Web Video / Headless: A Sleepy Hollow Story

Deep in the forest where ghouls haunt and wallow
There's a town by the name of Sleepy Hollow
It's drowsy and dreamy, and filled with dread
They'll warn you: "Be wary of all those things dead!"
And just when you're sure you're safe asleep in your bed,
You might come 'cross a fellow who's lost his head...

— Opening lyrics

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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This work contains examples of the following tropes:

• 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.
• 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.
• 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.
• 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.
• 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.
• Adaptational Personality Change:
  • Ichabod in the original story, while the schoolmaster, had a strong belief in the supernatural (which was fairly common in the 1800s, when the story took place). In the web series he is a skeptical science teacher who is forced to believe when faced with the weirdness of the town.
  • 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.
• 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.
• 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.
• Alliterative Title: Each episode has one of these, such as "Ghosts in the Graveyard" and "The Briny Booty". See Idiosyncratic Episode Naming.
• Animated Credits Opening: Starting in Episode 2, the opening credits are animated.
• 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).
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
  Judy: So don't like use them as coasters or get any of your fake blood on 'em. (to Verla) I'm talking to you, Missy.
  Verla: It wasn't fake.
  [Awkward pause]
• 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.
• 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.
  Spike: Did Versace's brief recurrence on this earth help solve the mystery [of the Horseman's head], or was it merely a comedic interlude while the plot thickened around our hero like Devlyn's yummy stew...? (grabs script page) Who wrote this?!
• 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.
• Character Blog: The fictionalized version of Sleepy Hollow from the show has an Instagram page. In addition, access to Ichabod, Kat, Matilda, and Brom's Instagrams was one of the exclusive Kickstarter backer perks.
• Chekhov's Gun:
  • In Episode 3, Gravy's sword is initially played for laughs, but he ends up stabbing Douffe with it at the end of the episode. He also recovers a small chest of his treasures, which include a necklace and sea log. The necklace unlocks the door to the basement of Storms' Inn, where Anneke Storms died, while the sea log reveals that the Horseman existed long before the Revolutionary War.
  • The photograph of Kat's mom with young Kat and Matilda was taken at the wreck of the Liechtgevund, revealing that Henrietta Hudson made it to Sleepy Hollow.
  • The ivy shown throughout the Old Dutch Church in Episode 4, which Max attempts to smoke, is the key component to the spell keeping Kat alive and an indicator that Headless's head was there all along.
  • The paper used for Matilda and Brom's marriage certificate is part of an old map which leads Brom to the head's location.
  • Matilda says Baltus's checkbook with checks made out to Dr. Crayon is just a sign that Baltus needs pills to handle Judy's energy. It's actually evidence that Baltus was giving shush money to Crayon to cover up Kat's death. Matilda knew this and purposely dismissed it so Brom would not suspect.
• 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.
• 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.
• Cliffhanger:
  • Episode 1 ends with Brom and Ichabod meeting the Horseman, who appears ready to attack... before holding out Ichabod's roommate flyer.
  • Episode 3 ends with Gravy stabbing Douffe, causing Ichabod to faint.
  • Episode 5 ends with Anne Tarry revealing Baltus Van Tassel, the mayor and Kat's father, killed her, just after Baltus has invited Ichabod to dinner.
  • Episode 7 ends with Douffe, now awake, confronting Ichabod and Kat, while Matilda resurrects Paulie Tahoe for a heist.
  • Episode 8 ends with Headless (as Paulie) escaping with Douffe, while the trio gets cornered by Officer Meinhof and Mayor Van Tassel.
  • Episode 9 ends with the reveal that Kat's legally been dead for over a year.
• 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.
• 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.
• 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.
• 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.
• 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".
• 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.
• 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.
• 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.
• 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.
• 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.
• 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"
• 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.
• 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*
• Gilligan Cut:
  • In Episode 2:
    Ichabod: Brom, she can't just wave her magic wand and attach a head to him.
    [cut]
    Matilda: Sure, I'll just wave my magic wand and attach a head to him.
  • 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 Horseman: The figure is a huge presence in the series.
• 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.
• Historical Villain Upgrade: Henry Hudson orchestrated his wife's curse, alongside her fellow witch Anneke Storms, out of jealousy.
• 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.
• Idiosyncratic Episode Naming: Each episode has one of these, such as "Ghosts in the Graveyard" and "The Briny Booty". See Alliterative Title.
• Insistent Terminology: Colonial Drugs 'N' Stuff is called "Not-a-drugstore" by its employees.
• 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?"
• 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 .
• 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.
• 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.
• Nepotism: Implied, since pretty much every mayor mentioned in the series since the town's founding has been a Van Tassel.
• 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.
• 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.
• 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.
• 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.
• Power Trio: Ichabod, Matilda, and Brom band together to help Headless find his head. This sometimes turns into Four-Man Band, depending on Headless's personality, and Three Plus Two after Kat is let in on the secret.
• 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.
• Quirky Town: With its cursed bog, not-a-drugstore, and supernatural local legends, Sleepy Hollow qualifies.
• 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.
• 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.
• 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.
• Related in the Adaptation: Douffe Martling and Geoffrey Crayon are a married couple (though both were apparently catfished into it). They later get divorced.
• 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.
  Ichabod: Sorry, Kat. My uncle has to —
  Kat: I thought you said he was your cousin?
  Ichabod: I have a weird family!!
• 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.
• 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.
• Running Gag:
  • Headless's ridiculous disguises.
  • Ichabod only uses Bing. Matilda and Brom think that's gross.
• Sensual Slav: Lucretia, after revealing herself as the Lithuanian spy Oksana, becomes incredibly flirty with her former flame Paulie Tahoe.
• 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.
• 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.
• Shout-Out:
  • "Night of the Living Bread Bowl Tortilla Soup".
  • Brom considers himself the Marty McFly of his own life, and calls Matilda "Sabrina the Not-So-Teenage Witch" in one episode.
  • The slime Ichabod gets covered in during Episode 5 looks very much like Nickelodeon Slime.
  • From the Sleepy Hollow Instagram page, Judge Pringle's reaction video to My Cousin Vinny became an Instant Web Hit.
• Show Within a Show:
  • A Brief History of Sleepy Hollow is an annual play put on by the Trousers, mostly full of inaccuracies and Stylistic Suck.
  • See Unsolved Babesteries below.
• 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).
• 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.
• 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.
• 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.
• 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.
• Weird Trade Union: Diedrich is part of the Bards' Union, which requires a four-hour break every 30 minutes.
• Wham Line:
  • In Episode 5,
  Matilda: You're Anne Tarry. (to Ichabod) This is Baltus's assistant before Judy.
  Anne: Yeah, I was. Before he killed me.
  • In Episode 9,
  Ichabod: It's a death certificate.[...] For Kat. It says she died a year ago.
• 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.
• Witness Protection: Lucretia turns out to be in this, as she is actually international super spy Oksana Bolshekov.
• Wolf in Sheep's Clothing: Kat and Baltus. Kat gets close to Ichabod in hopes of using him to extend her life another year, while Baltus covers up what he did to Kat, Anne, and Rip by paying off Dr. Crayon, and is willing to kill Judy as well.
• X Meets Y: Sleepy Hollow is described in the Kickstarter as "Pushing Daisies meets Schitt's Creek, with a dash of A Series of Unfortunate Events".

Unsolved Babesteries-Specific Tropes

• Accent Upon The Wrong Syllable: The Babes debate over the proper pronunciation of "Biopic".
• Character Blog: The whole series is essentially this for Brom's Babes.
• Clip Show: Parodied and lampshaded. The series finale takes the form of one, even though Cal points out it's hard to have a clip show when the show itself only runs 30 minutes. They make do.
• Companion Show: Serves as one to Headless, showing the Babes' perspective of certain events and providing some clues to the overall mystery.
• Denser and Wackier: Headless may be quirky, but Unsolved Babesteries is a whole other level of silly.
• 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".
• 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.
• 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.
• 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."
• Mockumentary: Filmed in a documentary style following the events of the Headless series from the Babes' perspective (with Ramona and Eugene pitching in).
• Power Trio: The Babes themselves act as the central characters. See Four-Man Band and Three Plus Two for the alternate configurations.
• 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.
• 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.
• 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.
• Show Within a Show: Unsolved Babesteries exists as a series within the Headless universe.
• Stylistic Suck: The opening credits have a very homemade quality, and there are multiple sections shot from a camera phone.
• Theme Naming: Each episode is named after one of the Heads, except for the last one, which is "Clip Show".
• 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.
• Wham Line: "Wait... Spike saw the [Woman in White] after Kat's mom went missing."
• 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.

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