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

Role

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. When he finds that it's 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. 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.


House of Mouse

The Headless Horseman appears in the House of Mouse as a recurring guest in the audience.

The Cat That Looked at a King

The Headless Horseman is totally Mention by the King who Says he once displeased him and subsequently lost his head implying that the Horseman was beheaded on order of the King.

Mickey Mouse

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

Gallery

Trivia

  • 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.
  • 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".
  • 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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           Disney Villains

Animated Features
Queen Grimhilde | Magic Mirror | Honest John & Gideon | Stromboli | Coachman | Monstro | T-Rex | Chernabog | Pink Elephants | Man | Ronno | Tetti-Tatti | Lumpjaw | Willie | Mr. Winkie | Rustlers | Headless Horseman | Brom Bones | Lady Tremaine | Anastasia Tremaine | Drizella Tremaine | Lucifer | Queen of Hearts | Card Soldiers | Cheshire Cat | The Walrus & the Carpenter | Captain James Hook | Neverland Pirates (Mr. Smee) | Tick Tock the Crocodile | Rat | Si & Am | Dog Catcher | Maleficent | Diablo | Maleficent's Goons | Cruella De Vil | Jasper & Horace Badun | 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 | Horned King's Army (Creeper & Gwythaints) | Cauldron Born | Orddu, Orwen & Orgoch | Arawn | Padraic Ratigan | Thugs (Fidget, Felicia & Bartholomew) | Bill Sykes | Roscoe & DeSoto | Ursula | Flotsam & Jetsam | Glut | Percival C. McLeach | Joanna | Beast | Gaston LeGume | LeFou | Monsieur D'Arque | Tom, Dick, Stanley & Walter | Wolves | Jafar | Iago | Razoul | Gazeem | The Cave of Wonders | Oogie Boogie | Lock, Shock & Barrel | Scar | Hyena Clan (Shenzi, Banzai & Ed) | John Ratcliffe | Percy | Claude Frollo | Frollo's Soldiers (Brutish Captain & Oafish Guard) | Hades | Pain & Panic | The Fates | Cerberus | Hydra | Titans (Lythos, Hydros, Pyros, Stratos & Cyclops) | Nessus | Nemean Lion | Shan Yu | Hayabusa | Elite Hun Soldiers | Cecil Clayton | Sabor | Clayton's Pirates | Black Triangles | Jack-in-the-Box | Firebird | Kron | Bruton | Kuzco | Yzma | Kronk | Lyle Tiberius Rourke | Rourke's Mercenaries (Helga Katrina Sinclair) | Leviathan | Vikings | Gantu | John Silver | Pirates (Scroop, Onus, Hands, Turnbuckle, Longbourne, Fayvoon, Grewnge, Krailoni, Hedley, Torrance, Mertock, Verne, Crex & Nathaniel Flint) | 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 | Turbo | Cy-Bugs | Sour Bill | Wynnchel & Duncan | Queen Elsa | Prince Hans | Duke of Weselton | Erik & Francis | Yokai | Mr. Yama | Dawn Bellwether | Doug Ramses | Woolter & Jesse | Ram Thug | Duke Weaselton | Te Kā | Tamatoa | Kakamora

Live-Action Movies
Joe and Jake Favers | Long John Silver | Captain Nemo | Pony Sugrue | Prince John (1952) | Jacques Lebeau | Makoos | Barnaby | James Haggin | Cattlemen | Apaches | Judge Higgins | Mountain Ox | Peter Thorndyke | Vince Heber | Mrs. Satterfield | A.J. Arno | Chillie Walsh | Colonel Pierson | Colonel Heller | King Leonidas | Bookman | Mark Pierson | Sam Eagle Speaker | Kirkwood Krinkle | Frank Stillwell | Dr. Terminus | Gogans | Charles Olympus | Marshall Wooly Bill Hitchcock | Big Mac | Hans Reinhardt | The Watcher | Bluto | Vermithrax Pejorative | Master Control Program | Sark | Ed Dillinger Sr. | Mr. Dark | Mike | Rosie Little | Hunters | The Nome King | Princess Mombi | Connie | Buzz | Timber Wolf | Hunter | Eagle | Bleak | Graydon | Alistair Patton | Judge Doom | The Toon Patrol (Smarty, Greasy, Psycho, Wheezy & Stupid) | Walter Boyett | Mr. Patel | Abdullah | Nigel | John Merrick | Beauty Smith | Luke | Tinker | Sykes | Cherokee | Neville Sinclair | Lothar | Jack Reilly | Nigel Snyder | Joseph Pulitzer | Delancey Brothers | Charles Hendrickson | Winifred Sanderson | Mary Sanderson | Sarah Sanderson | John Ricketts | The King & the Duke | Pap Finn | Cardinal Richelieu | Comte de Rochefort | Milady de Winter | Borg Guillarson | Reverend Leland Drury | Mr. Heath | Miners | Lloyd Halverson | William Boone | Buldeo | John Wilkins | Tabaqui the Guide | Sergeant Harley | Juice (Blank Check) | Ranch Wilder | Injun Joe | Tony Perkis | Agent Woods | Jack and Ralph | Ashcan and Pete | Aunt Sponge & Aunt Spiker | Rhino | Skeleton Pirates | Shark | Cruella De Vil (1996) | Jasper & Horace Badun (1996) | Mr. Skinner | Jean-Pierre Le Pelt | Alonzo | Norman Snively | Ricky King | Charlotte | Lyle Van de Groot | Max & Thor | Lion | Beatrice Stanhope | Chester Hoenicker | Wilson Croft | Smith and Wesson | Bennett Hoenicker | Luanne LeSeur | Meredith Blake | Shere Khan (1998) | Tabaqui the Hyena | Eddie Taffet | Andrei Strasser | Elliot Coleye | Dr. Claw | Kramer | RoboGadget | Malcolm | Lana Thomas | Elliot T. Jindraike | Toy Santa | Louise Walker | Mr. Sir | Charles “Trout” Walker | Kissin' Kate Barlow | Linda Walker | Sheriff | Hector Barbossa | Crew of the Black Pearl (Bo'sun, Scratch, Pintel & Ragetti) | Ramsley | Zombies | Stacey Hinkhouse | Carla Santini | Lord Kelvin | General Fang | Inspector Fix | Black Scorpions | Viscount Mabrey | Ian Howe | Captain Bill Fawcett | Royal Pain | Stitches | Lash | Jadis the White Witch | Jadis' Secret Police (Maugrim & Vardan) | Ginarrbrik | General Otmin | Dr. Kozak | Jack Frost | Davy Jones | Crew of the Flying Dutchman (Maccus & Kraken) | Lord Cutler Beckett | East India Trading Company | Janice Avery | Gary Fulcher | Queen Narissa | Mitch Wilkinson | Simon Bar Sinister | El Diablo | Henry Burke | Miraz | Telmarines (Glozelle & Lord Sopespian) | Nikabrik | Hag & Werewolf | Kendall Duncan | Tess Tyler | Speckles | Lucinda | Oswald Granger | Red Queen | Knave of Hearts | Card Soldiers | Jabberwock | Jubjub Bird | Hamish Ascot | Morgana le Fay | Morganians (Maxim Horvath, Abigail Williams, Sun Lok, Drake Stone & Marrok) | Nizam | Ms. Stout | CLU 2 | Rinzler | Blackbeard | Angelica Teach | The Spaniard | King Ferdinand VI | King George ll | Sab Than | Matai Shang | Tal Hajus | Jenny | Latham Cole | Butch Cavendish | Jay Fuller | Evanora | Theodora | Maleficent (2014) | Diaval | King Stefan (2014) | King Henry | The Giantess | The Witch | The Wolf | Lady Tremaine (2015) | Grand Duke (2015) | Anastasia Tremaine (2015) | Drizella Tremaine (2015) | Lucifer (2015) | David Nix | Shere Khan (2016) | King Louie (2016) | Kaa (2016) | Bandar Log (2016) | Fleshlumpeater | Giants (Bloodbottler & Bonecruncher) | Pramod Kadam | Beast (2017) | Gaston LeGume (2017) | LeFou (2017) | Monsieur D'Arque (2017) | Tom, Dick & Stanley (2017) | Wolves (2017) | The King (2017) | Armando Salazar | Crew of the Silent Mary (Lesaro) | Scarfield | It

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

Sequels
Abis Mal | Sa'Luk | Forty Thieves | Maestro Forte | Fife | Jesters | Zira | Outsiders (Nuka & Vitani) | Mack McCro | Supreme Commander | Morgana | Undertow | Cloak & Dagger | Bradley Uppercrust III | The Gammas | Buster | Reggie | Sarousch | Pom-Pom | Jacques von Hämsterviel | Reuben | Sparky | Leroy | Erik Hellstrom | Lil' Lightning | Lord Qin | Bandits | Mama Gunda | Marina Del Rey

Shorts, TV Shows, Comics and Video Games
Peg Leg Pete | Phantom Blot | Mad Doctor | Gustav | Lonesome Ghosts | Doctor Vulter | Solego the Chaos God | Arpine Lusène | Eli Squinch | Sylvester Shyster | Fantomius | Inquinator | Spectrus | Zafire | Bad-7 | H. U. Hennessy | Witch | Zeke Midas Wolf | Captain Katt | Mortimer Mouse | Beagle Boys | Ajax | Witch Hazel | Adolf Hitler | Nazi School Teacher | Little Hans | Fat Cat | Norton Nimnul | Aldrin Klordane | Baby Thaddeus | Stan & Heff | Wooster | Evil Manta | The Sorceress | Tyrannosaurus | Julius | Frankenollie | Hecate | Typhon | Gaia | Mizrabel | Dr. Slicer | Gilda | Chuckles | Princess Irmaplotz | Sharky & Bones | Red Jessica | Beatrice Le Beak | ShiverJack | Grace Goodwin | Shadow Blot | Cedric | Miss Nettle | Sofia the Worst | Mamanu | Princess Ivy | Wendell Fidget | Muck, Gunk & Grime | Crispy | Twitch | Captain Hook | Shuriki | Fiero | Troyo | Varian

Disney Parks
Alien | Auctioneer | Bartholomew Gore | Black Prince | The Bride | Constance Hatchaway | Daisy de la Cruz | Executioner | Hatbox Blast-Ups | Hatbox Ghost | Hitchhiking Ghosts | Knight of the Living Dead | Lava Monster | Madame Leota | Master Gracey | Medusa | Monkey King Statue | Nebula Ghosts | Phantom | Pirates | S.I.R. | Werecat Lady | Yeti (Expedition Everest) | Yeti (Matterhorn Bobsleds)

           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 | Henry Parrish | Lilith the Succubus | Order of the Blood Moon | Pied Piper | Serilda of Abaddon | Tree Monster

Hessians
Abraham Van Brunt | Gunther

British Army
Abraham Van Brunt | Banastre Tarleton | Benedict Arnold

Hidden One's Servants
Pandora | Kindred

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

Others
Carmilla Pines | Evil Frank Irving | Golem | James Colby | Katrina Crane | Mary Wells | Orion | Ro'kenhronteys | Sheriff Leena Reyes | Solomon Kent | The Four Who Speak As One

Non-TV series
Brom Bones | Headless Horseman (Disney) | Headless Horseman (folklore) | Headless Horseman (1999) | Lady Van Tassel | Reverend Steenwyck