“To the Headless Horseman” finds a rider who acts as a manifestation of something that never goes away.

Track: “To the Headless Horseman”
Album: Dark in Here (2021)

It feels a little abstract and your takeaway may be different than mine, but “To the Headless Horseman” seems to be a song about the sliding doors effect of who you could have been. The narrator imagines a stranger passing them on the road constantly and thanks God for bounty hunters who don’t take their marks down. We hear that this person fears being caught in a sense and that they feel like they’re just evading the proverbial hangman over and over. Sure, there’s space for some literal reading there with the title, but the obvious jump is to what put you in that headspace in the first place.

You imagine yourself living day-to-day because of the grace of some other force, but that thing visiting you could be part of your past. It fits with many other Mountain Goats songs to imagine a person haunted by their choices and their past self, pictured here as a spectral force. The struggle is not just with the memory but with the ways that memory manifests. It’s not a literal ghost, but in a sense it is the ghost of who you were when those things happened. This is a song that has enough room for very diverse readings, but I feel that specific shudder in this narrator.