Today, Shipwrecked Comedy premieres Headless: A Sleepy Hollow Story, a new spin on the Washington Irving classic! Known for their visually stunning storytelling and Streamy Award-nominated Edgar Allan Poe’s Murder Mystery Dinner Party, Shipwrecked has a knack for taking classic tales and turning them right on their head!

Starring Sean Persaud (Mank, Gaslit), Mary Kate Wiles (The Lizzie Bennet Diaries, The Fairly Oddparents: Fairly Odder), Sinead Persaud (The Only Podcast Left – Daybreak), Joanna Sotomura (Barry), Curt Mega (Glee), Krystina Arielle (Star Wars: The High Republic), Parvesh Cheena (Mythic Quest, Shining Vale), Kim Whalen (Being Mary Jane), John Rubinstein (Being the Ricardos, Chilling Adventures of Sabrina) and more!

This ten episode modernized, comedic update to the classic tale follows around our protagonist, award science teacher Ichabod Crane, played by Sean Persaud, as he finds himself roommates with the Headless Horseman! Crane embarks on a journey to find his new friend’s old head, while going on a journey of self-discovery along the way!

What To Expect from Headless: A Sleepy Hollow Story

We had the chance to speak with two of the stars of Headless: A Sleepy Hollow Story, Mary Kate Wiles and Sean Persaud about what audiences have to look forward to.

This is such a unique spin on a classic tale – what are you most excited for the audience to see?

• Sean Persaud: The answer to this changes every day. I’m really proud of the story we’ve built out from the original short story, and I’m excited to see people’s reactions as they follow along. But my favorite part of writing was taking a break from the big picture stuff and fleshing out the silly fringes of the town of Sleepy Hollow. That said, we have some very funny side characters and an incredible cast. There are some throwaway jokes in this show that still make me laugh even after watching them 100 times, and I can’t wait to see if any of that resonates with viewers as well.
• Mary Kate Wiles: Oh man, it’s hard to choose. We’re really proud of this show. But some of the identities that the Horseman takes on are particularly delightful and they are played SO well by their respective actors – everyone’s giving 150%. I’m excited to see who the audience’s favorite Horseman will be. I think it will be different for everyone because they’re just all so good.

How did Headless come to be?  What was the thought process behind taking a story everybody knows and making it your own?

• Sean Persaud: My sister and co-writer Sinead actually had the original idea for this when she was little. She loved the Tim Burton Sleepy Hollow movie and wrote fanfic about it where Ichabod and the Headless Horseman are roommates, which is just a great pitch that paints an instant and vivid picture. A couple years ago, we were brainstorming about possible new projects and she brought that up, and I suggested making it a little bigger than a sitcom about odd couple roommates. We instantly were intrigued by this whole idea – taking the nebbishy Ichabod and this legendary ghost and throwing them together as strange bedfellows with the narrative spine and the stakes of trying to find the Horseman’s head, it was a new and exciting story, and something we had never seen from various adaptations of this. The original short story is fairly slight, so it was fun taking pieces of it and creating something new: a longform show that is whimsical, mysterious, and – I hope – kind of sweet.
• Mary Kate Wiles: I can’t really speak to this question because I’m not one of the writers, but the way that Sean and Sinéad take well-known stories or figures from history and put a new, different, inventive spin on them is absolutely one of the things that drew me to their writing in the first place. It’s so uniquely them and so unlike anything I see anyone else doing. It’s not just, “how can we tell ‘The Legend of Sleepy Hollow’ in a new way?” but “How do we tell the ‘Legend of Sleepy Hollow’ in a new way while also working in different Washington Irving works and nods to his other stories while at the same time making it something we would want to watch?” There’s always so much for audiences to dig into in a Shipwrecked show.

What are you hoping the audience takes away from watching Headless? 

• Sean Persaud: I think there are some nice messages about friendship and found family and trying to find yourself. Ultimately, I hope people are entertained and can, for a little while, tune out the existential dread hanging over everything. Is that just me? I also think our fandom has really connected through our storytelling, especially the longform week to week stuff we’ve done, and I hope that more people are able to find our fandom – it’s a really nice place!
• Mary Kate Wiles: I just hope they have a great time. We love to tell stories over a period of weeks – we’re really drawn to mysteries and doling out details episode by episode, drawing audiences in. We’re so looking forward to the experience of that, since the last time we did a multi-episode series was in 2016 with Edgar Allan Poe’s Murder Mystery Dinner Party. I hope people will be eagerly awaiting each new episode release.

Ichabod Crane is an iconic character – how did you prepare for the role and give your own twist?

• Sean Persaud: I did struggle with this – the Ichabod of the short story is not super likable, so that gave me and Sinead license to change things up. There are some fundamental things about the character – he’s new in town, he’s a teacher, he’s easily spooked. We built it out from there, while thinking about how his characteristics would serve the story and vice versa – as well as how he would interact differently with people in town. I wanted to make him inquisitive and an unabashed nerd – he’s awkward and he’s super into science and kind of a dork, but he’s pretty self aware and unbothered by it. There’s a delight and confidence to him, even though he’s always nervously reacting to the weird stuff happening around him. In that way, he knows who he is, but in other ways, he’s lost, and hopefully he’s able to find his way.

Without spoiling too much; can you tell us a little bit about your character and the role she plays in the series?

• Mary Kate Wiles: Yeah! I play Katrina Van Tassel – Kat, for short – and she’s one of the original characters from the short story, although she’s basically just a sweet ingenue type love interest for Ichabod in Irving’s version. Sean and Sinead have given me a lot of fun stuff to play with in their version of Kat. She’s the mayor’s daughter, she’s grown up in this town, but there’s a lot more that she yearns for. She’s sharp and subdued, and there’s a lot going on for her under the surface. She was a very fun challenge for me.

Each episode of the series is centered on the Horseman magically trying on a different head provided by a star-studded roster of guest actors in the hopes that this new persona will help our intrepid gang of townsfolk figure out the mystery of the Horseman’s true identity. Guest stars include Matthew Mercer (Critical Role, Attack on Titan), Jimmy Wong (Mulan, The Command Zone), Lee Newton (SourceFed), Lauren Lopez (Team StarKid), Dan Mintz (Bob’s Burgers) and Ryan Garcia (Big Nate) all providing their own take on the classic character, with Audrey Grace Marshall (The Fairly Oddparents: Fairly Odder, The Flight Attendant) and Julia Cho (The Lizzie Bennet Diaries) rounding out the guest star cast in as of yet announced supporting roles. Additionally, Shipwrecked Comedy is bringing in two more unannounced guest stars to be revealed around the show’s finale that will delight fans of horror, comedy, fandom and everything in between.

New episodes premiere every Monday on Shipwrecked Comedy’s YouTube channel culminating with the finale on Halloween and answering the show’s penultimate question: who is the Headless Horseman?

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