Shipwrecked Comedy Breathes New Life into a Literary Classic with the Premiere of Headless: A Sleepy Hollow Story

Shipwrecked Comedy, known for their historical, visually striking storytelling and their Streamy Award-nominated Edgar Allan Poe’s Murder Mystery Dinner Party, turns the Washington Irving classic short story “The Legend of Sleepy Hollow” on its head with the premiere of Headless: A Sleepy Hollow Story. 

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 on the literary classic follows awkward science teacher Ichabod Crane (Sean Persaud) as he finds himself roommates with the legendary Headless Horseman and must embark on a journey to find his new friend’s old head while discovering himself along the way.

“With Headless, we wanted to find a way to keep the story fresh and interesting with each episode while staying true to the original mysterious nature of the titular character. We wanted to answer the question of ‘who is the Horseman and what is he like when he’s not chopping off heads?’” said star and creator Sean Persaud. “We decided to explore this with the storytelling device of the Horseman trying on different heads in each episode. This allows us and the audience to meet numerous versions of the Horseman, each played by a different notable and talented guest actor providing their own take on the character.”

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.

The first installment of the 10-episode series is available now on Shipwrecked Comedy’s YouTube channel (youtube.com/shipwreckedcomedy), with new episodes airing every Monday, culminating with the finale on Halloween answering the show’s penultimate question of the Horseman’s identity.

Shipwrecked Comedy is a production company committed to creating dynamic, funny, and intelligent content for digital spaces and beyond. Founded during the summer of 2013 by sibling writing partners and actors Sean and Sinéad Persaud and joined later by actress/producers Mary Kate Wiles and Sarah Grace Hart, Shipwrecked has attracted a very diverse, active and loyal audience by presenting stories in a way that is exciting and different from the usual digital fare. From the Clue-inspired murder mystery Edgar Allan Poe’s Murder Mystery Dinner Party, to their film noir short The Case of the Gilded Lily, to their sketch that imagines the March sisters into a devilish coven, Little VVomen, Shipwrecked has amassed over 5.5 million views, raised over $400K through crowdfunding, and solidified their place as the internet’s home for smart, historical, visually striking storytelling.