A Play Worth Losing Your Head Over! The Legend of Sleepy Hollow

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By:Nazifa Hoque & Joyce Li

This September, a headless horseman is riding into Williamsville East High School. The drama club is staging “The Legend of Sleepy Hollow,” and judging by the cast’s enthusiasm , audiences should  expect more laughs than screams on November 13 and 14 at 7:00 PM.

Cast members describe the show as a “fun, comedic, mysterious rom-com.” That’s a lot of genres for one play, but it’s a mix that gives nearly everyone in the audience something to enjoy, whether they come for the jokes, the romance or the mystery of who or what is really riding through the woods at night.

A Classic Tale, Retold

The story has haunted American readers for two centuries. Washington Irving first published “The Legend of Sleepy Hollow” in 1820 as part of his collection “The Sketch Book of Geoffrey Crayon, Gent.” The tale is set in Sleepy Hollow, a quiet Dutch settlement in New York’s Hudson Valley. It follows Ichabod Crane, a lanky and superstitious schoolmaster who competes with the bold local hero Brom Bones for the affection of Katrina Van Tassel, the daughter of a wealthy farmer.

Hanging over the whole village is the legend of the Headless Horseman, said to be the ghost of a soldier who lost his head to a cannonball during the Revolutionary War and now rides out each night searching for it. Irving famously never says for sure whether Ichabod’s terrifying encounter with the Horseman was supernatural or whether someone in the village was playing a trick. That uncertainty has kept readers guessing ever since and has made the story a favorite for adaptations on stage and screen.

East’s production leans into the lighter side of the legend, and the students bringing it to life are clearly having fun doing it.

Meet The Cast

For junior Elliot Chapman, who plays Joseph, the goal is simple: to get the audience laughing.

“I’m excited to try and make people laugh by playing a very dumb student,” Elliot said.

Comedy runs through many of the smaller roles, too. Anishka plays Floris, and while her part isn’t the biggest, she says she makes every line count.

“I don’t have many lines, but the lines that I do have are filled with sarcasm,” Anishka said.

The rom-com side of the show gets a boost from junior Sarah Gelfond , who plays Beatrix. She describes her character as a romantic on a mission.

“It’s a really fun,  flirty, comedic character to play,” Sarah said.

Some of the show’s action takes place in a village tavern, and two cast members spend their time on stage there. Sophomore Izzy Hill  plays the tavern waitress, and this production is a milestone for her.

“I’m excited because I got lines this year, and also because ‘Sleepy Hollow’ is awesome and everybody should come watch it,” Izzy said.

Claire plays Tavern Dweller 2, but her contributions don’t stop when she steps off stage. She is also helping create the look of the show.

“I’m really excited to help with makeup and art,” Claire said.

Claire’s work is a reminder that a school play is built by more than the actors in the spotlight. Costumes, makeup, sets and props all help transport the audience from a school auditorium to an 18th-century village where the woods might be haunted.

More than a ghost story

What stands out when talking to the cast is how much they’re enjoying the lighter moments. Irving’s original tale is often remembered as a spooky story, but it’s also full of humor. Much of that comes from Ichabod himself, a nervous, hungry and easily frightened schoolmaster whose imagination often gets the better of him. By calling their version “a fun, comedic, mysterious rom-com,” the cast suggests that this production brings that humor to the forefront while still keeping the question of the Horseman at the center of the story.

From sarcastic one-liners to flirtatious schemes to a student who isn’t exactly the sharpest in the class, the show promises plenty of characters worth watching, even before a certain headless rider appears.

Overall, the  message to the student body is clear: everybody should come watch it!