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Sleepy Hollow - Headless Horseman

"Such is the general purport of this legendary superstition, which has furnished materials for many a wild story in that region of shadows; and the spectre is known at all the country firesides, by the name of the Headless Horseman of Sleepy Hollow." - Washington Irving

I started off the challenge of designing the Headless Horseman with great enthusiasm. I started off very experimental, using inks, watercolor, permanent marker, paper towels and paper cutouts. I honestly didn't know where to start, so I just jumped in head first. I focused on what Ichabod Crane would be scared of - spiders, ghosts, ghoulish soldiers, zombies, skeletons, etc.

 

 I drew this piece while waiting for my laundry to dry at Washingtown. I really liked the idea of the jack-o-lantern being his face and being able to show his emotion. It was kinda crazy and had a lot of gag potential. But...it was kind of obvious. It's been done before.

Also, the overall shape was pretty similar to my vision for Ichabod. Tall, spider-like limbs. When put together, there's no contrast...back to the drawing board.
 "Another of his sources of fearful pleasure was to pass long winter evenings with the old Dutch wives, as they sat spinning by the fire, with a row of apples roasting and spluttering along the hearth, and listen to their marvellous tales of ghosts and goblins, and haunted fields, and haunted brooks, and haunted bridges, and haunted houses, and particularly of the headless horseman, or Galloping Hessian of the Hollow, as they sometimes called him."  - Washington Irving


So I went back to the ghoulish soldier idea - the galloping Hessian soldier. I started drawing him rounder, more barrel-chested. I liked that. that is a shape I could contrast against the tall, thin Ichabod.


But my Headless horseman still didn't have a personality. Ichabod would be scared of him, yes, but who was he?
 Then I started exploring what he was like when he was alive, before/during the American Revolutionary War. I landed on this design and saw some potential for a boisterous, short, round, Danny Devito type character.
 I gave him 2 flaws - an affinity for booze & bar maids.

Part of the Headless Horseman's character is his horse. You can't forget the horse!
His horse is his best friend.
 In the end, I decided my Headless Horseman still had a head...well, a detachable head. His head would be like a hair piece. Everyone knows it's all an act.


 Headless Horseman and Horse shenangigans.


Part of my Headless Horse Character Model Packet - expression chart and turn arounds before/after he was headless.

I'd recommend the Advanced Character Design Workshop at Animation Collaborative with Chris Sasaki to anyone who wants to get better at designing well rounded characters. 

*It's important to say that you get out what you put into it...and boy, did I put in some pencil mileage!

A big thanks to Chris for all the help, encouragement & draw overs! 

Check out a few of my classmates' work:






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