The Legend of Sleepy Hollow

Greg Manchess

The Legend of Sleepy Hollow has captivated me since I was little. Just the words, “Sleepy Hollow,” bring images to mind. It’s the right amount of spooky with the right amount of Halloween tropes. Just scary enough.

I couldn’t read the story as a kid, even though I had an illustrated copy of Shirley Temple’s Storybook. Arthur Rackham’s pen and ink drawings inside were so devilish and weird that I couldn’t spend too much time looking at them for fear of nightmares. I later realized how brilliant they are.

Equally brilliant was Norman Rockwell’s painting of Ichabod Crane. Probably the best depiction of a character from literature out there. He painted it as an example to show publishers a set of posters he had in mind for libraries. Well known characters from popular stories. Such a great idea, but he never saw it realized. No one was interested.

Seriously? Norman Rockwell. Icabod Crane. Not interested.

This story has been on my list of Things To Paint for many years. At the top of the entries was the Headless Horseman. Then called last week and wanted something to illustrate the re-issue of the Washington Irving story in conjunction with the latest TV show.

The opportunity was perfect. My idea was a straight-up posed portrait and risked looking a little boring, but I knew the life of the piece would come out of the finished drawing. I’d painted and repainted it over and over in my head, so it was crystal clear. I sent Irene Gallo a quick thumbnail.

I’m already a fan of the show. Completely wacky and yet I’m drawn in every time I watch. So I didn’t want to show the horseman as a wild, horse-rearing, icon. Most artists depict that. I wanted mine to show potential, and let the viewer add the creepy, the drama, the Yikes Factor. Like a hollywood poster that teases the character.

This horseman sketch is slated for a large original oil painting, and perhaps a follow-up poster. Then it’s on to the Wicked Witch of the West, Flash Gordon, Ulysses, Scrooge, Robin Hood, etc, etc.