and the Duke | Pap Finn | William Boone | Buldeo | John Wilkins | Tabaqui | Sergeant Harley | Juice (Blank Check) | Ranch Wilder | Injun Joe | Tony Perkis | Agent Woods | Aunt Sponge & Aunt Spiker | Rhino | Skeleton Pirates | Shark | Cruella De Vil (1996) | Alonzo | Mr. Skinner | Jean-Pierre Le Pelt | Norman Snively | Ricky King | Charlotte (Jungle 2 Jungle) | Lyle Van de Groot | Max & Thor | Beatrice Stanhope | Wilson Croft | Luanne LeSeur | Meredith Blake | Eddie Taffet | Andrei Strasser | Dr. Elliot Coleye | Dr. Claw | Kramer | RoboGadget | Lana Thomas | Principal Elliot T. Jindraike | Toy Santa | Warden Walker | Mr. Sir | Charles “Trout” Walker | Kissin' Kate Barlow | Ramsley | Stacey Hinkhouse | Carla Santini | Lord Kelvin | General Fang | Inspector Fix | Black Scorpions | Viscount Mabrey | Ian Howe | Royal Pain | Stitches | Jadis the White Witch | Maugrim | Ginarrbrik | General Otmin | Vardan | Dr. Kozak | Jack Frost | Janice Avery | Gary Fulcher | Queen Narissa | Mitch Wilkinson | Simon Bar Sinister | El Diablo | Kendall Duncan | Tess Tyler | Speckles | Miraz | Sospespian | Glozelle | Nikabrik | Hag & Werewolf | Lucinda | Oswald Granger | The Red Queen | The Knave of Hearts | Hamish Ascot | The Jabberwock | Jubjub Bird | Nizam | Morgana le Fay | Maxim Horvath | Abigail Williams | Sun Lok | Drake Stone | Ms. Stout | CLU 2 | Rinzler | Sab Than | Matai Shang | Tal Hajus | Jenny | Latham Cole | Butch Cavendish | Jay Fuller | Evanora | Theodora | King Stefan | King Henry | Taylor Dean | The Giantess | The Witch | The Wolf | Lady Tremaine (2015) | The Grand Duke (2015) | David Nix | Shere Khan (2016) | King Louie (2016) | Kaa (2016) | Bandar Log (2016) | Fleshlumpeater | Bloodbottler | Giants | Gaston Legume (2017) | LeFou (2017) | Monsieur D'Arque (2017) | Gaston's Buddies (2017) | The King (2017)

Other Animated Movies
Br'er Fox & Br'er Bear | Elmo St. Peters | Giant Magnet | Evil Clown | Merlock | Guy Graham | Phillium Benedict | Fenwick | Kojak | Ivan Krank | Von Talon | Cufflingk & Underlingk | Kazar | The Supervisor | Mr. Whiskers | Were-Rat | Shelley | Colossus | Nassor | Toshiaki | Mr. Burgermeister | Ripslinger | Cad Spinner | Bog King | Roland

Pixar
Sid Phillips | Hopper | Thumper | Stinky Pete | Al McWhiggin | Emperor Zurg | Zurg Empire (Zurg Bots, Warp Darkmatter, Hornets, Brain Pods & Grubs) | Henry J. Waternoose III | Randall Boggs | Jeff Fungus | Syndrome | Mirage | Omnidroids | Underminer | Bomb Voyage | Chick Hicks | Chef Skinner | AUTO | GO-4 | Charles Muntz | Alpha | Beta & Gamma | Lotso | Lotso's Gang (Ken, Big Baby, Stretch, Chunk, Sparks, Twitch & Monkey) | Miles Axlerod | Zundapp | Grem | Acer | Mor'du | Johnny Worthington III | Chet Alexander | Roar Omega Roar | Thunderclap | Pterodactyls | Bubbha | Velociraptors | Sterling | Jackson Storm

Sequels
Abis Mal | Sa'Luk | Forty Thieves | Forte | Jesters | Zira | Nuka | Vitani | Outsiders | Morgana | Undertow | Cloak & Dagger | Bradley Uppercrust III | Tank | The Gammas | Buster | Reggie | Sarousch | Pom-Pom | Jacques von Hämsterviel | Reuben | Leroy | Porcupine (Disney)| Erik Hellstrom | Lil' Lightning | Lord Qin | Atka | Dixie | Mama Gunda | Uto & Kago | Marina Del Rey

Shorts and Comics
Peg Leg Pete | Kat Nipp | Phantom Blot | Mad Doctor | H. U. Hennessy | Big Bad Wolf | Captain Katt | Mortimer Mouse | Ajax the Gorilla | Beagle Boys | Flintheart Glomgold | Magica De Spell | Grace Goodwin