This interview was originally published 9/6/22.

Are you a fan of Sleepy Hollow, Headless Horseman and unique takes on old literature? Well, look no further than Shipwrecked Comedy‘s long slate of digital content. The production company recently kicked off their latest series, Headless: A Sleepy Hollow Story, and we instantly fell in love. Who wouldn’t want the Headless Horseman as a roommate in return for helping him figure out which head is his? We recently had the pleasure of chatting with Shipwrecked Comedy founders Sinéad Persaud, Sean Persaud and Mary Kate Wiles about the series, their favorite moments from filming and the epic cast that brought their story to life.

This interview has been edited for clarity and length.

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Shipwrecked Comedy

Icabod sitting across the table from the Headless Horseman.

Headless: A Sleepy Hollow Story

Julia Roth: First, I’d like to say that I absolutely loved the first episode of Headless: A Sleepy Hollow Story. I can’t wait to see where this story goes. So how did Shipwrecked Comedy start?

Sinéad Persaud: Thank you! I supposed it all started with Edgar Allan Poe. I’d written a sketch called Edgar Allan Poe Buys Girl Scout Cookies while in college, and I wanted my brother Sean (Persaud) to play Poe. Later, when I moved out to LA, we ended up making it, and it turned into a blog series that was very in Vogue at the time. Our blog started to get some traction on Tumblr, which led to us making a couple more series. So I brought on Mary Kate (Wiles) and my friend Sarah, a very talented costume person, to do some work. In 2016, we went on to do our big series, Edgar Allan Poe’s Murder Mystery Dinner Party, and it’s been a wild ride.

JR: Does this Edgar Allan Poe cookies skit still exist? And what kind of cookies did he buy?

Sinéad P: Why yes it is. And he is a Thin Mint and Savanah Smiles kind of guy.

Mary Kate Wiles: Watching this older skit and comparing it to what we have done recently really helps show how much we have grown as a company. It’s still a great skit and fun to watch, but it’s great to see that growth.

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Sean Persaud: I watch it and wish we could return to those minute skits.

JR: Thin Mints are a solid cookie choice. I am going to have to check this one out. Now, what is the connection to all of the literary stories?

Sinéad P: Mary Kate was an English major, and Sean and I were raised in Marblehead, Massachusetts, which is close to Salem, which is known for witchcraft and literature and Nathaniel Hawthorne. We grew up loving history and literature. We are huge nerds. So, you know, the kind of kids who escaped into books a lot. And I just brought that with me through my whole filmmaking career.

Sean P: It’s tough to make original content these days. It’s as if everything is sort of based on something based on an IP. We didn’t think about this, but it turns out that a lot of stuff is in the public domain and is the IP we want to work with.

MKW: This is also something people will recognize and have a touchstone for. You’re also able to play with the story and do things in a new way because it’s so old.

Sinéad P: We also love comedy and taking all of these old stories, concepts and people who were very serious and took themselves super seriously, bringing them into the modern world and putting them in silly situations.

JR: I love that you went with comedy. When I first saw the Headless: A Sleepy Hollow Story trailer, I thought it would be scary. And after watching the first episode, I knew this was going to be so much better. It’s refreshing to see a typically spooky story made into a comedy.

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MKW: That’s what we like to do! It’s fun to take something everybody knows and twist it a little bit. And hopefully, our audiences love this as much as they loved Edgar Allan Poe, where we had different authors getting murdered. We even heard about a few of our younger fans checking out books from HG Wells and George Elliot and discovering something they would never have gotten into.

Icabod standing next to the Headless Horseman and Brom Bones.

Headless: A Sleepy Hollow Story

JR: That’s always great to hear! Now, the first series was filmed pre-COVID, but the second one was done during everything. What were some struggles that you had to deal with?

MKW: We shot in February this past year for three and a half weeks. We had already pushed the shoot back a few times last year due to COVID and people’s other commitments, and finally, we were able to land on February. After the Omnicron surge in January, we were worried that we would have to push it back again, but we decided to take the gamble. We had an excellent COVID compliance officer who kept us safe and on track, and in the end, no one got sick. There was always the worry that if one of our main actors, like Sean, got sick, we would be utterly screwed. We didn’t have the backup money ready for that situation, so we were thankful we never had to work about it.

Sean P: We were definitely one of the lucky ones who were able to come out on the otherside of COVID and still able to put together a show. We owe a great deal of that to everyone who backed us on Kickstarter and continued to support us throughout the process.

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MKW: That made getting to film in February much more important. Plus, we got the chance to see all of our friends who we think should be super famous and on TV shows bring our story to life.

JR: It’s excellent to hear that you guys were able to survive COVID. So often, we hear about smaller indie companies that go under because they didn’t have the backing or money to push through the hard times. Now, you mentioned getting to see all the cast, and the list is packed with some incredible people. How did you guys convince them to come aboard? Bribe them with Girl Scout cookies?

Sinéad P: We paid them a little, of course. And we have fostered a great relationship with the people we have worked with previously and have proven that we are a really fun set to work on. We’re stressed out, but our director Joe Stribling is so much fun to work with, and it’s fun for everyone else.

Sean P: Oh yeah, definitely a fun, relaxed, joyful set on the outside. In our producer brains, it’s very stressed.

MWK: We invited people we worked with in the past, but we also invited new people too. Like Ginny Di and Matthew Mercer, who we’ve known for a long time and knew they would be great in the roles. Others like Krystina Arielle, whom we’ve never worked with before but know about through our friends, we thought would be good for the series. This is our first non-period piece, but it still has such a great vibe, and I feel like many of the people who worked with us were interested in bringing this story to life.

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JR: You mentioned that Headless: A Sleepy Hollow Story is your first modern piece. Was that something you planned, or did the story lend better to this time period?

Sinéad P: The idea was always going to be in the modern day. We never felt we had to do something modern but that this story would work better here. Plus, we kept thinking about all the money we would save on costumes until we decided to build an entire Headless Horseman costume from scratch.

Sean P: I think from the minute we thought about this concept, we knew it would just make sense to do it in the modern day. There is always the worry, too, that if we had done this as a period piece, it would have cost us so much more money.

MWK: We’ve also seen that this story also lends well to the present day; we have Fox’s Sleepy Hollow series that was modern and other Sleepy Hollow adaptations. It felt exciting to do something different and bring the characters into the modern space, especially with Bram and Katrina. It’s always interesting to try and get into their headspace, figure out how they would react to things, and expand on characters.

The production crew behind Headless: A Sleepy Hollow Story in front of the welcome to Sleepy Hollow sign.

Headless: A Sleepy Hollow Story

JR: What has been your favorite part about filming?

Sean P: Oh, that’s a fun question. I’m not sure I can share mine without spoiling anything, but Mary Kate got to do some action shots.

MKW: Oh yeah, that was cool. I would say shooting with the horse was amazing. So professional, and having a horse on set just felt like a huge step for us in terms of things we’ve never done before. It was one of the last things we shot, and it was just a magical experience. That scene appears in the first episode, but it was what capped off our shooting.

Sinéad P: The horse was a highlight for all of us, except that it was really, really cold that day. So the magical horse balances out the freezing temps.

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Sean P: So cold. For mine, I would say it would have to be that we wrote the entire role of Brom in mind for Gabe Greenspan. We were at the point that if he got COVID while filming or booking a big show, we weren’t sure what we were going to do. He did not disappoint on set and was such a fun guy to work with. No one could keep a straight face while he was on set, making every day a true delight.

MKW: That was what I was going to say, too, but I felt like it was a cop-out answer. But getting to see everyone on set and interact and bring this story to life was amazing. Having Jon Cozart narrate and sing for us was so freaking good.

JR: These are fantastic! So what’s next for Shipwrecked Comedy? Another season of Headless: A Sleepy Hollow Story, or do you have other projects in the works?

MKW: Well, this first season is very contained, but I won’t say that we haven’t thought about doing more seasons. But right now, we don’t want to get ahead of ourselves. We have another project on the way that we crowdfunded this summer. It is going to be an audio narrative with a film noir-type feel. It is based on a little movie we did called The Case of the Gilded Lily. This was always supposed to be a prequel to a bigger story, and now we get to tell it.

Sean P: The new project is called The Case of the Greater Gatsby and is about the death of F. Scott Fitzgerald. Officially, he died of a heart attack, but in our story, he is murdered. So two private detectives set out to find out who did it and why. It’s set in old Hollywood and a little wacky because we can’t do anything normal. It’s an original story of ours that integrates real events and people.

JR: This all sounds amazing! I will keep my fingers crossed that we see more from the Headless Horseman in the future, and I wish you guys luck!

Everyone: Thank you!

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