A Sleepy Hollow Review

Even for the most unfamiliar viewer with Washington Irving’s The Legend of Sleepy Hollow, the premise of this webseries seems simple. A young man named Ichabod Crane movesto a little town called Sleepy Hollow, uncovering mysteries along the way. Produced by Shipwrecked Comedy made of and starring Sean Persaud (Ichabod Crane), Sinead Persaud (Matilda Bishop), Mary Kate Wiles (Kat Van Tassel), and Sarah Grace Hart (Lucretia Lazenby), the series was published for free on YouTube, with the first episode posted on August 29, 2022. Written by sibling duo Sean and Sinead Persaud and directed by Willian J. Stribling, Headless: A Sleepy Hollow Story is a fresh look at the world of Sleepy Hollow through a modern lens, exploring themes of friendship and family as Ichabod and the audience learns that not everything is as it seems.

When Ichabod Crane moves to Sleepy Hollow as the new middle school science teacher, he meets an array of new faces, including Kat Van Tassel, Matilda Bishop, Brom Bones (played by Gabe Greenspan), and Kat’s amicable father and town mayer, Baltus Van Tassel (played by John Rubinstein). When his landlord hikes up his rent, Ichabod is forced to find a roommate in a pinch. But when the town’s legendary Headless Horseman shows up at his door, Ichabod finds that there might be more to this town than he knew. Little does he know, he’s more connected to this town than he thinks.

The cast of Headless includes a wide array of larger than life characters, who are all grounded beautifully by their respective actors. Standouts include Gabe Greenspan as Brom Bones, the resident P.E. teacher with the same jockish airheadedness as his usual character trope, but with a refreshing earnestness, loyalty, and desire for growth, as well as Sinead Persaud as Matilda Bishop, the goth-girl drugstore worker with a hidden warmth. Mary Kate Wiles also shines as the level-headed cool girl Kat Van Tassel, whose energy brings a much needed shift to a big twist near the end. This is a cast of people who have worked together many times before, and their camaraderie and rapport shows in the understated moments of connection between their characters, whether heartfelt or humorous.

The production on this series, particularly for something that was independently funded, is surprising, with beautiful sets and locations and some stunning cinematography. The camerawork shines especially in “Episode 8: A Heist at the Hotel”, which includes lots of quick edits as well as one long shot that switches between several characters in rapid succession. The lighting is also consistent, as the crew makes use of natural daylight when appropriate and works to use stark lighting in night shots for more suspenseful moments. The finale includes some particularly striking lighting, with a stained glass window shining onto a dark wooden floorboard. The one thing that leaves a bit to be desired is some of the post-production effects, as they can have a very computer-generated feel in some shots. However, this is almost completely made up for by the practical effects, including with the Headless Horseman, which featured an actor in a costume that was built around him to simulate shoulders and a neck.

Headless has also been praised for its music, with the instrumental theme and score composed by Dylan Glatthorn, and Diedrich Knickerbocker, the town’s local bard, singing songs written by his very same actor, Jon Cozart. Though not a musical, the show gains a lot from keeping Knickerbocker in this adaption, primarily in its comedic timing; however, his presence elevates an especially dramatic moment near the end, where the fate of one of the major characters is finally revealed.

While Headless has a fairly small viewership, with the first episode only recently having reached 1 million views, it has received high praise from its fans, particularly in the show’s writing and acting. Currently, the production team has been working hard to promote this project, especially with hopes of a second season being produced on the horizon.

This is why I have to recommend that as many people as possible watch this show. Its more serious themes are tempered by witty humour, with characters like Brom Bones and Matilda Bishop unforgettable in this adaption. It features so many skilled actors both in its main and guest cast, and well-earned twists, with heartwarming moments of growth along the way. Headless is a new step forward in the land of digital media, and deserves a larger platform to fully shine.