Heaven's Gate

The True Story of the Headless Horseman & Sleepy Hollow ( w/ J.W. Ocker 🎃 )

Somewhere in the SkiesOct 26, 2026

Author J.W. Ocker joins Ryan Sprague to explore the real history behind Washington Irving's 'The Legend of Sleepy Hollow' and his book 'Chasing the Headless Horseman.' Ocker argues the original story contains no supernatural elements and that Brom Bones was the Horseman, but he also traces the legend to a real Hessian soldier decapitated by a cannonball, possibly named Heinrich Range. The conversation also covers Irving's surprising role in shaping modern Christmas, the tourism tensions in Sleepy Hollow and Tarrytown, and how a failed 1950s UFO cult prophecy gave the world the term 'cognitive dissonance.'