“Headless: A Sleepy Hollow Story” Review by Ruth Kennedy
“Vaguely Historical. Loosely Literary. Stupidly Smart.” This is the tagline for Shipwrecked Comedy, a YouTube-based production company that has been creating sharp, funny, free-to-watch video content for literature lovers everywhere since 2013. Founded by siblings and writing duo Sean and Sinéad Persaud, they, along with their fellow producers Mary Kate Wiles and Sarah Grace Hart, have crafted multiple incredible tales filled with humor, mystery, and references to classic literature and film.
I first found Shipwrecked in the summer of 2020, when I was seeking solace from the pandemic by going down the rabbithole of the world of YouTube web series. A personal love of Edgar Allen Poe and the inclusion of actors from familiar YouTube channels drew me to their 2017 series Edgar Allen Poe’s Murder Mystery Dinner Party. It is a ten-part story where various authors including the likes of Oscar Wilde, Earnest Hemmingway, Charlotte Bronte, and a host of others have to solve a murder mystery as they are picked off one by one. While I expected a few good laughs, what I found blew me away. The series features a quick-witted script, hilarious acting, and, most appealing, a love for literature that I can relate to.
Some other notable Shipwrecked projects include 2015’s Kissing in the Rain, the story of two sets of actors navigating various romantic movie scenes, 2019’s The Case of the Gilded Lily, a comedic spoof on noir detective films, and 2020’s Little VVomen, a haunting reimagining of Louisa May Alcott’s classic novel.
In 2022, Shipwrecked announced a new project, one which would be their biggest since Poe Party in 2017. Returning to their founders’ New England roots, Shipwrecked adapted Washington Irving’s classic 1820 American ghost tale The Legend of Sleepy Hollow in the modern day with a ten-part web series, Headless: A Sleepy Hollow Story.
Clocking in at over two and a half hours(not counting promotional and supplementary materials), Headless represents a massive undertaking for the small independent production company. Over a year of pre-production, filming, editing, and promotion went into the series, and in my opinion, every second was well-spent.
Headless follows the story of middle school science teacher Ichabod Crane(played by Sean Persuad) as he arrives in Sleepy Hollow to start a new chapter of his life. When he goes in search of a roommate, he gets more than he bargained for when he encounters the legendary Headless Horseman. The Horseman promises to help Ichabod pay his rent if he helps him find his original head. The duo go on a series of adventures as they search for the Horseman’s missing head, encountering mystery, intrigue, and hilarity along the way.
A main premise of this series is that every time a new skull is put on the Horseman, he takes on the identity of that skull. This ingenious idea allowed the series to feature a rotating list of characters as the Horseman, expanding the cast and giving Shipwrecked the opportunity to bring in guest stars from many corners of the entertainment industry. The worlds of table-top role playing games, stand-up comedy, Hollywood acting, and YouTube-based theatre all poke their heads in to contribute to the delightful madness that is the search for the Horseman’s head.
Aside from the Horseman’s temporary heads, the cast includes a crew of oddballs to help Ichabod in his quest. Readers of Irving’s classic story will recognize Ichabod’s love interest Kat van Tassel (played by Shipwrecked producer Mary Kate Wiles) and village strongman Abraham “Brom Bones” Van Brunt(played by Shipwrecked collaborator Gabe Greenspan.) Different members of Ichabod’s crew reference other aspects of New England folklore, such as witch Matilda Bishop(played by Sinéad Persaud) and woman-in-white-esque ghost Verla Wolfson(played by tabletop gaming YouTuber Ginny Di.)
Sean and Sinéad Persuad’s writing in Headless is as smart and intriguing as I have come to expect from Shipwrecked, keeping me hooked until the very end.
Shipwrecked was also able to garner enough support from its fan base to fund a companion series for Headless, the seven-part Unsolved Babesteries. This cheesy-on-purpose series features the characters of Brom’s Babes, a trio of wholesome frat-boy-parody comedic lackeys for Brom Bones. Portrayed by YouTube web series and theatre producers the Tin Can Brothers, the Babes use their series to expand on Headless’ main storyline in their own dopey way, giving the audience extra time with the tertiary and guest cast of Headless while letting the main storyline continue uninterrupted.
Sean and Sinéad Persuad’s writing in Headless is as smart and intriguing as I have come to expect from Shipwrecked, keeping me hooked until the very end. The mystery of the Horseman’s true identity weaves throughout the series, and every episode adds new pieces to the ever-expanding puzzle. While the script is full of comedic moments, it is also deliberate, with characters and lines rarely added for the sake of fluff. The series is also rich with detail in both dialogue and set decoration, giving attentive viewers many things to pick up on and the whole series a high rewatch value.
Under the direction of frequent Shipwrecked collaborator William J. Stribling, Headless is not only fun to watch, it is beautiful to look at. The series was filmed at the Heritage Square Museum in Los Angeles, which boasts eight historic homes from the 1800s. The crew of Headless, led by Stribling and with design by production designer Alexander Whittenberg, transformed this location into a living, breathing Sleepy Hollow, bringing New England flair and beauty to the West Coast.
The costuming of the show is also exquisite. The Headless Horseman’s costume is completely practical, designed so that the character looms over others around him while the actor(Tom DeTrinis, a frequent actor in Shipwrecked projects) can interact and build a rapport with the other characters. The variety of heads put on the Horseman also allowed costume designer Morgan Gannes to explore different time periods and implement colorful costumes in the modern setting.
It would be remiss to not mention the music of Headless, which elevates this series to a higher level. In the story, the characters are often followed around by the town’s bard, Diedrich Knickerbocker (played by musical YouTuber Jon Cozart.) Knickerbocker adds an element of storybook whimsy to the story, popping up to offer catchy bits of narration. The series is also accompanied by a beautiful score from composer Dylan Glatthorn, whose memorable theme song and haunting melodies bring Sleepy Hollow to life.
I could go on and on about all the things I love about Headless–the way certain characters develop over the series, a hundred tiny details from Irving’s writings sprinkled in, the crazy amount of talent the Shipwrecked team was able to pull together to make this show happen. Once I convince someone in my life to watch the series, I will certainly take my opportunity to ramble. For now, I will pause to leave this review spoiler-free, so that interested viewers can experience the joy of a storyline full of twists and turns.
Headless became a welcome part of my routine in the past couple of months. As life whirled by in its predictably chaotic way, I always knew I could turn on Headless and be met with excellent writing, love for a classic source material, and a production value that shows a remarkable care for the craft of visual storytelling.
Premiering on August 29, 2022 and posting weekly episodes until its finale on Halloween, Headless became a welcome part of my routine in the past couple of months. As life whirled by in its predictably chaotic way, I always knew I could turn on Headless and be met with excellent writing, love for a classic source material, and a production value that shows a remarkable care for the craft of visual storytelling.For anyone interested in smart, literature based storytelling and incredible film technique, I could not recommend Shipwrecked Comedy enough. Headless is just one example in their ever-growing catalog of incredible work. In everything that they produce, the Shipwrecked team shows a deep appreciation and care for the stories they are adapting, leaving no stone unturned as they use beloved figures and literature as the building blocks of their innovative projects.