The Headless Horseman - Audio Biography

Biography Flash: Headless Horseman Outrides Taylor Swift in Epic September Showdown


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The Headless Horseman Biography Flash a weekly Biography.

If you asked me “Who had a bigger week in September: Taylor Swift or the Headless Horseman?” — I’d say, funny enough, only one of them rode into two parades on horseback stealing the show and, I assume, not writing lyrics about their exes. Yes, folks, your favorite legendary neckless equestrian is galloping through headlines and more Halloween events than my inbox gets crypto spam right now.

First off, if you were anywhere near Disney’s Magic Kingdom on September 3 — the Boo to You Parade kicked off its Halloween season with our guy leading the spooky charge, and he looked about as unfazed by the spectacle as a podcaster in his seventh hour of editing. If you blinked, you missed it, but don’t worry — the internet lit up with #headlesshorseman, #bootoyou, and a couple of “how is he reading the parade map?” jokes. Disney’s California Adventure is also going all in, with the Headless Horseman riding ahead of their Frightfully Fun Parade. I counted at least three toddlers fleeing on video, adding a solid 74% to my recommended daily dose of schadenfreude.

If you’re in New York, it’s all about the NYC Halloween Parade prepping for October 31. Organizers are already hyping “the legend that inspired Halloween’s greatest costume,” and I swear every year I see last-minute attempts to merge Horseman chic with Catwoman tights — bold, but still less terrifying than a subway rat. Sixth Avenue will host tens of thousands of costumed humans, one costumed horse, and at least sixteen social media influencers threatening to “go viral” as the Horseman. “The Headless Horseman’s Hideaway” is also being built at Van Cortlandt Manor for the Great Jack O’Lantern Blaze, which should give our hero a pumpkin spa retreat to rest his — head?

Speaking of pumpkins, Sleepy Hollow itself is busy. This weekend there’s a “Paint a Headless Horseman Pumpkin” event. I’m hoping someone does a self-portrait, because nothing says meta like a decapitated pumpkin painting itself. Some immersive magic shows are promising to “summon the Horseman’s spirit,” though I’m skeptical about spirits who spend most of their evenings at hayrides and puppet shows. The Frogtown Mountain Puppeteers are rerunning their comedic “find a spookier image for the Horseman” extravaganza, which sounds suspiciously like every influencer’s Instagram brainstorming session.

Pure speculation, but with this level of sustained hype, I’m predicting the Horseman will out-trend most actual political candidates by midpoint October. If you spot him on a TikTok livestream, let the myth live on — just warn him to steer clear of Taylor Swift fans.

That’s the latest on the Headless Horseman: parody, pageantry, pumpkin art, and a parade of pure Halloween glory. Subscribe so you never miss a “Biography Flash” and search the term “Biography Flash” for more quirky deep-dives from me, Marcus Ellery. Thanks for listening, and as always, beware of guys on horses after dark.

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The Headless Horseman - Audio BiographyBy Inception Point Ai