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The Headless Horseman Rides Again in the Legend of Sleepy Hollow at Mile Square Theatre

By Carolyn M. Brown, JerseyArts.com

originally published: 10/03/2024


The beloved tale of Ichabod Crane, the Headless Horseman, and the town of Sleepy Hollow is woven into the fabric of American folklore. A witty adaptation of Washington Irving’s timeless ghost story, "The Legend of Sleepy Hollow," comes to life on stage, October 3-20, 2024, at the Mile Square Theatre in Hoboken, New Jersey. The 80-minute show is full of twists, turns, and tee-hees, all told by one man, Shawn K. Jain, performing courtesy of the Actors’ Equity Association. Jain embodies a variety of characters using vocal and physical changes to transform seamlessly from one person to the next.

"The Legend of Sleepy Hollow" has been adapted several times, including the Disney animated movie in 1949 and the 1999 film by Tim Burton. The Mile Square Theatre’s version is a haunting and humorous one-man show written by John Minigan and directed by Devanand Janki. With a rich history in the performing arts and an impressive resume that includes Broadway hits like Miss Saigon and Cats, Janki is set to bring a fresh, diverse perspective to this classic story.

It was at the request of an actor in Boston that led Minigan to write the solo show two years ago. "His goal was to play Ichabod Crane. I only knew the story through other adaptations," says Minigan. "I was reading it for the first time, and I was struck by the story that Washington Irving, one of the first figures in American literature, created around the [tales] that we tell ourselves about ourselves. He was saying to us, be careful about disinformation and lies, because people will use them to get what they want from you," adds Minigan. "And I said, 'Wow, that feels really relevant in 2022,' which is when I wrote it."

Playwright John Minigan

While other adaptations have depicted the "Legend of Sleepy Hollow" as a tale of horror, "the original story is very funny," says Minigan. "So, my goal was to capture the humor of it and also the sort of spookiness that audiences will expect." He describes the solo performance as a tour de force for an actor to play more than 20 characters. "It takes a strong actor to carry the weight of all of that over the course of 80 minutes," he explains.

The play opens with Jain coming on stage as himself and then transforming into Washington Irving who arrives at a tavern and proceeds to tell a story that revolves around a hardened schoolteacher named Ichabod Crane in the town of Sleepy Hollow, part of the farming community of Tarrytown, New York, around the year 1790. Ichabod intends to court Katrina Van Tassel, the young daughter of an overbearing and wealthy farmer, in order to procure her family's riches for himself. In his attempt to woo Katrina, Ichabod crosses Abraham "Brom Bones" Van Brunt, a popular local suitor adored for his physical strength, prowess as a horseman, and penchant for playing pranks.




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A firm believer in the supernatural, Ichabod attends a harvest party at the Van Tassel home, where Brom spins a tale of the Headless Horseman, the ghost of a Hessian trooper decapitated by a cannonball during the Revolutionary War, who rises from his grave every night in search of his missing head. Heartbroken by Katrina rejecting his marriage proposal, Ichabod leaves the party, riding home on a borrowed plow horse, only to be followed by a cloaked rider he thinks is the Headless Horseman. Ichabod makes it to the enchanted bridge barring the Horseman, who rears his horse and hurls an object, knocking Ichabod off his horse. The next morning, Ichabod’s hat is found next to a shattered pumpkin.

Shawn K. Jain, photo by Jake Nathanson

As he recounts the fable, Jain bends and twists his body to become the lanky Ichabod. He uses certain hand gestures to become the flirtatious Katrina and other physical gestures for the rowdy Brom. "I think what Dev, the director, did is [that] he very smartly guided me to start with the physicality, the physical changes for each character on stage, and then having the voice(s) sort of come from there," says Jain, who’s done voiceover work.

Audiences might find it amazing that this is his first time going solo. "It really takes getting used to when you are the only person on stage. You can always kind of trust in other actors when you are doing a play under normal circumstances. You build that sort of camaraderie," he explains. "But when you are doing a show by yourself, you don’t have another person on stage to act with. I’m playing one person, and I step to the side [now] I’m playing another person. I’m having dialogue basically with myself."

Jain says that "The Legend of Sleepy Hollow" is one of those timeless stories. "I think what this play and the playwright has done really brilliantly is bring up the question of why is it that certain stories stick with us? And why is it that certain stories we believe to be true, even though we don’t have any reason to believe that they are true? Why do conspiracy theories exist? What happens when the line between what’s true and what’s false becomes blurred? "There is a fictional aspect of it, but there’s also an emotional truth to the tale," adds Jain, who gave up a career in marketing and public relations to pursue acting professionally.

"The Legend Of Sleepy Hollow" is a short story first published in 1819 as part of The Sketch Book of Geoffrey Crayon, Gent., a collection of 34 essays and short stories, along with Irving’s other famed fable, "Rip Van Winkle." While he is primarily remembered for short stories, Irving also penned an extensive biography of George Washington.

As a part of his exploratory research, Minigan immersed himself in "who Irving was and what the town and the world was like when Irving was there," compared to now. He traveled to Sleepy Hollow to get a sense of the town and visited Irving’s Sunnyside home in Tarrytown.

Audiences will walk away from the play having been entertained, that is his hope. "It's an American classic for a reason. I also hope they'll see what Washington Irving was getting at. That when you hear a story, when someone tells you something that is emotionally powerful, you have to consider the source. You have to consider what's the agenda of this person. And every listener can't be passive, but really active and exercise good judgment. I think ultimately, it's a play about what happens when you judge things wisely versus when you judge things unwisely or decide not to judge them at all. So, for me, I think that’s the biggest takeaway in America in 2024."

The production features scenic design by Matthew J. Fick, prop design by Emmett Grosland, costume design by Allison Esannason, sound design by Mark Fifer, and lighting design by Emily Clare Gocon, with production stage manager Arielle Legere.

Mile Square Theatre is offering a special “Pay-What-You-Will” performance on October 3, and an Artist Appreciation Night on October 4. General admission is $35 through October 6, and then $45 for all performances thereafter. Tickets are available for purchase online.

Devanand Janki (Director)


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