The Headless Horseman

**The Headless Horseman** is the secondary protagonist in *Headless: A Sleepy Hollow Story*. Throughout the series, they work with Ichabod Crane, their roomate, to discover who its true head is. As they try on different heads, they take on different personalities.

This page mainly focuses on the Headless Horseman in its "normal" form. There are brief details about the various lives it takes on, but, to learn more about those people and their actions in the show, you should visit their individual pages.

## Personality

The Horseman is a friendly, curious, and reassuring person. They might be slightly forgetful and unaware of some social rules, but they always try their best. They try to help out Ichabod Crane when they can. One of the ways they help is with their vast knowledge of history.

## Background

According to Brom Bones, the Headless Horseman is an aggro Hessian mercenary hired by the Brits to fight during the Revolutionary War. He was decapitated on the battlefield and wanders the woods at night, unable to pass on until he is reunited with his head. However, details revealed in Headless question this validity.

By the end of Episode Ten, we learn the truth. The Headless Horseman was actually created when Anneke Storms worked with others to behead Henrietta Hudson. After this, she haunted the town and tried to be reunited with her head. Over the course of 400 years, she takes on many different jobs and learns many different things.

Elizabeth Van Tassel tried to theorize and confirm the true orgins of the Horseman, but no one would believe her. Ultimately, closure for the journey of the Headless Horseman and Henrietta Hudson happen at the end of the Headless Series.

## Events of *Headless: A Sleepy Hollow Story*

At the end of Episode One, the Horseman rides in on a steed and scares Ichabod Crane and Brom Bones. They hold out a "roommate poster" that Ichabod had put up earlier. Through a game of charades, the Horseman explains that they will help Ichabod pay rent, if he helps them find their head. They need to do so quickly because the longer they wait, the more the Horseman forgets. Ichabod is in a desperate situation, so he agrees to the deal.

During Ichabod's first day at school, the Horseman hides in the classroom closet. Once the bell rings, they emerge and scare Brom. Brom and Ichabod try to temporarily use a pumpkin with a smiley face instead of a head. But, they need a more permanent solution. So, the trio heads to Matilda Bishop, the town witch, for help. She manages to come up with a spell that will allow the Horseman to take on the personality and form of whosever head they are wearing. To begin, they try Verla Wolfson's "boyfriend's" head, Henri. For a brief moment, Henri comes alive. However, the magic spell quickly undoes itself, and it is back to only being the Headless Horseman. In need of more skulls, the Headless Horseman, Ichabod, Brom, and Matilda decide to try hunting for some in the graveyard. They are stopped when Officer Baader Meinhof finds Ichabod trespassing and gives him a court date. Luckily, the Horseman scares off the Officer and hugs Ichabod before things escalate too far.

The next day, the Horseman (with a pink parasol) and Ichabod head to tell Matilda the news. She does not have any new skulls, but she has managed to perfect the spell with the help of mugwort so that they can take on the form of a skull for a full day. Ichabod is desperate to put a new head on the Horseman before Kat Van Tassel arrives, so he looks around the store. He finds a skull that Matilda says, "came with the drugstore." The Headless Horseman wiggles their fingers mischievously before having the new head placed on. The cloud of smoke and magic dissipates to reveal Captain Gravy Davy Crowbones. A fearsome pirate who loves jewels, ale, his lover, and being unpredictable. He wreaks havoc on Kat and Ichabod's date, and he stabs Douffe Martling, Ichabod's (evil) landlady. Before anyone can catch the Captain, a day has passed and the Horseman is back to their headless form. The only thing the pirate leaves behind is a treasure chest.

The next time that the Headless Horseman ventures out with Ichabod, they use a masquerade mask as a disguise. Since their last visit, Matilda has found the head of a Revolutionary War soilder. When they cast the spell, they are shocked to see Max Lee, a Revolutionary War *reenactor*, come to life. He explains that he had had his grave altered because he loved history so much. The trio heads to watch the Sleepy Hollow history play being put on by the Trousers. Max Lee helps point out many factual inaccuracies in the play. This raises even more questions about the Horseman's past. After the play, Max walks with Ichabod, Brom, and Kat. Brom takes the opportunity to use Baphomet's eyelashes to dissolve the head off the Horseman in front of Kat. His goal is to scare her away, but she is very delighted to see that the Horseman is real. This puts a previously nervous Horseman at ease. Once Kat walks away, the Horseman tries to give Ichabod a high five and fails. As a favour, Ichabod asks Brom to find the next skull for the Horseman- a good lawyer.

Before Ichabod's court hearing, the Horseman sneaks in (using a plant as a disguise). They use the head from Brom to cast the spell. But, the Horseman does not take on the form of a good lawyer; they take on the form of Devlyn Versace. The Horseman is overcome with making terrible Youtube streamer pranks and jokes. During the session, Matilda works with Kat, Brom, and Verla to look for other people the Horseman might be. Through old documents, they discover the only recorded person in the town with a beheading was Cotton Van Tassel who died in 1785. The lead on the identity of the Horseman is great! Sadly, not as great, is Ichabod's fate. Devlyn causes Ichabod to be given a sentence of 50 community service hours. When the others share this news with Ichabod, they choose to dissolve Devlyn. In her place, they put a new head.

The Horseman takes on the life of Anne Tarry, the mayor's last assistant. She is confused and shocked to be brought back to life. When she learns that Ichabod plans to have dinner with the Van Tassels, she insists on joining him in disguise. She joins the dinner as 'Mark' to help solve crimes. Mark's questions and comments worry Ichabod, but they open up new doors. They also confirm that the Headless Horseman is not Cotton Van Tassel because he was later reunited with his head and cremated.

Later, Brom and Ichabod go through Elizabeth Van Tassel's manuscript regarding the Headless Horseman. But, Matilda interrupts them because a new head has been put on. The Horseman has now taken on the form of the bad comedian Bruce McConnell. For better or worse, this head is quickly dissolved when a tomatoe is thrown at him and he dies.

The next day, the Horseman chills at Colonial Drugs 'N' Stuff and plays on a switch. The Horseman sets the switch down when the others enter and begin to put together more clues about the Horseman's past. The Horseman wiggles their fingers mischievously. Using *Bing* and the Horseman's book smarts, they have a break through. The Horseman's true skull is believed to be in the basement of Storms Inn. To get into the basement, there must be a heist. So, the Horseman takes on the form of Paulie Tahoe, a heist extraordinaire.

Paulie leads them to success, and they find treasure. Anneke Storms' old diary in the basement reveals that the Horseman is none other than Henrietta Hudson. They learn that Henrietta was beheaded by other members of her witch coven. In order to find her skull, they plan to place Anneke's skull on the horseman and have her guide them. But, they are all caught and put in jail. Shortly after Paulie enters the jail cell, the spell ends and he transforms back into the Horseman.

Eventually, Judy helps Kat break the Horseman and others out. The Horseman waves at Judy, and she is so suprised that she faints. She quickly recovers. They find Anneke's skull in the Officer's office. But, when they go to put it on, Kat drops it, and it shatters on the floor. They look over the diary again in another attempt to find Henrietta's skull for the Horseman. While the search for clues continues, the Horseman walks arm and arm with Judy to the morgue. They try to look for a new skull that would be helpful. In the morgue, they find an unknown and fresh skull.

This time, Verla perfrorms the spell to unite the skull and Headless Horseman. The Horseman takes on the life of Diedrich Knickerbocker, and everyone is shocked. Almost immediately, Diedrich begins to fight the bard that killed him. During this scuffle, Ichabod disappears. Once the others and Diedrich notice, they quickly work to find Henrietta's skull, in hopes that it will lead them to Ichabod. However, Diedrich gives up quickly and decides they should just try to wrap it up with a song. Luckily, Brom stops him and connects the missing clues. Brom rushes into the church and gets tied up next to Ichabod by Kat and Matilda. Meanwhile, Diedrich sneaks in and hides in a dark corner.

Moments later, he uses the other bard as a distraction so that he can come into the open, sing a song, and free Ichabod and Brom. When the girls return, Ichabod asks a question to have the motives clarified; Diedrich steps in and sings a song about the past year of Kat's life. Once his song ends, Kat steps forward and stabs him. Thus, killing Diedrich Knickerbocker once more. In the background, the Headless Horsman takes on its 'normal' form and unsheathes their sword. They charge towards Kat. The two engage in a fight. Kat bests them, and she takes their sword. During the fight, Ichabod finds Henrietta's skull in the floor boards. However, he is forced to give it to Matilda. She is tight on time and forced to make a hard decision; against Kat's wishes, she chooses to toss the skull on the Horseman. Headless catches their head and places it on top in time for the natrual moon magic to take its course. In exchange, Matilda does not have time to cast the spell to save Kat, so she passes away.

They transform into their true form of Henrietta Hudson. She looks around the room, offers a few words, grabs her sword back, and kneels down next to Matilda. She takes the opportunity to offer comfort to Matilda and create flowers to place atop of Kat's chest. The group then leaves the church and walks in the woods. Henrietta tells them all information about their ancestors' pasts and her own past. She thanks Ichabod for all that he has done and represents. Then, she offers her sword, which has the word "GLORY" engraved in it, to him. As he takes it, she vanishes into thin air.

## Other Tidbits

* *Unsolved Babesteries* is a Headless Series companion series. In the series, Brom's Babes dig deeper into mysteries that sorround the Headless Horseman. They also reveal more about the past lives of the heads the Horseman takes on.
* Tom Detrinis, the "base" actor for the Horseman, can see through the white cravet mesh in the Horseman's costume.
* The costume was made by Morgan Gannes.
* The pumpkin with a smiley face that was momentarily used as a Headless Horseman head was found outside a Burbank, California coffee shop in Janurary, 2022. The real pumpkin had been leftover from Halloween, and the coffee shop let them keep it.
* In 1622, Captain Gravy Davy Crowbones saw the Headless Horseman on their steed.
* Mayor Baltus Van Tassel claims, "Well, you're not a true resident of Sleepy Hollow until you \*think\* you've seen [the Headless Horseman]."
* At one point, the Horseman pretends to be a Halloween decoration. They also wear a beret and pretend to be a drunk actor who lost their job at the Ren Faire. All of this is to avoid being caught.
* Stories about the Headless Horseman have been written about in many in-world literary ways including Elizabeth Van Tassel's books and the Trousers' two plays.
* During Shipwrecked's 2022 online auction, various Horseman related pieces were able to be bid on. There were skulls from various heads (sold for $100 and $105), pouches used to cast the spells (sold for $65 and $35),and the brooch worn by the heads (sold for $130).

1. ↑ 1.0 1.1 "The Iconic Pumpkin" short on Youtube
2. ↑ Episode Seven: The Secrets in the Sea Log
3. ↑ Episode Six: The Distractions at Dinner
4. ↑ Episode Two: The Ghosts in the Graveyard
5. ↑ Shipwrecked Comedy online auction on GalaBid