A Day in the Life of “Master Storyteller” Jonathan Kruk

We shadowed the omnipresent performer in the hours leading up to ‘Irving’s Legend’

It’s hard to miss Jonathan Kruk as he walks through Sleepy Hollow, cutting the figure of a gentle giant adorned with thick sideburns, a tailored pale-olive suit, ruffled shirt, and vest. “Yesterday, I went out in the whole regalia and I got stopped all the time,” Kruk confirms over lunch alongside his musical accompanist Jim Keyes at local diner/pizza shop The Horseman.

Even when the self-proclaimed “Master Storyteller” isn’t masquerading around town, he remains recognizable across Westchester. In the build-up to both his annual Halloween-time staging of Irving’s Legend (his riff on Washington Irving’s Legend of Sleepy Hollow, complete with original music from Keys) at Sleepy Hollow’s Old Dutch Church and early winter rendition of Dickens’ Christmas Carol at nearby Reformed Church of the Tarrytowns, his visage can be seen on countless banners, his eyes characteristically bugged out and arms raised overhead.

He’s just finished Legend‘s first Sunday matinee, one of 50 October performances in all. This time of year, the Headless Horseman is all around him, from the statue of its likeness across the street to the actual stunt horseman who clods around town throughout the month. 

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Photo by Evan Poholchu

“This is where the Horseman rides,” he remarks admiringly, in an aptly soft, narrator’s tone. He loves all this hubbub, and why not?

Kruk, who grew up mostly in Katonah and currently resides in Cold Spring, started telling multiple Irving tales as part of Historic Hudson Valley’s programming way back in 1995. In 2010, the organization moved him into the Old Dutch Church, at which point Kruk focused solely on Irving’s Legend each fall. 

“That, for me, was a godsend, one of the best things that happened professionally,” he recalls of the location change. “It’s given me so much recognition. It’s advanced my career. And I want to do it for as long as possible.”

For Kruk, seasonal gigs reviving Irving’s Legend and Christmas Carol complement a variety of storytelling jobs throughout the year. He and his wife, actress Andrea Sadler, will soon perform as the Mad Hatter and Queen of Hearts at the Planting Fields Arboretum’s Camellia Festival on Long Island. Recently, he even entertained a group of preteen girls at a safari-themed birthday party at the New York City townhouse of one of the girl’s fathers, a hedge-fund magnate.

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Kruk’s no stranger to those kinds of gigs. Between his first storytelling appearance in 1981 and the early 1990s, he estimates having been booked for at least 100 birthday parties a year. Though his very first, for a 6-year-old girl, didn’t bode well.

“I said, ‘I’m going to tell Cinderella,” Kruk remembers. “I saw something winging through the air, and then whack! I got hit in the head. It was the older, jealous brother saying, ‘We don’t need to hear that! We have the video!’ He threw it at me and hit me in the head.”

He’s had no such dustups with pre-K kids, for whom he performs “finger fables” at summer camps, libraries, and schools by creating rabbits and turtles with his hands. “You should see Jonathan with kids,” says Keyes, an actor and storyteller himself in addition to providing music for Irving’s Legend. “It’s really magical.”

Kruk’s fascination with the craft began by telling his younger brother bedtime stories. While studying at Holy Cross in the mid-’70s, he ducked into a bookstore and found a story titled “East of the Sun, West of the Moon.” Later that night at a party, as Kruk relays, he cracked open a Narragansett beer and, under the bottle cap, found an image reading “East of the sun, west of the moon.” At that moment, he knew what he was meant to do.

Photo by Rudolf Von Dommele

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His main inspirations since have been the late Boston street performer Brother Blue, as well as Jay O’Callahan, who’s held audiences captive for years by voicing an array of characters. “It was just masterful to see a solitary soul telling a story and doing all the characters,” says Kruk of O’Callahan. “And I loved to think about how I could do that.”

Today, he embodies more than a dozen in Irving’s Legend alone, with visitors coming from as far as Minnesota to bear witness. As evidenced in his matinee, kids lean forward in their pews, awe-struck, as Kruk relies on a handful of props, but primarily his voice. Plus, it’s all in his head. Kruk rarely rehearses before shows. And if he did, he wouldn’t have much time on this occasion, as his lunch at the Horseman wrapped up just in time for the curtain to rise on his next invocation of Legend.

Fortunately, he doesn’t have far to go, and he promptly heads back down North Broadway toward the Old Dutch Church, where he has become part of the local tableau. “One fan once said in years to come, I’ll be a spirit here, but through the residual energy that I’m imparting on the place,” Kruk says, flattered by the notion. “Not a haunting spirit like the White Lady or the Headless Horseman, but this creative presence that people will have in their conscience.”

For more information on Kruk and when and where he’s performing next, visit his website

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