History WebVideo / HeadlessASleepyHollowStory

* OrphansPlotTrinket: Ichabod, who was orphaned as a child, carries a mysterious necklace that his late grandmother left him [[spoiler: connected to his origins in Sleepy Hollow]].

* LoveTriangle: 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. [[spoiler: It turns out Kat was playing Ichabod in order to get him to be her sacrifice, so ''both'' men were delusional.]]

** Brom, the Babes, and Spike, are also implied to be this, since they've all known each other since at least high school.

** Geoffrey hates being married to Douffe, especially since she catfishes him, so much so that he celebrates with champagne when the divorce papers finally go through... [[spoiler: while Douffe is still in a coma]].

** ''A Brief History of Sleepy Hollow'' is an annual play put on by the Trousers, mostly full of inaccuracies and * StylisticSuck.

** ''A Brief History of Sleepy Hollow'' is an annual play put on by the Trousers, mostly full of inaccuracies and StylisticSuck.

* SpeakingUpForAnother: Matilda gets pissed at Brom after he sabotaged Ichabod's trial out of jealousy, pointing out how he's [[ReformedBully just being a bully again]]. This leads to Brom's HeelRealization (done in the form of a ''Franchise/BackToTheFuture'' ShoutOut, where he realizes he's been more of a Biff than a Marty).

** The Headless Horseman is usually the antagonist trying to scare/murder Ichabod in DerivativeWorks/SleepyHollow media. Here, they are just roommates who must work together to find the horseman's head.

** Prior to moving to Sleepy Hollow, this Ichabod took care of his grandmother until her passing. [[spoiler: He was also born in Sleepy Hollow, and has returned to find answers about his family, particularly the OrphanPlotTrinket his grandmother left him.]]

** The Headless Horseman is usually the antagonist trying to scare/murder Ichabod in Franchise/SleepyHollow media. Here, they are just roommates who must work together to find the horseman's head.

''Headless: A Sleepy Hollow Story'' is a 2022 modern web series adaptation of the Creator/WashingtonIrving short story "Literature/TheLegendOfSleepyHollow", by WebVideo/ShipwreckedComedy. 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 HeadlessHorseman. 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.

** "[[Film/NightOfTheLivingDead Night of the Living]] [[PunnyName Bread Bowl]] Tortilla Soup".

* SpeakingUpForAnother: Matilda gets pissed at Brom after he sabotaged Ichabod's trial out of jealousy, pointing out how he's [[ReformedBully just being a bully again]]. This leads to Brom's HeelRealization (done in the form of a ''Film/BackToTheFuture'' ShoutOut, where he realizes he's been more of a Biff than a Marty).

** Gravy Davy Crowbones seems like just one of the many guest-star heads, [[spoiler: but his treasure chest ends up holding the literal key to the mystery of the Horseman.]]

''Headless: A Sleepy Hollow Story'' is a 2022 modern web series adaptation of the Creator/WashingtonIrving short story "Literature/TheLegendOfSleepyHollow", by WebVideo/ShipwreckedComedy. 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 must become roommates with the HeadlessHorseman. 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.

** 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.
*** [[spoiler: It later turns out that "Henry Hudson as founder" is an AncientConspiracy in the ''Headless'' universe, with the real founder being Henrietta Hudson. This became a SuppressedHistory when she was cursed to become the Headless Horseman.]]

** [[spoiler: Max Lee describes the Woman in White as a blonde woman. Between the blonde hair and Kat wearing a lot of white, many suspected she was the true Woman in White. However, Spike later reveals he saw her as a redheaded woman, heavily implying that the Woman in White at some point became Kat's ''mom''.]]

--> '''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.