The Elder Scrolls V: Skyrim is definitely full of secrets and easter eggs that you won’t stumble upon even after completing multiple playthroughs. The Headless Horseman is one such secret that you can randomly encounter along the way.
YouTuber Steve Lee recently posted a video asking the Skyrim developers about their favorite creations in the game, and one developer shared how they managed to get the Headless Horseman to work without being immediately Treat NPCs as dead.
https://www.youtube.com/watch?v=Bo3eKUdociI/
In a nutshell, it goes like this: Because not having a head in Skyrim makes the game think you’re dead, the Headless Horseman has to endure having his head blown off repeatedly every time he encounters him.
When he spawns, his head is destroyed, which happens out of the player’s line of sight, so you never see the Horseman lose his head. Still, it’s an interesting and rather disturbing detail to know that the ghost that wanders the paths of Skyrim becomes headless only moments before you meet him.