Shipwrecked Comedy’s New “Headless: A Sleepy Hollow Story” Premieres This Month

Shipwrecked Comedy's Headless: A Sleepy Hollow Story Official Promotional Poster
Headless: A Sleepy Hollow Story Promotional Poster

( ENSPIRE Entertainment ) Original Web Series Headless: A Sleepy Hollow Story Funded by More than $200,000 in Kickstarter Donations

ENSPIRE Contributor: Abigail Elcock

The trailer for Shipwrecked Comedy’s latest web series Headless: A Sleepy Hollow Story has officially dropped! Shipwrecked Comedy was originally founded in 2013 by writing partners, actors, and twins Sinéad and Sean Persaud. The production company is known for merging the literary and historical with dry humor and comedy. Its previous production Edgar Allan Poe’s Murder Mystery Dinner Party was viewed over 2 million times on YouTube and nominated for multiple Streamy Awards in 2017. Headless: A Sleepy Hollow Story is sure to be another Shipwrecked Comedy success story.

Headless tells the story of Ichabod Crane, a science teacher who just moved into the odd town of Sleepy Hollow. When he moves in, he realizes he must become roommates with the headless horseman. Ichabod does not like the idea of a roommate without a head, so the two embark to discover the true head of the horseman. In each episode, the horseman takes on a new head and personality, and the two meet residents of the town who might be able to help.

Ichabod Crane and the Headless Horseman are Roommates in Shipwrecked Comedy's Headless: A Sleepy Hollow Story
Ichabod Crane (Sean Persaud) and his new roommate the Headless Horseman

The concept behind Headless actually started out as fanfiction. Sinéad Persaud loved Washington Irving’s classic and wrote about it often as a young teen. “I was always pretty into Sleepy Hollow, probably because of the Tim Burton version,” Sinéad reminisced. “I thought it was really funny to have the Headless Horseman be a comedic character.” 

In 2019, when she and Sean were brainstorming Shipwrecked Comedy’s next big production, they dived more into that idea together. Sean talked about the experience saying, “It started out a lot simpler… as a series of vignettes, sort of like a sitcom—what if Ichabod and the Headless Horsemen were roommates?… And now it’s turned into this huge town [with] complex interweaving mysteries.” Before the two knew it, they had a new project they knew their fans would love.

Exclusive Abigail Larson poster of Headless from Kickstarter.

Shipwrecked Comedy's Headless: A Sleepy Hollow Story
Exclusive Abigail Larson poster of Headless from Kickstarter

Shipwrecked Comedy has a unique connection with its audience. A large part of this is thanks to Kickstarter. Through Kickstarter, a global crowdfunding program, anyone can bring their creative projects to life. Shipwrecked Comedy has historically used Kickstarter to fund its productions. Kickstarter also gives backers behind-the-scenes information about the project, exclusive merchandise, rewards, and more! Even before a project is in production, Shipwrecked Comedy fans are already looking forward to the final product.

With Headless, Shipwrecked created their most ambitious Kickstarter yet, setting a crowdfunding goal of $150,000. People were further incentivized to donate because cast members and Sleepy Hollow characters were revealed after every $7,500 mark. Not only did Headless meet its crowdfunding goal, but it far exceeded it. When the Kickstarter closed, Shipwrecked had raised $201,947 with the help of 2,386 backers. To say Headless is highly anticipated is an understatement.

Shipwrecked Comedy's Headless: A Sleepy Hollow Story on Kickstarter
Shipwrecked Comedy funded Headless: A Sleepy Hollow Story on Kickstarter

In less than three weeks, Shipwrecked Comedy will share Headless: A Sleepy Hollow Story with the world. Sean Persaud expresses pride in all their hard work saying, “Headless represents a very clear leveling up of Shipwrecked and all the things we do…This feels like a proper follow-up to Poe Party because it’s a big undertaking…but it also feels like very new and very fresh and very fun.” Sinéad Persaud chimed in, “We just really try to push the boundaries of what you can do on the internet with a ridiculously small amount of money, and maybe we shouldn’t be doing that, but we’re going to! That’s what we do here at Shipwrecked.”

Subscribe to Shipwrecked Comedy’s YouTube channel to be one of the first to watch Headless: A Sleepy Hollow Story. The first of ten episodes will premiere on YouTube on Monday, August 29. Subsequent episodes will be released weekly. For all the latest on the series, you can visit Shipwrecked Comedy’s official website or follow Shipwrecked on Facebook, Instagram, Twitter, or Tumblr.

Related Articles: Prince Chijioke and “Never Say Never”, Dungeons & Dragons: Honor Among Thieves Trailer Trending Worldwide, Black Women in Comedy Laff Fest Celebrates Talented Black Women