‘Headless: A Sleepy Hollow Story’: Felicia Day & Tom Lenk on Surprise Cameos, Finale Twists

[Warning: The below contains MAJOR spoilers for Headless: A Sleepy Hollow Story Season 1.]

After 10 weeks, the saga of Headless — the web series from Shipwrecked Comedy based on the famous Legend of Sleepy Hollow story — has finally come to an end, with some tantalizing reveals in the form of plot twists, cliffhangers, and special surprise guest stars.

“It’s been better than we envisioned,” creator Sean Persaud, who helmed the series with his sister, Sinead, tells TV Insider of the reception to the series since its premiere on August 29. “We worked really hard to sort of create this intricate story that kind of fit together and made sure that we planted clues and, you know, put stuff in there that people could get excited about and pick up on and people are responding to it really well. It’s been even more positive than we thought it would be.”

Nearly all of those clues set up over the course of the series paid off in the finale, which — spoiler alert! — dropped head-spinning reveals like love interest Kat Van Tassel (Mary Kate Wiles) actually being dead, her father Baltus Van Tassel (John Rubinstein) going to jail, and the identity of the Headless Horsemen being not a man, but a woman named Henrietta Hudson — as played by surprise guest star Felicia Day, best known for her work on The Guild and Supernatural.

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“I wanted to channel a badass woman and be the most competent in the room, also stretch myself from who I usually play, more quirky and comedic characters,” Day told us of Henrietta, who was the leader of a witch coven and subsequently killed by another witch named Anneke Storms. “I got great material to work with and had a blast pretending to know what I was doing!”

The second surprise guest star came in the form of Tom Lenk (Buffy the Vampire Slayer) who played bard Jonathan Oldstyle. For both Lenk and Day (who run a joint podcast called Undressing), the opportunity to play in Shipwrecked’s sandbox came to them pretty easily — as did their decision to say yes. “I just was impressed because I know Sean from having we did some 30-minute musical shows together,” Lenk said, adding that while he didn’t know his friend in “this capacity” (in other words, as a writer/producer), he was blown away by the work and professionalism on set. Day, for her part, had been familiar with Shipwrecked’s work thanks to being a fan of Wiles and was “thrilled to be able to be in a web series again after so many years away.”

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“I think the casting of Tom and Felicia are two of my favorite things that we did in the show,” Persaud acknowledged, while also acknowledging that their involvement, a secret until today’s episode drop, were two of the hardest secrets to keep. “The Horseman was a character that we mentioned a few times but we were unable to sort of establish visually, so we wanted to cast someone who had that power — you see that person, you’re like, ‘Oh, this is a big deal.’ And Felicia has that. She just carries that weight, especially with this sort of fandom.”

Lenk’s character, who quite literally “shows up out of nowhere” with his ukelele after the series’ original bard Diedrich Knickerbocker (Jon Cozart) dies, was one of Persaud’s favorite moments in the finale. “Tom has such an indescribable comedic sensibility. He is just the way he is and the way he says things just makes me laugh so hard. And we knew he’d be perfect for it. And it was like, once he showed up and started doing his thing, I was like, I can’t believe we got away with this.”

The series ends — perhaps surprisingly — on a cliffhanger where Persaud’s character, Ichabod Crane, opens his door and seems shocked to see someone whose identity we don’t get. “I like things that leave us some question marks,” he explained of the decision to leave the finale open-ended. “And I don’t always necessarily think that’s like, oh, great, there’s going to be a sequel to this movie. It’s more of just like, send people out thinking about the future and what other stories there could be and people can fill in the blanks.”

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Still, the abrupt ending begs the question: Could we possibly get more Headless stories in the future? While Persaud slyly shared that, yes, he does know the identity of the person on the other side of the door and “an idea of what that would mean for the characters and how that might inform a second season,” for now, he’s simply proud of the story that his company and his friends have put into the world.

“Everybody who is there really wanted to be there and really was invested in the project. And that’s something that we’re really proud of at Shipwrecked — creating a space where people are comfortable just coming and in doing their best work and it’s sort of like a little family on set. And that’s the reason why we get to do this.”

Headless: A Sleepy Hollow Story, All Episodes Streaming Now, Shipwrecked Comedy on YouTube