If you think you know the tale of the Headless Horseman, think again. Because you’ve never seen a Headless Horseman tale quite like the one that Shipwrecked Comedy has created.
Headless, premiering today, is the latest series from the production company who, in their words, are “committed to creating dynamic, funny, and intelligent content for the digital spaces and beyond.” Founded in the summer of 2013 by Sean Persaud (Mank, Gaslit) and his twin sister, Sinead (The Only Podcast Left – Daybreak), the group has produced numerous shows that marry both history and literature in humorous, engaging ways, ranging from a Clue-inspired murder mystery dinner party to a noir film.
Its newest offering is a twist on the famous Legend of Sleepy Hollow story that has enthralled and haunted audiences for decades, starring both Persaud siblings as well as Mary Kate Wiles (The Lizzie Bennet Diaries, The Fairly Oddparents: Fairly Odder), Joanna Sotomura (Barry), Curt Mega (Glee), Krystina Arielle (Star Wars: The High Republic), Parvesh Cheena (Mythic Quest, Shining Vale), Kim Whalen (Being Mary Jane), and John Rubinstein (Being the Ricardos, Chilling Adventures of Sabrina).
Sean tells TV Insider that Headless was primarily the brainchild of his sister, who “came up with this idea as a young fanfic writer.”
“She wrote fanfic for the Tim Burton movie where Ichabod and the Headless Horseman were roommates,” he shares. According to Sean, Sinead pitched the idea to her brother a few years ago during Comic-Con while they were rehearsing for a Brooklyn Nine-Nine activation, and he was immediately on board with the concept of “what if Ichabod and the Headless Horseman were in an Odd Couple-like sitcom?”
The 10-episode modernized series explores exactly that as Ichabod (Persaud), an awkward science teacher, finds himself with a roommate in the form of the Headless Horseman — and on a mission to his new friend find his old head. To make things even more fun, each head that the Horseman tries on is portrayed by a different guest star — a star-studded roster of actors that includes names like 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), Julia Cho (The Lizzie Bennett Diaries), Audrey Grace Marshall (The Fairly Odd Parents: Fairly Odder, The Flight Attendant), and Ryan Garcia.
For Mercer, who spends most of his time spinning tales as the Dungeon Master of the hit web series sensation Critical Role, taking a few moments out of his (very) busy schedule to play a swashbuckling, bumbling, centuries-old pirate named Captain Gravy Davy Crowbones was a no brainer. “There’s a certain point where you get busy, and you have to realize part of self-care is allowing yourself the space to do things for yourself,” he told TVInsider. “As a performer, it’s rare that you get the chance to really just, you know, jump in both feet into a character of this level of ridiculousness. And so, it’s kind of finding the line of him being this overt caricature of the classic, cinematic pirate that we’re used to seeing, especially in more modern times, but still finding that sort of man of time, interpersonal comedy that you don’t get to see in a lot of pirate based media.”
Finding the specific nuances to pull out of one of literature’s greatest characters was a similar journey for Persaud. “He’s depicted as very greedy, and, you know, he just takes off but then he just runs away,” he said, adding that in the short story the character is less than likable. “I wanted to steer away from that, but I wanted to make him sort of inquisitive, a little easily spooked…the dichotomy of him working with the Headless Horseman is like the central conflict of the show.”
While Headless is only 10 episodes, there’s potential for more stories down the line. “We have multiple documents of discarded ideas for this,” Persaud admits. “There were a bunch of characters that we wanted to bring in to help them solve this mystery. We also wanted to do just a standalone episode of like, what’s it like to be brought back to life? And for a day? What are the different types of reactions to that? Are there people who wouldn’t like it? Are there people who would be like, I’m not part of this, I need to go take care of some unfinished business? We had so many fun ideas and that’s the hard thing.”
For now, fans should enjoy the ride — an unexpected, hilarious ride.
“The cliffhanger from Episode 3 was like the big thing that we were like, ‘we got to do this.’ We didn’t know how it would play out. And then as we were writing, we figured out something that I think was very satisfying to us and very surprising,” Persaud teases. “I hope that people are excited to see where that goes.”
Watch an exclusive sneak peek below:
Headless: A Sleepy Hollow Story, New Episodes Mondays Through Halloween, Shipwrecked Comedy on YouTube