With immense credit going to Disney's animated The Legend of Sleepy Hollow, the Headless Horseman was easily one of my favorite monsters as a child. This puts me in a bit of chicken-or-egg quandary though because I may have been drawn to the animated Headless Horseman through an obsession I've had with jack-o'-lanterns for as long as I can remember.
When I was a baby, my parents decorated my room with glowing jack-o'-lantern lamps including a scarecrow lamp with a grinning jack-o'-lantern face. Around the time I turned 2-years-old, my family moved to Florida and decided to give away these lamps prior to the move.
One of my earliest memories is watching (with bitter contempt) these lamps be given away to a family friend. Perhaps I was too young to have friends but I watched those grinning gourds leave like they were trusted and true comrades. Maybe I couldn't help but see the faces of those friends in the villainous grin of the Headless Horseman several years later.
It wasn't until recently that I realized I was remembering The Legend of Sleepy Hollow incorrectly and the pumpkin head was only used as a ruse by a local trying to scare Ichabod Crane. My disappointment was odd in its severity but I guess I felt somehow betrayed by my own memory. I didn't lose sleep over it or anything but to me, the Headless Horseman will always carry a jack-o-lantern head, despite how little that makes sense to the story.
I could say that my Headless Horseman smashes a seemingly endless supply of jagged-mawed gourds across his victims or holds the jack-o'-lantern head like a security blanket, traumatized by the loss of his own human head but I feel like the true answer defies explanation. It's an answer that only the ghosts can understand.
I was actually taken aback by how nefarious my rendition of the Headless Horseman turned out and, of the nine Classic Monsters illustrations, I consider this one to be the most disturbing. Perhaps it is colored by those bitter feelings I had as a 2-year-old, a dark emotional response clouding the innocent thoughts of a child.
The initial concept for my Headless Horseman illustration almost worried me with its lack of villainy. Upon looking up the traditional uniform of a Hessian artilleryman, I was actually excited by its lack of menace. I immediately thought of a cream-colored sky broken up by the limbs of dead trees. Against the blue jacket with red trim and that globular orange pumpkin, this would have no chance to be anything other than the most psychedelic and autumnal of my Classic Monsters series.
I think this shifted when, in a sort of trance, I sketched the Horseman's sword across the throat of his own horse. This not only alluded to the decapitation that made this spectre so notable but also showed his lack of allegiance. While I don't imagine that my Headless Horseman carries out the despicable deed of murdering his own horse, the insinuation disturbs me greatly, especially since the horse reacts with such complacence.
However, I feel that the horse itself is not a horse as you and I would know it. Rather, I think it is a droning entity from the phantom realms that resurrected the Headless Horseman, some sort of zombie steed with no soul in its abysmal eyes.
The Horseman's blade is rusted with a handle adorned with corroded metallic dead tree limbs and an equally corrupted metallic autumn leaf. Glimpses of the his dead skin visible between his black gloves and red cuffs exude a violet glow that also emanates from his neck and violently grinning jack-o'-lantern face.
I interpret this glow as his essence or possibly whatever passes as his soul. A pumpkin vine reaches into that essence creating some sort of brittle connection between head and body. While medals adorn his sash, they are unlike those of any army in our world. Instead, the cryptic symbols of crescent moon and dead leaf indicate some sort of merit in realms of the nocturnal and autumnal. But again, the sword crossing over the Horseman's own steed shatter any illusions of loyalty.
Anthropomorphic trees with hollow ghostly faces stretch from gray vapors to border the illustration. These loosely allude to McDonald's Happy Meal commercials from the '70s and '80s. I recall eating at McDonald's on Halloween sometime in the '80s in the Parkshore Shopping Center in Naples, Florida. This shopping center had a store that sold wicker furniture; it smelled like cinnamon and reminded me of witches. I imagine these trees smell like that store; cinnamon, wicker, and the smell of burning leaves.
The cannons flanking the horse are simply a reference to the cannons that took the Headless Horseman's head back when he was a Hessian artilleryman. The dynamic purposely recreates the Knight cards from tarot decks. A rainbow of autumn colors flanking the horse as well as the autumn colors worked into the canons aren't meant to indicate the Headless Horseman as a knight of the autumn. Rather, they're meant to create the fall atmosphere that incubates the Horseman's energy.
The peach skies and symbols create a tarot card-like collage invoking simpler times and the celebratory nature of the rustic harvest juxtaposed with the otherworldly horror of the Headless Horseman made clearer through the thinning boundary between our world and his.