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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 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.

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.
           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

           Disney Villains

Animated Features
Queen Grimhilde | Magic Mirror | Honest John & Gideon | Stromboli | Coachman | Coachman's Minions | 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 | The Walrus & the Carpenter | James Hook | Mr. Smee | Neverland Pirates | Si & Am | Rat | Maleficent | Diablo | 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 Army | 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 | The Cave of Wonders | Oogie Boogie | Lock, Shock & Barrel | Scar | Hyena Clan (Shenzi, Banzai & Ed) | John Ratcliffe | Claude Frollo | Brutish and Oafish Guards | Frollo's Soldiers | 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 | Helga Katrina Sinclair | Rourke's Mercenaries | Leviathan | Gantu | John Silver | Scroop | Onus | Hands | Turnbuckle | Longbourne | Fayvoon | Grewnge | Krailoni | Hedley | Torrance | Mertock | Verne | Crex | Nathaniel Flint | Nathaniel 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 | Wreck-It Ralph | Turbo | Cy-Bugs | Sour Bill | Wynnchel & Duncan | Prince Hans | Duke of Weselton | Duke of Weselton's Bodyguards | Robert Callaghan | 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) | Jacques Lebeau | Barnaby | Comanche | Peter Thorndyke | A.J. Arno | Cookie | Colonel Pierson | Colonel Heller | King Leonidas | Bookman | Krinkle | Dr. Terminus | Gogans | Charles Olympus | Dr. Hans Reinhardt | The Watcher | Bluto | Vermithrax Pejorative | Master Control Program | Sark | Ed Dillinger Sr. | Mr. Dark | Mike | Nome King | Princess Mombi | Connie | Hunter | Judge Doom | Toon Patrol (Smarty, Greasy, Psycho, Wheezy & Stupid) | Mr. Patel | Abdullah | Nigel | Beauty Smith | Neville Sinclair | Lothar | Jack Reilly | Nigel Snyder | Joseph Pulitzer | Delancey Brothers | Charles Hendrickson | Winifred Sanderson | Mary Sanderson | Sarah Sanderson | John Ricketts | The King and the Duke | Pap Finn | Cardinal Richelieu | Comte de Rochefort | Milady de Winter | Reverend Leland Drury | 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 (1996) | Alonzo | Mr. Skinner | Jean-Pierre Le Pelt | Norman Snively | Ricky King | Charlotte | Lyle Van de Groot | Max & Thor | Lion | Beatrice Stanhope | Wilson Croft | 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 | Ramsley | Stacey Hinkhouse | Carla Santini | Lord Kelvin | General Fang | Inspector Fix | Black Scorpions | Viscount Mabrey | Ian Howe | Royal Pain | Stitches | Jadis the White Witch | Jadis' Secret Police (Maugrim & Vardan) | Ginarrbrik | General Otmin | Dr. Kozak | Jack Frost | 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 | Hamish Ascot | Jabberwock | Jubjub Bird | Morgana le Fay | Morganians (Maxim Horvath, Abigail Williams, Sun Lok, Drake Stone & Marrok) | Nizam | Ms. Stout | CLU 2 | Rinzler | Kali | Sab Than | Matai Shang | Tal Hajus | Jenny | Latham Cole | Butch Cavendish | Jay Fuller | Evanora | Theodora | Maleficent (2014) | Diaval | King Stefan (2014) | King Henry | Taylor Dean | 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 | Bloodbottler | Giants | Pramod Kadam | 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 | Dijon | Guy Graham | Phillium Benedict | Fenwick | Kojak | Ivan Krank | Von Talon | Cufflingk & Underlingk | Kazar | Vidia | Supervisor | Mr. Whiskers | Were-Rat | Shelley | Colossus | Nassor | Toshiaki | Mr. Burgermeister | Ripslinger | Cad Spinner | Zarina | Bog King | Roland

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

Shorts and Comics
Peg Leg Pete | Phantom Blot | Mad Doctor | Gustav | Lonesome Ghosts | H. U. Hennessy | Zeke Midas Wolf | Captain Katt | Mortimer Mouse | Ajax | Witch Hazel | El Capitan | Beagle Boys | Flintheart Glomgold | Magica De Spell | Millionara Vanderbucks | Beagle Babes | Grandpa Beagle | Julius | Frankenollie | Grace Goodwin

Disney Parks
Alien | Bartholomew Gore | Black Prince | Constance Hatchaway | Daisy de la Cruz | Hatbox Ghost | Hitchhiking Ghosts | Madame Leota | Master Gracey | Nebula Ghosts | Phantom | Pirates | S.I.R. | Werecat Lady | Yeti (Expedition Everest) | Yeti (Matterhorn Bobsleds)