“Deep in the forest, where ghouls haunt and wallow / There’s a town by the name of Sleepy Hollow” – Headless: A Sleepy Hollow Story

On August 29th, 2022, the legend began again, with Headless: A Sleepy Hollow Story premiering on Shipwrecked Comedy’s YouTube channel. The series is written by siblings Sean and Sinéad Persaud, who also star as Ichabod Crane and Matilda Bishop. Instead of following the traditional story of the Headless Horseman terrorizing the residents of Sleepy Hollow, the Persauds take the story in a new direction – What if Ichabod and the Horseman were roommates solving the mystery of the Horseman’s head?

Recently, I had the chance to talk with Sean and Sinéad about the series and what it has been like adapting the classic Washington Irving short story, The Legend of Sleepy Hollow, into a musical comedy on YouTube. We discussed their inspirations, being both writers and actors, and even favorite props!

*Spoiler Alert – There are spoilers for the series in this article, so please consider watching all ten episodes before reading this!*

Kat: So what inspired you to create Headless?

Sinéad: I have always been a huge fan of The Legend of Sleepy Hollow. A few years ago, Sean and I were talking about what our next project would be and we were toying with the idea of “What if Ichabod and the Headless Horseman were roommates?” We really love to take spooky, weird things and put a comedic twist on them, so that’s the route we went. It became a lot more complex and more of a mystery than we originally intended it to be! But that was our initial inspiration, making something quirky and funny out of something terrifying.

Sean: When we’re looking for a project to do, we’re going to be working on it for a long time and putting a lot of time, effort, and energy into it, so we want it to be something that we love. When we came up with this whole thing, there was something about it that just clicked like “Oh, yeah, this is worth it.”

Kat: What was the creative process going from the short story to the series?

Sinéad: Well, it was certainly different than any other process. We had an outline and we came up with the concept that the Headless Horseman is going to be many different people over the course of the show. We had a deadline that we certainly did not hit! It was like “January 2020, we’re gonna have a whole series written” – Certainly did not. But then we were like, “Okay, we’re gonna film in June. So we’ll get the Kickstarter video written and then we’ll spend all the time after the Kickstarter is done writing the series.” And then, of course, we didn’t because there was COVID and we never knew when we were going to shoot it. So the creative process got bogged down in not knowing when we were ever going to make this show. We wrote here and there for the next year and a half and lots of things changed. The script ballooned into 180 pages! As we started to zero in on a timeframe to shoot again, we scaled it back and were able to cut away the excess.

Sean: We wrote most of it over Zoom during the lockdown and it was a little disjointed – It took a long time. It was a little frustrating when we were editing and trying to streamline everything but we did it!

Kat: When you were writing the show, did you have specific people in mind for the characters? And once they were cast, were the actors able to help develop their own characters?

Sean: Yeah, for a lot of the characters, we had very specific people in mind. Like Jon [Cozart], like Gabe [Greenspan], and us, obviously. I think it’s always been really helpful for us to do that. We know what people’s strengths are, so we get to write towards those strengths. In that way, they help develop the character. But also, once we’re on set with Joe William Stribling, our director, it’s very much an environment where people come in and do their thing. There’s a reason we asked you because of what you bring to it. 

Kat: How much research went into the show and keeping to the storyline of the original?

Sinéad: A lot! We have a lot of characters who are named after other Washington Irving characters and stories. Matilda, my character, is named after Washington Irving’s wife, we’ve got Judith Gardiner, Rip Van Winkle, Geoffrey Crayon, Diedrich Knickerbocker . . . Almost everyone has some vague tie-in to Washington Irving. We were like, “This would be fun if this can tie in here!” And then sometimes we’re just like, “That’s just a fun name!” With the magic, I would say a cursory level of research was done there. In terms of the history, we did really dive into what the history was, like the founding of these towns and the people who were involved. We had a much larger idea of what the show was going to be and we had some other characters from history who were going to show up here and there.

Sean: And we obviously read the short story a bunch of times. The first episode basically follows the plot of the short story. But the short story’s plot is pretty slight and we felt like it was fine to just jump off from there, so we did! We had watched the Tim Burton movie, then we went and skimmed the Wikipedia page for the Fox TV show because we had never seen it and we just wanted to make sure that we weren’t overlapping on any of our ideas, and we were fine. 

Kat: What is it like creating a show like this specifically for an online audience, knowing it’s not on television or on the stage?

Sinéad: It’s strange! I definitely think that it is more suited for a television audience. I think when people go to YouTube, they’re not looking for something like this. They’re like, “What? Why is it twenty minutes long and on YouTube? It’s not a beauty video?” 

Sean and Kat: [Laughs]

Sinéad: That’s maybe not one of our strengths, catering to an online audience. We definitely want to be more in the traditional sphere and this is just how we’ve been able to get our content out in the past. But we do try to keep in mind specific like having a great thumbnail, with popping faces and color, and having cliffhangers – That way people will hopefully come back for more! 

Sean: It is really nice to have instant reactions – We’d have premieres every week, live chats, and comments. That’s really nice. I’ve never had a show on TV, but I don’t think it’s something that that exists there! And when we make the jump into the next platform, that’s something I’ll miss.

We had a big screening of the entire show at the place where we filmed, the Heritage Square Museum, and it was really great to see it with an audience and see what they reacted to.

Kat: So when you created Headless, you knew you were going to be playing your characters from the beginning. Do you feel like you put a lot of your quirks and personality into the roles?

Sinéad: I like to think that when we write things, we don’t think of it as ourselves playing them. Like, if I got sick, we could cast someone else and it would be great. That being said, I feel like now that I see it, I’m like, these characters are very much like alternate versions of me and Sean. 

Sean: For me, there’s the writer version of me and then there’s also the actor version. As an actor, I have a bag of tricks that I don’t want to just keep resorting to. So I feel like I was trying to write in a way that would be different and a little challenging, but then I’d get on set and start embellishing and improving in ways that I think I always do because I get on set and panic as an actor. I’ll do whatever I can to make people laugh. I’ll look like an idiot. I’ll just do my usual shtick. 

Kat: You mentioned improv – Was that encouraged? Or were you trying to keep to the script?

Sinéad: It’s hard when you have such a crazy time limit, but we do always manage to get some improv in there, especially on final lines and such. We have a couple actors who will come up to us and be like, “Is it okay, if I say it like this this time?” And we’re like, “Yeah, do whatever!” It’s probably going to be better! [Laughs]

Sean: And you have the Tin Can Brothers who will improvise – Every single take is different, which is really fun. It’s really fun when you’re editing, but then you also have to pick one! A lot of the improv happens on the edges of the scenes. Especially with this, there are a lot of very specific things, a lot of information that has to be expressed. But it’s nice that we, the writers, are there so we go “Oh, yeah, you can’t change that.”

Sinéad: We need you to say that date very clearly.

Kat: You mentioned how the story changed over time because you had some breaks during the writing process. Had you always had the ending established?

Sinéad: Yeah, pretty soon into the writing process, we had figured out what was going to happen, who it was, and the whole “Kat is evil” thing.

Sean: So our problem is we come up with our premise and beginning and then we come up with an ending, which I think is the hardest part. And then the middle section is often like, “Well, how do we get from there to there?” So yeah, the ending was always done. Some minor things changed, but the the identity of the Horseman was figured out very early on, and the idea that

Kat is dead and manipulating Ichabod . . .  

Kat: Have you been able to see how your writing and acting has changed since Edgar Allan Poe’s Murder Mystery?

Sinéad: I want to say yes, but then I don’t have any specifics as to why! [Laughs] And then I just start to think, “Maybe it’s our camera crew that’s gotten better . . .”

Everyone: [Laughs]

Sean: I think that it’s gotten better. To echo Sinéad, I don’t really know how. This is really the only thing like this we’ve written since Poe Party and it is bigger and more intricate. I think the emotional stakes are more interesting and nuanced and there’s a lot more to unpack. It’s weirder!

And then we’ve written a lot of other stuff in between, pilots and stuff for ourselves. We co-wrote on a video game earlier this year. I will say that I have noticed that Sinéad has grown a lot as a writer in the last six years. 

Sinéad: Thanks!

Sean: You’re welcome! I almost didn’t say it because I was like, “I don’t want this to sound like an insult to six years ago Sinéad . . .”

Sinéad: [Laughs] She was dumb! She was like “Hey, what if all these authors who didn’t live at the same time . . .” I do think we are both a lot more confident in our skills. If someone had hired us right off, six years ago, we would have obviously taken it, but now I would be like, “Yeah! We deserve to be here!”

Kat: And now some rapid-fire questions! Favorite character from Headless?

Sinéad: Oh, I’m gonna go with the bard, Diedrich Knickerbocker. I love him.

Sean: I’m gonna go with Brom!

Kat: Favorite line from the series?

Sinéad: I’m gonna say that I think I wrote it, but I just love it! And the way Gabe says it is so funny. He comes in and I’m like, “Did you get the ginger root like I asked for?” “Ginger root? I thought you said toilet paper!” He just nails it and it’s the stupidest thing. That’s the first one that came to mind.

Sean: It might be another Gabe line which is, “Oh, he’s not dead. He’s on a cruise,” about his dad. Or when Devlyn says “Remember to use promo code ‘Devlyn’ for 10% off” and no one knows what it’s for.

Kat: Character you’d want to play if you didn’t play your character?

Sinéad: I very very much considered just playing Verilla. I would’ve had time onset to just chill, but I’m glad I didn’t because she’s amazing.

Sean: Maybe Polly Tahoe? He was my baby.

Kat: Favorite prop from the show?

Sean: Part of this series used to take place in a bowling alley, which was a nod to Rip Van Winkle. So way back in 2020, I got a see-through glass bowling ball. I was told not to buy it by Sinéad and Mary Kate but I bought it anyways because I was like, “We’re gonna use this!” I wrote it into the script and then we changed everything and never used it.  

Sinéad: I took from set this really cool black rotary phone that I just keep on my desk, so maybe it’s that! 

Kat: And finally, one word you would use to describe Headless?

Sinéad: Whimsical! 

Sean: That’s what I was gonna say! 

Sinéad: Now you have to say something else! 

Sean: Mischievous! 

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Shipwrecked’s next project The Case of the Greater Gatbsy, a sequel to The Case of the Gilded Lily, will be coming out next year!

Thank you to Sean and Sinéad Persaud for the wonderful interview and to Mary Kate Wiles for her assistance!