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Countdown: 9 Songs to Keep Halloween Weird

Written by on October 23, 2026

Once again, we have entered the season of macabre delights, in which we find ourselves surrounded by plastic cadavers, hollowed-out squash, and whatever in God’s name the Scarionette is supposed to be. (If you are unfamiliar with what I speak of, please do yourself a favor and remain that way.) Ever since laying my eyes upon a life-sized rubber skull in Mapes Toy Store at the age of three, I have loved all things spooky, and I’m forever glad to watch them emerge en masse from the shadows to congregate in our neighborhoods every October. In the words of Bob Dylan, “The clouds are turnin’ crimson / The leaves fall from the limbs an’ / The branches cast their shadows over stone.” Or, as I Think You Should Leave comedian and noted Halloween enthusiast Tim Robinson says of the holiday: “some of my favorite times of year, the scariest—the scary seasons that are… the seasons where the smells change.”

To accompany these changing sights and smells, I am pleased to present some of my personal favorite sounds of Halloween. Rather than devote more attention to established favorites, however, I hope to highlight some spooky masterpieces that have received relatively less appreciation, or, at least, are less popularly associated with Halloween (and less likely to be heard in a Reese’s ad). As a result, we will not be discussing “Thriller,” “Spooky Scary Skeletons,” or “The Monster Mash,” wonderful though they may be. We won’t even be dipping into the treasure trove of morbid rock and metal classics like “(Don’t Fear) The Reaper,” “Riders on the Storm,” “Black Sabbath,” “Raining Blood,” “Zombie Attack,” and so on, though metal has produced arguably more Halloween-themed bands, songs, and album covers than any other genre.

Instead, we’ll focus on the stranger side of things, hearing from the likes of Tom Waits, Miles Davis, Frank Zappa, the Sonics, and even Captain Beefheart & His Magic Band (among others). This was originally intended to be a one-off article, but since I’ve found myself having a lot to say—and falling way behind on my suggested posting schedule in the process—I have decided to expand it into a Halloween Advent calendar of sorts. Every day for the next week (and two days), I will review one spooky song, culminating in the spookiest of them all on October 31st… Enjoy!

  1. “Million Miles”—Bob Dylan, Time Out of Mind, 1997

Starting us off is the poet king himself, “His Bobness” (to quote Tom Petty). Dylan’s voyages have brought him into frightful territory on a number of tunes, none more blatant than 2020’s “My Own Version of You.” Here, he spends months “visiting morgues and monasteries / Looking for the necessary body parts / Limbs and livers and brains and hearts” in a quest to create—as other listeners have noted—his own Frankenstein’s monster. “Million Miles” is, admittedly, farther removed from the literal undead, instead detailing a breakup that has left our singer in a state of emotional purgatory. However, some of the images Dylan uses to evoke this waking nightmare strongly suggest the supernatural; for instance, he complains of “voices in the night trying to be heard,” lamenting, “Maybe in the next life I’ll be able to hear myself think.”

What’s more, the track is the closest musical equivalent to a night spent lost in the woods that I’ve ever heard. The making of Time Out of Mind was famously disjointed; as Dylan himself would later say, “that album sounds to me a little off. There’s a sense of some wheels going this way some wheels going that, but hey, we’re just about getting there.” Combine this “off”-ness with producer Daniel Lanois’s penchant for hazy aura, and you’ve perfectly described the vibe of “Million Miles.” Creaking rhythm guitars play slightly out of time with the slow swing of the ride cymbal, a haunted-house organ hopping over the sinking bass all the while. The whole band creeps along like a rickety jalopy, pushing and pulling, one lumbering organism that seems to hold itself together through sheer will. Of particular interest are the snare rolls and cymbal crashes supplied by either jazz legend Brian Blade or rock icon Jim Keltner—both drummers are credited on the track—as well as the sporadic, bluesy cloudbursts of former Fabulous Thunderbirds guitarist Duke Robillard, all of which help keep the track from becoming lifeless (pardon the pun). And thanks to Lanois’s spacious recording, the whole affair sounds as if it’s taking place somewhere in the wilderness, echoing the distance evoked by the title. (For an equally moody but cleaner, more conventional recording, check out Bonnie Raitt’s 2012 cover from the album Slipstream. As always, her slide-guitar playing is top-notch.)

And thus, we have rolled to the end of our inaugural paranormal review. Until tomorrow…

Sources:

https://www.bobdylan.com/songs/moonlight/

https://www.womansday.com/life/g62333884/vintage-halloween-photos/

https://www.bobdylan.com/songs/million-miles/

https://www.bobdylan.com/songs/my-own-version-of-you/

https://pitchfork.com/reviews/albums/bob-dylan-rough-and-rowdy-ways/

https://en.wikipedia.org/wiki/My_Own_Version_of_You

https://en.wikipedia.org/wiki/Time_Out_of_Mind_(Bob_Dylan_album)#Personnel

https://en.wikipedia.org/wiki/Duke_Robillard