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Headless: A Sleepy Hollow Story (Web Video)

 Headless: A Sleepy Hollow Story (Web Video)
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TVTItem
 Headless: A Sleepy Hollow Story (Web Video)
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Headless: A Sleepy Hollow Story (Web Video)
 Headless: A Sleepy Hollow Story (Web Video)
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HeadlessASleepyHollowStory
 Headless: A Sleepy Hollow Story (Web Video)
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Headless: A Sleepy Hollow Story, also known as Headless Series, is a 2022 modern web series adaptation of the Washington Irving short story "The Legend of Sleepy Hollow", by Shipwrecked Comedy. It follows Ichabod Crane, a science teacher from Hartford, who just moved into the odd town of Sleepy Hollow, NY. After moving in, he realizes he must become roommates with the Headless Horseman. The two embark to discover the true head of the horseman throughout the 10-episode series. In each episode, the horseman takes on a new head and personality, and the two meet residents of the town who might be able to help.The series also included the companion series, Unsolved Babesteries, following Brom's Babes as they explore the mysteries of Sleepy Hollow in a BuzzFeed Unsolved-style Show Within a Show.Headless premiered on Shipwrecked's Youtube channel on August 29, 2022, while Unsolved Babesteries premiered on the same channel on September 15, 2022.
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White Anglo-Saxon Protestant
 Headless: A Sleepy Hollow Story (Web Video) / int_11cdc5d8
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White Anglo-Saxon Protestant Ichabod Crane is played by Indian-American Sean Persaud.
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Arc Symbol
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Arc Symbol: The symbol on Ichabod's Orphan's Plot Trinket necklace is the same as the one on the Horseman's sword. Part of Ichabod's reasoning for helping the Horseman find his head is to get answers for what the symbol means.
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Urban Legends
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comment
Urban Legends: Sleepy Hollow is full of them: The Headless Horseman is of course the biggest one, a Hessian mercenary beheaded during the Revolutionary War who roams the woods still looking for his head. While the Horseman is revealed to be real, Episode 4 reveals he may not be a Hessian mercenary after all, since the nearest Revolutionary battle took place ten miles away. Anneke Storms founded the Storms Inn as a girls' orphanage, but disappeared a year later. Anneke is rumored to have been a witch. The Woman in White is said to haunt the woods, warning others to stay away from Raven Rock so they aren't caught and killed in a storm, as she was.
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Arbitrary Skepticism
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Arbitrary Skepticism: Kat expresses skepticism about the existence of the Headless Horseman, despite the fact that her best friend is a bonafide witch. This might be more because Brom was the one telling the story than the story itself, considering how easily she accepts the Horseman in Episode 4. Ichabod, likewise, says he doesn't fully believe in the supernatural despite witnessing Matilda's magic firsthand just moments before (though this might have been to impress Kat).
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Relatively Flimsy Excuse
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comment
Relatively Flimsy Excuse: In Episode 3, Ichabod covers for Gravy's unexplained appearance by calling him his cousin. When he later calls him his uncle, Kat gets confused. In Episode 4, he tells her Max is another cousin, and in Episode 6, he gives the same excuse to Baltus when Anne appears as "Mahk" unexpectedly.
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The Tease
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comment
Katrina in the original story is a wealthy heiress and an implied tease, using Ichabod to make Brom jealous. Here, Kat is a Troubled, but Cute Little Miss Snarker who doesn't pay much mind to Brom or her father's status, wishing to get out of Sleepy Hollow.
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Childhood Friends
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Childhood Friends: Kat and Matilda have been friends a long time, with each carrying a photo of them at the beach with Kat's mom when they were little girls. This is why Matilda was willing to sacrifice Rip Van Winkle so Kat would come back. Brom, the Babes, and Spike are also implied to be this, since they've all known each other since at least high school.
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Adaptational Villainy
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Adaptational Villainy: Kat and Baltus. While Katrina Van Tassel could be accused of leading Ichabod on, depending on one's interpretation, Kat full out is willing to kill multiple people in order to stay alive. Baltus, meanwhile, kickstarted the whole issue by lying to Kat and attempting to poison Rip.
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Black Comedy
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Black Comedy: A couple of the heads make very light of their deaths, and Matilda and Verla both tend to say some disturbing things in a Crosses the Line Twice sort of way.
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Caper Crew
 Headless: A Sleepy Hollow Story (Web Video) / int_226875bb
comment
In Episode 8, the entire Caper Crew barely manage to disguise their faces while trying to break into Storms' Inn: Ichabod, Brom, and even Kat wear fake mustaches when talking to Lucretia (who is familiar with all of them) and Douffe wears a maid outfit, without changing her face. Parodied — Lucretia/Oksana sees right through the disguises and manages to capture most of the crew — the only ones she didn't catch were the ones she never actually encountered.
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Nepotism
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Nepotism: Implied, since pretty much every mayor mentioned in the series since the town's founding has been a Van Tassel.
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Chekhov's Gun
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comment
Gravy Davy Crowbones seems like just one of the many guest-star heads, but his treasure chest ends up holding the literal and figurative keys to the mystery of the Horseman. (See Chekhov's Gun above).
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Adaptation Expansion
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comment
Adaptation Expansion: The short story's plot is essentially covered in the first episode (new teacher in town goes to a party and gets spooked by the Headless Horseman), while the rest follows Ichabod's attempts to find the Horseman's head.
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Adaptational Job Change
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Adaptational Job Change: A very slight one for Ichabod: In the original story, he is the schoolmaster, meaning he taught all subjects in a one-room classroom. Here, he is the science teacher, so he only teaches one subject. In the original story, Brom is a local strongman, while here he is the Phys Ed teacher. Baltus Von Tassel was originally simply a wealthy farmer, while here he is the mayor.
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Related in the Adaptation
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Related in the Adaptation: Douffe Martling and Geoffrey Crayon are a married couple (though both were apparently catfished into it). They later get divorced.
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Companion Show
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Companion Show: Serves as one to Headless, showing the Babes' perspective of certain events and providing some clues to the overall mystery.
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Mythology Gag
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comment
Mythology Gag: Geoffrey Crayon was the name of the pseudonymous narrator of Irving's essay and short story collection, The Sketch Book of Geoffrey Crayon, Gent, in which "The Legend of Sleepy Hollow" and "Rip Van Winkle" first appeared. Crayon, however, does not claim to have written either tale, but overheard them (which might be why Diedrich is the bard, not Crayon). Crayon was also characterized as a snarky character who at once scoffed at the supernatural and got caught up in it, making it appropriate that he's a doctor who helps cover up a supernatural resurrection. One of Kat's outfits includes black and white stripes as a reference to one of Katarina Von Tassel's iconic dresses from the award-nominated Sleepy Hollow (1999). In Episode 1, Brom pretends to be the Headless Horseman to scare Ichabod in the woods, just as he did in the short story. Unlike the story, Ichabod recognizes Brom from his Sperrys, and the real Headless Horseman shows up just afterwards. Rip Van Winkle has once again disappeared in the Appalachian woods... just not under the same circumstances. In addition, the spell he's under puts him in a deep sleep (although he only misses a year instead of 20). In Episode 2, Ichabod uses a pumpkin for the Horseman's head before going to see Matilda. Many depictions of the Headless Horseman give him a Jack O' Lantern head. Elizabeth Van Tassel wrote a book called Legends of Sleepy Hollow, referencing the real life title of the short story the series is based on. Jonathan Oldstyle was Washington Irving's first pseudonym, from before he wrote short stories. A character named after him appears as a rival bard to Diedrich. In the finale, Ichabod gets a bicycle he has named "Gunpowder", the name of the horse Ichabod rode home in the original short story.
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Alliterative Title
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comment
Alliterative Title: Each episode has one of these, such as "Ghosts in the Graveyard" and "The Briny Booty". See Idiosyncratic Episode Naming.
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Funny Background Event
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comment
Funny Background Event: Diedrich falls asleep in the back row during the play in Episode 4. Ichabod becomes increasingly put-out by Paulie's elaborate plan in Episode 8.
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Everyone Went to School Together
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comment
Everyone Went to School Together: Justified since it's a small town, but Kat, Matilda, and Brom were all in the same year in high school. Brom's Babes and Spike were presumably there around the same time. Averted with Ichabod, who grew up outside of Sleepy Hollow.
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Witness Protection
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Witness Protection: Lucretia turns out to be in this, as she is actually international super spy Oksana Bolshekov.
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Auto-Tune
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In Episode 5, the typical end credit song switches to Devlyn's in-universe Auto-Tune song, "When Did You Have Time (To Make All this Slime?)", and shows more of her video.
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Don't Go in the Woods
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Don't Go in the Woods: Brom warns Ichabod not to go into the woods at night (and for good reason considering Rip Van Winkle, the previous science teacher, was last seen in those same woods.) The local legend of the Woman in White supposedly warns travelers to stay away from Raven Rock so they aren't caught and killed in a storm, as she was. Max Lee and Spike were shaken up by their encounters with her years before.
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Weird Trade Union
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Weird Trade Union: Diedrich is part of the Bards' Union, which requires a four-hour break every 30 minutes.
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Conspiracy Theorist
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comment
There is evidence the Half Moon was not the only ship on that voyage that made it to America (which is made up for Headless). Confirmed by Kat and Matilda's photo, which shows them and Elizabeth Van Tassel with the remnants of the Liechtgevund, Henrietta's ship. Elizabeth also questioned the "Henry Hudson as founder" story before her death, but was dismissed as a Conspiracy Theorist.
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FoundFootage
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comment
Found Footage: Downplayed. The series is framed as a show filmed at the Sleepy Hollow Public Access station that was immediately archived for nonsense and not shown to the public "...until now".
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Flat Character
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comment
Katrina Van Tassel is mostly a Flat Character who never left Sleepy Hollow and is implied to have her family in tact, but Kat briefly went away to college before dropping out and returning home to do odd jobs, and lost her mom when she was 10. She is later revealed to have been accidentally poisoned a year prior to the series, and got close to Ichabod only to use his life force to extend hers.
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Unrelated in the Adaptation
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comment
Unrelated in the Adaptation: Rip Van Winkle and Judy Gardenier (Judith Van Winkle-Gardenier in the original short story) show no indications of being related in this series.
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Fainting
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comment
Fainting: Gravy does this after he's gotten too drunk. Ichabod Faints in Shock after Gravy stabs Douffe. Judy also Faints in Shock when she sees Headless for the first time, despite being told about it in advance.
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Stylistic Suck
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Stylistic Suck: The opening credits have a very homemade quality, and there are multiple sections shot from a camera phone.
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Left It In
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comment
Left It In: Justified and lampshaded. Eugene at one point says he will cut one of Tripp's terrible puns, but Tripp says, "No you won't. You're going to like that later."
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Killed Offscreen
 Headless: A Sleepy Hollow Story (Web Video) / int_423f5a19
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Diedrich sticks around Sleepy Hollow as a ghost after getting Killed Offscreen and killed again as Headless.
 Headless: A Sleepy Hollow Story (Web Video) / int_423f5a19
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Our Witches Are Different
 Headless: A Sleepy Hollow Story (Web Video) / int_439a64d3
comment
Our Witches Are Different: Witches here have inherent abilities, which are assisted by herbs, stones, and spells. They are able to imbue objects with magic as well. Matilda is a practicing witch able to briefly bring the dead back to life via the Headless Horseman, and a witch's coven existed in Sleepy Hollow as far back as its founding.
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Southies
 Headless: A Sleepy Hollow Story (Web Video) / int_43d37acf
comment
Anne Tarry's "Mahk" disguise is basically her in a fake mustache, baseball cap, and thick Southies accent. It somehow manages to fool her former boss.
 Headless: A Sleepy Hollow Story (Web Video) / int_43d37acf
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In-Universe
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In-Universe, Max Lee corrects the Trousers' play, claiming: There is evidence the Half Moon was not the only ship on that voyage that made it to America (which is made up for Headless). Confirmed by Kat and Matilda's photo, which shows them and Elizabeth Van Tassel with the remnants of the Liechtgevund, Henrietta's ship. Elizabeth also questioned the "Henry Hudson as founder" story before her death, but was dismissed as a Conspiracy Theorist. The nearest Revolutionary War battle was not in Sleepy Hollow, but in White Plains, 10 miles away (which is Truth in Television). This clues Matilda and Ichabod in to the fact that Headless isn't a Hessian mercenary after all.
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Historical Character's Fictional Relative
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Historical Character's Fictional Relative: Explorer Henry Hudson is given a wife named Henrietta Hudson, who captained one of the ships in the same fleet and was the leader of a witch coven, before getting turned into the Headless Horseman. The real Henry Hudson's wife was named Katherine, and she stayed behind in the Netherlands.
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Bad Influencer
 Headless: A Sleepy Hollow Story (Web Video) / int_4802c03d
comment
Devlyn Versace, Bad Influencer prankster died not once, but twice — first, in the middle of a prank while bungee jumping out of a blimp, and second via head-melting after humiliating Ichabod and leaving him unable to defend himself in court.
 Headless: A Sleepy Hollow Story (Web Video) / int_4802c03d
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Paper-Thin Disguise
 Headless: A Sleepy Hollow Story (Web Video) / int_48b9731f
comment
Paper-Thin Disguise: In Episode 1, Brom's Headless Horseman disguise is given away by his cheap mask and Sperrys. Literally — In Episode 4, the Horseman comes in holding a mask in front of his nonexistent head as a disguise. Anne Tarry's "Mahk" disguise is basically her in a fake mustache, baseball cap, and thick Southies accent. It somehow manages to fool her former boss. In Episode 8, the entire Caper Crew barely manage to disguise their faces while trying to break into Storms' Inn: Ichabod, Brom, and even Kat wear fake mustaches when talking to Lucretia (who is familiar with all of them) and Douffe wears a maid outfit, without changing her face. Parodied — Lucretia/Oksana sees right through the disguises and manages to capture most of the crew — the only ones she didn't catch were the ones she never actually encountered.
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type
Leaning on the Fourth Wall
 Headless: A Sleepy Hollow Story (Web Video) / int_4a3e547f
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Leaning on the Fourth Wall: Certain comments, particularly by Ichabod, lean this way: "How can I understand you?" (about the Horseman's hand gestures) "This guy looks 30." (about supposedly 14-year-old Trevor) "When did you have time to make all this slime?!" (about Devlyn somehow finding the time to make slime to pour on Ichabod between coming back to life and going into court. Backed up by a caption in her video where she wonders, "When DID I have time to make all this slime?"
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Wham Line
 Headless: A Sleepy Hollow Story (Web Video) / int_4e7c4536
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Wham Line: "Wait... Spike saw the [Woman in White] after Kat's mom went missing."
 Headless: A Sleepy Hollow Story (Web Video) / int_4e7c4536
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Wham Shot
 Headless: A Sleepy Hollow Story (Web Video) / int_4e7f703c
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Wham Shot: In Episode 1, the closeup on the Horseman's sword, bearing the same symbol as Ichabod's necklace, is this. In Episode 3, Captain Crowbones stabs Douffe in the abdomen, leaving Ichabod to faint deadaway. Cut to credits.
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Animated Credits Opening
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Animated Credits Opening: Starting in Episode 2, the opening credits are animated.
 Headless: A Sleepy Hollow Story (Web Video) / int_4eddbc06
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We Used to Be Friends
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We Used to Be Friends: Much of the B-plot centers around the split between the Babes and Spike, the former fourth Babe, as they try to make amends.
 Headless: A Sleepy Hollow Story (Web Video) / int_51a3ba7
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 Headless: A Sleepy Hollow Story (Web Video) / int_56515a39
type
Artistic License – History
 Headless: A Sleepy Hollow Story (Web Video) / int_56515a39
comment
Artistic License – History: Both In-Universe and in reality with the Show Within a Show, A Brief History of Sleepy Hollow. Henrietta Hudson as a legitimate ship captain ignores the fact that women were not legally allowed to take seafaring professions until the 20th century (though there are records of female pirate captains, which was illegal whether you were female or not). Henry Hudson really did sail from Amsterdam on the Half Moon and land in what would become the Hudson Valley, where Dutch settlements like Sleepy Hollow were born, and really did disappear soon after a mutiny while traveling north. But his wife's name was Katherine rather than Henrietta, she never captained a ship, and there were no other ships on the voyage with Henry in general. He also neither founded nor named anyone the mayor of Sleepy Hollow. It later turns out that "Henry Hudson as founder" is an Ancient Conspiracy in the Headless universe, with the real founder being Henrietta Hudson. This became a Suppressed History when she was cursed to become the Headless Horseman. In-Universe, Max Lee corrects the Trousers' play, claiming: There is evidence the Half Moon was not the only ship on that voyage that made it to America (which is made up for Headless). Confirmed by Kat and Matilda's photo, which shows them and Elizabeth Van Tassel with the remnants of the Liechtgevund, Henrietta's ship. Elizabeth also questioned the "Henry Hudson as founder" story before her death, but was dismissed as a Conspiracy Theorist. The nearest Revolutionary War battle was not in Sleepy Hollow, but in White Plains, 10 miles away (which is Truth in Television). This clues Matilda and Ichabod in to the fact that Headless isn't a Hessian mercenary after all.
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Creative Closing Credits
 Headless: A Sleepy Hollow Story (Web Video) / int_5f91efd9
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Creative Closing Credits: In Episode 5, the typical end credit song switches to Devlyn's in-universe Auto-Tune song, "When Did You Have Time (To Make All this Slime?)", and shows more of her video. In Episode 7, the end credit song switches to a more jazzy Ocean's Eleven-esque tune, due to the appearance of Paulie Tahoe and the plan to break into Storms Inn next episode.
 Headless: A Sleepy Hollow Story (Web Video) / int_5f91efd9
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Freeze-Frame Bonus
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comment
Freeze-Frame Bonus: The walls of Colonial Drugs 'n' Stuff are full of surreal posters and pictures. In Episode 5, the Recommended Videos and search box text for Devlyn's Youtube page include such tidbits as: Various videos on fanny pack uses. "Why Guy Ferrari and I are calling it quits" "Damn, Convinced My Little Sis She's Dead" "American Whoopee 95th Anniversary Criterion..." "devlyn versace streamy award meltdown"
 Headless: A Sleepy Hollow Story (Web Video) / int_62f9d08e
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Rich Bitch
 Headless: A Sleepy Hollow Story (Web Video) / int_644eca71
comment
Douffe gets stabbed in Episode 3, having been a generally unpleasant Rich Bitch who constantly raised Ichabod's rent for unfair reasons and tried to take something that wasn't hers as collateral. Helps that she's Only Mostly Dead.
 Headless: A Sleepy Hollow Story (Web Video) / int_644eca71
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 Headless: A Sleepy Hollow Story (Web Video) / int_66dfe36a
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Missing Mom
 Headless: A Sleepy Hollow Story (Web Video) / int_66dfe36a
comment
Max Lee describes the Woman in White as a blonde woman. Between her blonde hair and wearing a lot of white, Kat was suspected to be connected to the Woman in White, if not the Woman herself. However, Spike later reveals he saw her as a redheaded woman, heavily implying that the Woman in White at some point became Kat's Missing Mom.
 Headless: A Sleepy Hollow Story (Web Video) / int_66dfe36a
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 Headless: A Sleepy Hollow Story (Web Video) / int_680f950
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Gilligan Cut
 Headless: A Sleepy Hollow Story (Web Video) / int_680f950
comment
Gilligan Cut: In Episode 2: In Episode 7, Brom says Lucretia will let him investigate Storms Inn since they're super close. Cut to Lucretia, hosting a wedding at the inn, threatening to carve Brom's eyeballs out if he or his friends are seen anywhere near the inn for the wedding.
 Headless: A Sleepy Hollow Story (Web Video) / int_680f950
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The Reveal
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The Reveal: The passed-down curse referred to in Elizabeth Van Tassel's manuscript has nothing to do with the Headless Horseman, but the Woman in White. And the Woman Spike saw back in high school looked different from the one Max Lee saw in 2004. The Woman in White changed appearance after Kat's mom disappeared, implying the curse passed on to her.
 Headless: A Sleepy Hollow Story (Web Video) / int_6b2b3b59
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Meaningful Name
 Headless: A Sleepy Hollow Story (Web Video) / int_6bda9a30
comment
Meaningful Name: Conversed in Episode 1, and brought up later in the series. Ichabod means "absent glory". Ichabod Crane comments that while it's insulting, he sees this meaning as an opportunity. This is fulfilled when Ichabod restores his family's honor and receives Henrietta's sword, "Glory". Ichabod says Katrina means "unsullied and pure". By the time Ichabod meets her, however, this has been inverted, as she is only alive because she's feeding off of another's life.
 Headless: A Sleepy Hollow Story (Web Video) / int_6bda9a30
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Grave Robbing
 Headless: A Sleepy Hollow Story (Web Video) / int_720e0c25
comment
Grave Robbing: Getting heads to use for Matilda's spell requires this, though the skulls of "Henri" and Gravy Davy Crowbones were already on hand.
 Headless: A Sleepy Hollow Story (Web Video) / int_720e0c25
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 Headless: A Sleepy Hollow Story (Web Video) / int_77414bc2
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Action Prologue
 Headless: A Sleepy Hollow Story (Web Video) / int_77414bc2
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Action Prologue: Episode 1 opens a year prior to the series proper, where Rip Van Winkle gets chased down by a mysterious figure in the woods.
 Headless: A Sleepy Hollow Story (Web Video) / int_77414bc2
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 Headless: A Sleepy Hollow Story (Web Video) / int_7a3dd888
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Real Men Wear Pink
 Headless: A Sleepy Hollow Story (Web Video) / int_7a3dd888
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Real Men Wear Pink: Brom, the Babes, and Eugene Trousers all show up in pink clothes at least once throughout the series. The Horseman also carries a pink parasol when out in town without a head.
 Headless: A Sleepy Hollow Story (Web Video) / int_7a3dd888
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 Headless: A Sleepy Hollow Story (Web Video) / int_7fd142ef
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Shared Universe
 Headless: A Sleepy Hollow Story (Web Video) / int_7fd142ef
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Shared Universe: With some of Shipwrecked's past projects: "American Whoopee 95th Anniversary Criterion..." is featured as a Youtube thumbnail, indicating a full 1925 film based on the skit actually exists in the Headless universe. Devlyn prank calls someone named Monica about winning a lifetime supply of Activia, which may have been one (or both) of the Monicas from The Bookfarters Saga.
 Headless: A Sleepy Hollow Story (Web Video) / int_7fd142ef
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Betrayal Insurance
 Headless: A Sleepy Hollow Story (Web Video) / int_803e411
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Betrayal Insurance: Baphomet's Eyelashes will melt the head right off of the Horseman if the identity he takes on gets too out of control.
 Headless: A Sleepy Hollow Story (Web Video) / int_803e411
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 Headless: A Sleepy Hollow Story (Web Video) / int_80a247a9
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Breather Episode
 Headless: A Sleepy Hollow Story (Web Video) / int_80a247a9
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Breather Episode: "The Chaos in the Court" is lampshaded as this in Unsolved Babesteries. Doubles as foreshadowing, since the next episode, "The Distractions at Dinner", was indeed a plot-heavy episode.
 Headless: A Sleepy Hollow Story (Web Video) / int_80a247a9
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 Headless: A Sleepy Hollow Story (Web Video) / int_82a64c4b
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Adaptational Nice Guy
 Headless: A Sleepy Hollow Story (Web Video) / int_82a64c4b
comment
Adaptational Nice Guy: The Headless Horseman is usually the antagonist trying to scare/murder Ichabod in Sleepy Hollow media. Here, they are just roommates who must work together to find the horseman's head. Brom Bones is more friendly towards Ichabod in this version, though there are still touches of jealousy on Brom's part. He's also against misogyny and hazing, so his possessiveness of Kat and his pranks on Ichabod are greatly toned down. Ichabod, to a lesser extent — the original character turned into a selfish gold digger due to the prospect of marrying Katrina by the climax, while in Headless he genuinely falls for Kat before knowing she's the mayor's daughter and remains sweet and humble throughout.
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Public Domain Canon Welding
 Headless: A Sleepy Hollow Story (Web Video) / int_85f620bf
comment
Public Domain Canon Welding: While the series is mainly based on "The Legend of Sleepy Hollow", modern versions of multiple Washington Irving characters show up in some way, shape, or form.
 Headless: A Sleepy Hollow Story (Web Video) / int_85f620bf
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 Headless: A Sleepy Hollow Story (Web Video) / int_875615dd
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Truth in Television
 Headless: A Sleepy Hollow Story (Web Video) / int_875615dd
comment
The nearest Revolutionary War battle was not in Sleepy Hollow, but in White Plains, 10 miles away (which is Truth in Television). This clues Matilda and Ichabod in to the fact that Headless isn't a Hessian mercenary after all.
 Headless: A Sleepy Hollow Story (Web Video) / int_875615dd
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 Headless: A Sleepy Hollow Story (Web Video) / int_8967e17f
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Back from the Dead
 Headless: A Sleepy Hollow Story (Web Video) / int_8967e17f
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Back from the Dead: Matilda's spell combines the life force of the Horseman's body with the spirit from whatever skull they they choose to place on his neck. The Horseman then takes on the identity of the skull, briefly bringing that person back to life (complete with clothes they would have worn). However, no one head can last for very long, so they keep having to switch out heads. Kat turns out to be this, since she died a year before the series started. Diedrich sticks around Sleepy Hollow as a ghost after getting Killed Offscreen and killed again as Headless.
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Denser and Wackier
 Headless: A Sleepy Hollow Story (Web Video) / int_8a07e085
comment
Denser and Wackier: Headless may be quirky, but Unsolved Babesteries is a whole other level of silly.
 Headless: A Sleepy Hollow Story (Web Video) / int_8a07e085
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 Headless: A Sleepy Hollow Story (Web Video) / int_8e5c862
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Ancient Conspiracy
 Headless: A Sleepy Hollow Story (Web Video) / int_8e5c862
comment
Henry Hudson really did sail from Amsterdam on the Half Moon and land in what would become the Hudson Valley, where Dutch settlements like Sleepy Hollow were born, and really did disappear soon after a mutiny while traveling north. But his wife's name was Katherine rather than Henrietta, she never captained a ship, and there were no other ships on the voyage with Henry in general. He also neither founded nor named anyone the mayor of Sleepy Hollow. It later turns out that "Henry Hudson as founder" is an Ancient Conspiracy in the Headless universe, with the real founder being Henrietta Hudson. This became a Suppressed History when she was cursed to become the Headless Horseman.
 Headless: A Sleepy Hollow Story (Web Video) / int_8e5c862
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Asshole Victim
 Headless: A Sleepy Hollow Story (Web Video) / int_8ed5c6e4
comment
Asshole Victim: Douffe gets stabbed in Episode 3, having been a generally unpleasant Rich Bitch who constantly raised Ichabod's rent for unfair reasons and tried to take something that wasn't hers as collateral. Helps that she's Only Mostly Dead. Devlyn Versace, Bad Influencer prankster died not once, but twice — first, in the middle of a prank while bungee jumping out of a blimp, and second via head-melting after humiliating Ichabod and leaving him unable to defend himself in court. Jonathan Oldstyle killed Diedrich to take his spot as Sleepy Hollow's bard. Some would say it serves him right to get stabbed in turn, even if he was doing it to help the heroes.
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 Headless: A Sleepy Hollow Story (Web Video) / int_963aab4a
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Speaking Up for Another
 Headless: A Sleepy Hollow Story (Web Video) / int_963aab4a
comment
Speaking Up for Another: Matilda gets pissed at Brom after he sabotaged Ichabod's trial out of jealousy, pointing out how he's just being a bully again. This leads to Brom's Heel Realization (done in the form of a Back to the Future Shout-Out, where he realizes he's been more of a Biff than a Marty).
 Headless: A Sleepy Hollow Story (Web Video) / int_963aab4a
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Orphan's Plot Trinket
 Headless: A Sleepy Hollow Story (Web Video) / int_9673d7f0
comment
Orphan's Plot Trinket: Ichabod, who was orphaned as a child, carries a mysterious necklace that his late grandmother left him that is connected to his origins in Sleepy Hollow.
 Headless: A Sleepy Hollow Story (Web Video) / int_9673d7f0
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 Headless: A Sleepy Hollow Story (Web Video) / int_972142db
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Headless Horseman
 Headless: A Sleepy Hollow Story (Web Video) / int_972142db
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Headless Horseman: The figure is a huge presence in the series.
 Headless: A Sleepy Hollow Story (Web Video) / int_972142db
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 Headless: A Sleepy Hollow Story (Web Video) / int_97926168
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Rewatch Bonus
 Headless: A Sleepy Hollow Story (Web Video) / int_97926168
comment
Rewatch Bonus: Knowing Kat's true intentions puts all of her scenes in a different light. Was she truly helping the Headless investigation at any point, or was she simply leading Ichabod astray the whole time? Matilda as well.
 Headless: A Sleepy Hollow Story (Web Video) / int_97926168
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Ridiculously Alive Undead
 Headless: A Sleepy Hollow Story (Web Video) / int_991a3be9
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Ridiculously Alive Undead: Each of the Horseman's Heads is exactly as they were in life, able to eat, drink, and get killed again. Kat, likewise, appears as a seemingly normal human being — no one suspects she died until Ichabod and Brom find her death certificate. Kat references this.
 Headless: A Sleepy Hollow Story (Web Video) / int_991a3be9
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Character Blog
 Headless: A Sleepy Hollow Story (Web Video) / int_9ae0cca6
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Character Blog: The whole series is essentially this for Brom's Babes.
 Headless: A Sleepy Hollow Story (Web Video) / int_9ae0cca6
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Marriage of Convenience
 Headless: A Sleepy Hollow Story (Web Video) / int_9b34ee31
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Surprisingly averted with Brom and Matilda. While the marriage only happened to avoid getting caught snooping and they can't even manage to fake kiss each other, Brom happily fetches groceries for Matilda, calls her "wifey", and frames their marriage license. Matilda does not object.
 Headless: A Sleepy Hollow Story (Web Video) / int_9b34ee31
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AcCENT upon the Wrong SylLABle
 Headless: A Sleepy Hollow Story (Web Video) / int_9b57f005
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Accent Upon The Wrong Syllable: The Babes debate over the proper pronunciation of "Biopic".
 Headless: A Sleepy Hollow Story (Web Video) / int_9b57f005
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SensualSlav
 Headless: A Sleepy Hollow Story (Web Video) / int_a0e1b552
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Sensual Slav: Lucretia, after revealing herself as the Lithuanian spy Oksana, becomes incredibly flirty with her former flame Paulie Tahoe.
 Headless: A Sleepy Hollow Story (Web Video) / int_a0e1b552
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Scenery Dissonance
 Headless: A Sleepy Hollow Story (Web Video) / int_a87b7e81
comment
Scenery Dissonance: The episodes, discussing spooky supernatural phenomena, are shot in a bright pink room with a teddy bear. Lampshaded and justified — it was the only studio available.
 Headless: A Sleepy Hollow Story (Web Video) / int_a87b7e81
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Adaptational Jerkass
 Headless: A Sleepy Hollow Story (Web Video) / int_a91078ea
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Adaptational Jerkass: The whole town, in a sense — the original Ichabod was well-liked by townspeople other than Brom and his group, while here Ichabod faces friction at every turn.
 Headless: A Sleepy Hollow Story (Web Video) / int_a91078ea
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Idiosyncratic Episode Naming
 Headless: A Sleepy Hollow Story (Web Video) / int_ac4ac8e5
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Idiosyncratic Episode Naming: Each episode has one of these, such as "Ghosts in the Graveyard" and "The Briny Booty". See Alliterative Title.
 Headless: A Sleepy Hollow Story (Web Video) / int_ac4ac8e5
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 Headless: A Sleepy Hollow Story (Web Video) / int_af4d6174
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Setting Update
 Headless: A Sleepy Hollow Story (Web Video) / int_af4d6174
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Setting Update: The original short story was set in 1790, while the web series is set over 200 years later. This also necessitates Ichabod needing a roommate, since in the 1790s school teachers were allowed to lodge in townsfolks' homes.
 Headless: A Sleepy Hollow Story (Web Video) / int_af4d6174
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Love Triangle
 Headless: A Sleepy Hollow Story (Web Video) / int_b7e0c5ff
comment
Love Triangle: As in the original, both Ichabod and Brom show interest in Kat. However, Kat initially pays neither of them any mind, and already dated Brom once when they were younger. As she shows increasing interest in Ichabod, Brom's jealousy gets worse. It turns out Kat was playing Ichabod in order to get him to be her sacrifice, so she wasn't actually interested in either of them .
 Headless: A Sleepy Hollow Story (Web Video) / int_b7e0c5ff
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Adaptational Backstory Change
 Headless: A Sleepy Hollow Story (Web Video) / int_ba46585b
comment
Adaptational Backstory Change: While he's still a school teacher, prior to moving to Sleepy Hollow, this Ichabod took care of his grandmother until her passing. He was also born in Sleepy Hollow, and has returned to find answers about his family, particularly the Orphan Plot Trinket his grandmother left him. Katrina Van Tassel is mostly a Flat Character who never left Sleepy Hollow and is implied to have her family in tact, but Kat briefly went away to college before dropping out and returning home to do odd jobs, and lost her mom when she was 10. She is later revealed to have been accidentally poisoned a year prior to the series, and got close to Ichabod only to use his life force to extend hers. Headless is revealed to not be a Revolutionary War Hessian mercenary, as is widely believed by the town. The Horseman is actually Henrietta Hudson, a witch and the town founder who predates the Revolutionary War by over a century.
 Headless: A Sleepy Hollow Story (Web Video) / int_ba46585b
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 Headless: A Sleepy Hollow Story (Web Video) / int_bee8baee
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Faint in Shock
 Headless: A Sleepy Hollow Story (Web Video) / int_bee8baee
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Judy also Faints in Shock when she sees Headless for the first time, despite being told about it in advance.
 Headless: A Sleepy Hollow Story (Web Video) / int_bee8baee
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 Headless: A Sleepy Hollow Story (Web Video) / int_c2393191
type
Show Within a Show
 Headless: A Sleepy Hollow Story (Web Video) / int_c2393191
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Show Within a Show: Unsolved Babesteries exists as a series within the Headless universe.
 Headless: A Sleepy Hollow Story (Web Video) / int_c2393191
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 Headless: A Sleepy Hollow Story (Web Video) / int_c25b1a4
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Life Drinker
 Headless: A Sleepy Hollow Story (Web Video) / int_c25b1a4
comment
The spell keeping Kat sustained from Rip Van Winkle's life-force only lasts for a year at a time, so she has to find a new host. Kat doesn't get the chance, however, since Headless getting their head back destroys the ivy that is essential to the spell, killing her instantly.
 Headless: A Sleepy Hollow Story (Web Video) / int_c25b1a4
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Cliffhanger
 Headless: A Sleepy Hollow Story (Web Video) / int_c6b8d37a
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In Episode 3, Captain Crowbones stabs Douffe in the abdomen, leaving Ichabod to faint deadaway. Cut to credits.
 Headless: A Sleepy Hollow Story (Web Video) / int_c6b8d37a
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Shout-Out
 Headless: A Sleepy Hollow Story (Web Video) / int_c75df49a
comment
Shout-Out: In "Max Lee", Max mentions a type of weed called "Rancho Cucamonga" which is grown in springtime. This is a reference to a lyric from a song Mary Kate Wiles sang as part of her work on The Fairly Oddparents Fairly Odder. Tripp and Blair sing a rendition of "Every Rose Has Its Thorn", with lyrics changed to suit the show. Tripp and Blair quote a line from "It's Quiet Uptown" from Hamilton and from "Wake Me Up Inside" by Evanescence while talking to Spike in the finale. Spike apparently had a thing for Kate Bush and Amy Lee back in the day.
 Headless: A Sleepy Hollow Story (Web Video) / int_c75df49a
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Power Trio
 Headless: A Sleepy Hollow Story (Web Video) / int_ca85e684
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Power Trio: The Babes themselves act as the central characters. See Four-Man Band and Three Plus Two for the alternate configurations.
 Headless: A Sleepy Hollow Story (Web Video) / int_ca85e684
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Dating Service Disaster
 Headless: A Sleepy Hollow Story (Web Video) / int_cc7a0386
comment
Dating Service Disaster: Douffe and Geoffrey apparently catfished each other prior to getting married. Douffe is implied to have used a picture of Bonnie Hunt for her profile picture.
 Headless: A Sleepy Hollow Story (Web Video) / int_cc7a0386
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Connected All Along
 Headless: A Sleepy Hollow Story (Web Video) / int_d1d1f420
comment
Connected All Along: Ichabod is the descendent of the witch who cursed the Headless Horseman. The Horseman's head is what generated the ivy keeping Kat alive. The Woman in White is heavily implied to be Kat's mother — or was when Spike saw the Woman back in high school.
 Headless: A Sleepy Hollow Story (Web Video) / int_d1d1f420
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type
What the Hell, Hero?
 Headless: A Sleepy Hollow Story (Web Video) / int_d39e327f
comment
What the Hell, Hero?: Spike gives one to the Babes at the end of Episode 2, wondering who this attempt at reconciliation is even for. Unfortunately, it doesn't stick for the babes.
 Headless: A Sleepy Hollow Story (Web Video) / int_d39e327f
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Race Lift
 Headless: A Sleepy Hollow Story (Web Video) / int_d7c3ba61
comment
Race Lift: Since the Irving stories were based in the white Dutch colonies of post-Revolutionary upstate New York, the modern adaptation took this approach to a number of characters: White Anglo-Saxon Protestant Ichabod Crane is played by Indian-American Sean Persaud. Rip Van Winkle and Judy Gardenier are played by African-American actors James Tolbert and Krystina Arielle. Douffe Martling is played by Hawaiian actress Joanna Sotomura.
 Headless: A Sleepy Hollow Story (Web Video) / int_d7c3ba61
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Company Cross References
 Headless: A Sleepy Hollow Story (Web Video) / int_d9e48d0
comment
Company Cross References: The Freeze-Frame Bonus of "American Whoopee 95th Anniversary Criterion..." video thumbnail in "The Chaos in Court". The chalkboard in the police precinct in "The Clues in the Clink" has the words, "DON'T DO MURDER!" on it, a quote from the cop characters from Edgar Allan Poe's Murder Mystery Dinner Party.
 Headless: A Sleepy Hollow Story (Web Video) / int_d9e48d0
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Red Herring
 Headless: A Sleepy Hollow Story (Web Video) / int_dbca2c99
comment
Red Herring: Cotton Van Tassel is revealed to be the only person on record who was beheaded in Sleepy Hollow around the time Headless supposedly showed up in the late 1700s, seeming to signal he was the one who became Headless. But Kat and Ichabod discover that Cotton's body and head were cremated together, before evidence turns up that Headless was spotted as far back as 1622. Max Lee describes the Woman in White as a blonde woman. Between her blonde hair and wearing a lot of white, Kat was suspected to be connected to the Woman in White, if not the Woman herself. However, Spike later reveals he saw her as a redheaded woman, heavily implying that the Woman in White at some point became Kat's Missing Mom.
 Headless: A Sleepy Hollow Story (Web Video) / int_dbca2c99
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type
Contrived Coincidence
 Headless: A Sleepy Hollow Story (Web Video) / int_dc579c91
comment
Contrived Coincidence: The skull inside Colonial Drugs 'n' Stuff that Ichabod decides to use first just happens to be that of Captain Gravy Davy Crowbones, who just happens to hold the diary and Plot Trinket that help reveal the Horseman's identity. Ichabod picks Anne Tarry's skull at random from a bag, whose death had something to do with Baltus Van Tassel. Both of the above are justified slightly, since Henrietta indicates Ichabod was drawn to Sleepy Hollow and was meant to reunite Henrietta with her head, so there may be something magical at work with these events. Internationally-renowned thief Paulie Tahoe just happened to be buried in the same sleepy New York town that his former protege and lover Oksana was forced to move to as part of Witness Protection, and Oksana/Lucretia just so happened to be the mark for the One Last Job he is asked to pull.
 Headless: A Sleepy Hollow Story (Web Video) / int_dc579c91
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 Headless: A Sleepy Hollow Story (Web Video) / int_dcbe8a6e
type
Chekhov's Gunman
 Headless: A Sleepy Hollow Story (Web Video) / int_dcbe8a6e
comment
Chekhov's Gunman: Gravy Davy Crowbones seems like just one of the many guest-star heads, but his treasure chest ends up holding the literal and figurative keys to the mystery of the Horseman. (See Chekhov's Gun above). In the Trousers' history play, Henrietta Hudson is only given a passing mention. She is in fact the true identity of the Horseman, and the true founder of the town. The Woman in White is also given a passing mention in the town history play. Not only is she the reason for Spike's childhood trauma, but she may be the answer to what happened to Kat's mom.
 Headless: A Sleepy Hollow Story (Web Video) / int_dcbe8a6e
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 Headless: A Sleepy Hollow Story (Web Video) / int_dd5faec5
type
Only Mostly Dead
 Headless: A Sleepy Hollow Story (Web Video) / int_dd5faec5
comment
Only Mostly Dead: Douffe is left in a coma after getting stabbed in the gut by Gravy Davy Crowbones' sword. Ichabod fears she will wake up and accuse him of murder.
 Headless: A Sleepy Hollow Story (Web Video) / int_dd5faec5
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 Headless: A Sleepy Hollow Story (Web Video) / int_deecc9eb
type
Awful Wedded Life
 Headless: A Sleepy Hollow Story (Web Video) / int_deecc9eb
comment
Awful Wedded Life: Geoffrey hates being married to Douffe, especially since she catfished him, so much so that he celebrates with champagne when the divorce papers finally go through... while Douffe is still in a coma. Surprisingly averted with Brom and Matilda. While the marriage only happened to avoid getting caught snooping and they can't even manage to fake kiss each other, Brom happily fetches groceries for Matilda, calls her "wifey", and frames their marriage license. Matilda does not object.
 Headless: A Sleepy Hollow Story (Web Video) / int_deecc9eb
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 Headless: A Sleepy Hollow Story (Web Video) / int_e16217f8
type
Historical Villain Upgrade
 Headless: A Sleepy Hollow Story (Web Video) / int_e16217f8
comment
Historical Villain Upgrade: Henry Hudson orchestrated his wife's curse, alongside her fellow witch Anneke Storms, out of jealousy.
 Headless: A Sleepy Hollow Story (Web Video) / int_e16217f8
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 Headless: A Sleepy Hollow Story (Web Video) / int_e563bf09
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Insistent Terminology
 Headless: A Sleepy Hollow Story (Web Video) / int_e563bf09
comment
Insistent Terminology: Colonial Drugs 'N' Stuff is called "Not-a-drugstore" by its employees.
 Headless: A Sleepy Hollow Story (Web Video) / int_e563bf09
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Headless: A Sleepy Hollow Story (Web Video) / int_e563bf09
 Headless: A Sleepy Hollow Story (Web Video) / int_eb7c34cf
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Crossover
 Headless: A Sleepy Hollow Story (Web Video) / int_eb7c34cf
comment
Crossover: Rip Van Winkle Jr. and Judy Gardenier (originally Judith Van Winkle Gardenier) are characters from Irving's other famous short story, "Rip Van Winkle", while Diedrich Knickerbocker traces back to Irving's first major book, A History of New York, and served as Irving's Pen Name / Direct Line to the Author set up for that work, as well as for "Rip Van Winkle".
 Headless: A Sleepy Hollow Story (Web Video) / int_eb7c34cf
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 Headless: A Sleepy Hollow Story (Web Video)
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Headless: A Sleepy Hollow Story (Web Video) / int_eb7c34cf
 Headless: A Sleepy Hollow Story (Web Video) / int_eb857152
type
Quirky Town
 Headless: A Sleepy Hollow Story (Web Video) / int_eb857152
comment
Quirky Town: With its cursed bog, not-a-drugstore, and supernatural local legends, Sleepy Hollow qualifies.
 Headless: A Sleepy Hollow Story (Web Video) / int_eb857152
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Two-Teacher School
 Headless: A Sleepy Hollow Story (Web Video) / int_edce12ef
comment
Two-Teacher School: The only current teachers we meet from Sleepy Hollow Middle School are Ichabod and Brom, with the only other teacher mentioned being Ichabod's predecessor.
 Headless: A Sleepy Hollow Story (Web Video) / int_edce12ef
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 Headless: A Sleepy Hollow Story (Web Video)
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 Headless: A Sleepy Hollow Story (Web Video) / int_f0508c08
type
Decomposite Character
 Headless: A Sleepy Hollow Story (Web Video) / int_f0508c08
comment
Decomposite Character: Downplayed. While it is implied but never confirmed that Brom dressed up as the Headless Horseman to scare Ichabod in the original story, here the Horseman is definitely supernatural and definitely a separate character from Brom.
 Headless: A Sleepy Hollow Story (Web Video) / int_f0508c08
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 Headless: A Sleepy Hollow Story (Web Video)
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 Headless: A Sleepy Hollow Story (Web Video) / int_f7a1c539
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Three Plus Two
 Headless: A Sleepy Hollow Story (Web Video) / int_f7a1c539
comment
Three Plus Two: The Babes when working with Eugene and Ramona Trousers act as this, with the Trousers' artistic integrity counteracting the Babes' tendency to get off track.
 Headless: A Sleepy Hollow Story (Web Video) / int_f7a1c539
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Running Gag
 Headless: A Sleepy Hollow Story (Web Video) / int_f9f2c33
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Running Gag: Headless's ridiculous disguises. Ichabod only uses Bing. Matilda and Brom think that's gross.
 Headless: A Sleepy Hollow Story (Web Video) / int_f9f2c33
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Undeath Always Ends
 Headless: A Sleepy Hollow Story (Web Video) / int_fb23483d
comment
Undeath Always Ends: The heads only last 24 hours with mugwort, though they can be killed again sooner. The spell keeping Kat sustained from Rip Van Winkle's life-force only lasts for a year at a time, so she has to find a new host. Kat doesn't get the chance, however, since Headless getting their head back destroys the ivy that is essential to the spell, killing her instantly.
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 Headless: A Sleepy Hollow Story (Web Video) / int_fd94c4ac
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Theme Naming
 Headless: A Sleepy Hollow Story (Web Video) / int_fd94c4ac
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Theme Naming: Each episode is named after one of the Heads, except for the last one, which is "Clip Show".
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 Headless: A Sleepy Hollow Story (Web Video)
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 Headless: A Sleepy Hollow Story (Web Video) / int_fdb355db
type
Fun with Subtitles
 Headless: A Sleepy Hollow Story (Web Video) / int_fdb355db
comment
Fun with Subtitles: Turning on English Closed Caption on Youtube reveals fun descriptions such as: *A spooky, somewhat sinister, jaunty musical cue slowly builds... into the Headless theme. God, it's a bop* *Makes noises that can only be likened to a cat coughing up a hairball*
 Headless: A Sleepy Hollow Story (Web Video) / int_fdb355db
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 Headless: A Sleepy Hollow Story (Web Video) / int_fdb355db
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 Headless: A Sleepy Hollow Story (Web Video)
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 Headless: A Sleepy Hollow Story (Web Video) / int_fe0330fb
type
Brick Joke
 Headless: A Sleepy Hollow Story (Web Video) / int_fe0330fb
comment
Brick Joke: Matilda tells Ichabod in Episode 1 that the fake book in Not-a-Drugstore would be good for storing the still-beating hearts of your enemies... or an inhaler. Episode 2 shows Ichabod did buy the fake book and is storing his inhaler inside.
 Headless: A Sleepy Hollow Story (Web Video) / int_fe0330fb
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Four-Man Band
 Headless: A Sleepy Hollow Story (Web Video) / int_fe3bf3a4
comment
Four-Man Band: Played with — while Spike is both the Only Sane Man and The Smart Guy, the other three are so similar in personality they're almost the same person, so there isn't much of an interplay of personalities. One could make a case for Tripp (who has an archaeology degree) being The Smart Guy, but it would be a stretch. Spike is also distant from the Babes, communicating by Zoom, downplaying their dynamic.
 Headless: A Sleepy Hollow Story (Web Video) / int_fe3bf3a4
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Headless: A Sleepy Hollow Story (Web Video)

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 Headless: A Sleepy Hollow Story (Web Video)
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 Headless: A Sleepy Hollow Story (Web Video)
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 Headless: A Sleepy Hollow Story (Web Video)
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