Into the Barrel

Jewish teen literature is rife with action-packed thrillers that feature terrorists, kidnappers, sadistic Nazis, hate-filled Arabs, and so on. But, as Yaakov points out, we have no fictional heroes with the iconic status of a Mickey Mouse or Superman.

He believes Pickle Boy fills that niche. Our children are brought up to revere gedolim as their heroes. But many kids, especially those more inclined to the world of action than the world of study, also appreciate a more relatable hero, one closer to their own age, who crusades for truth and justice in a tangible, hands-on manner.

The adventures of Pickle Boy, which each run about half an hour, hearken back to the days of old-time radio serials like the Lone Ranger, with compelling narration, sound effects, and a lot of the same charm. Pickle Boy’s story is presented as a story-within-a-story. The narrator, Uncle Moish, has been asked to babysit for his nine-year-old nephew Eli. When it’s time for bed, Uncle Moish offers to tell Eli a story. Uncle Moish tells Eli, “I haven’t told it to you yet because I didn’t think you were old enough. In fact, I haven’t told it to anyone else either.”

“Can’t you just read me a book?” Eli says. He is sure that listening to a story will be boring. There aren’t any pictures, and he’s been hoping to look at his dinosaur book.

“You can make up the pictures in your mind,” Uncle Moish says.

Uncle Moish launches into the story, with occasional interruptions from Eli as he asks a question or makes a comment.

“I leave a seed of doubt in my listeners’ heads as Uncle Moish relates this crazy story,” Yaakov says, “The boy in the story is also named Moshe, like the narrator, and it comes out that they both have a sister named Miri. Did these wild events really happen? Is Uncle Moish really Pickle Boy?”

The young Moshe of the story lives in an apartment building, until one day his parents manage to scrape together the money to buy a somewhat decrepit house in Flatbush — a house no one else wanted because there were ominous rumors about it. But Moshe’s family moves in anyway, as it’s the only place they could afford.

One day Moshe’s parents go out with his sister, leaving him alone in the house. He decides to explore the basement, and by accident discovers a secret tunnel leading to a room full of barrels of… pickle juice!

“Why pickle juice?” we ask Yaakov. “Do you love pickles?”

“I do like sour pickles,” he admits. “But that wasn’t the reason. It just seemed like kind of a funny thing.” (He has actually approached a couple of well-known pickle manufacturers to ask if they would like to offer sponsorships for Pickle Boy. No bites so far. But Pickle Boy merch — T-shirts, cups, and whatnot — may come your way in the future.)

In the story, Moshe tastes the pickle juice. (After young readers queried, “How could he taste something that isn’t kosher?” Yaakov expanded the story to include that the house’s previous owner was frum, and has Moshe find a paper with kashrus certification lying near the barrels.)

Moshe suffers no immediate effects from ingesting the pickle juice. But the next day, on the way home from school, he takes a swig of pickle juice for a quick snack, and a short time later, he and his friends are attacked by a non-Jewish gang of teenagers. He gives one of them what he expects to be a wildly inadequate punch, but the guy flies clear across the street! And none of the thugs were able to hurt him!

When he accidentally falls into one of the barrels of pickle juice, even his clothes become indestructible. Moshe realizes that the pickle juice has endowed him with extraordinary strength for a limited amount of time, transforming him from mild-mannered Moshe Greenberg to Pickle Boy! Before long he’s living a double life — refined yeshivah bochur by day, and in times of crisis, Pickle Boy.

Thus begin the Secret Adventures of Pickle Boy, battling playground bullies, Mafia bosses, hostile media, and all manner of other nefarious villains. Before long, the bad guys also want to get their hands on the pickle juice, which was invented by an acquaintance of the house’s previous owner in an attempt to help cure people with paralysis, except that it turned out to have extraordinary effects on healthy people.

Moshe is an ordinary kid with many ordinary challenges that kids will relate to, even when he’s not battling forces of evil. Sometimes he has to deal with bullies in his yeshivah, and since the bullies’ parents are big supporters of the yeshivah, those boys never get punished as they deserve. His friends pressure him to use his abilities to give the bullies what’s coming to them, but he resists. His victories are both internal and external.

Adult listeners have remarked that Yaakov portrays the bullying experience with great nuance, as Moshe repeatedly stands up to bullies in his own way. Yaakov doesn’t see himself as particularly psychology-minded, although he does his best to tailor his storytelling to the level of his young listeners (he estimates the ideal age to start listening is about seven or eight).

“In any classroom, you have the problem kids, the bullies,” he says. “They’re a fact of life. Pickle Boy has powers, but he can’t always use them in his personal life.

“Sometimes it’s not enough just to have extraordinary abilities. When Moshe has a nightmare about a bad guy threatening that although he can’t hurt Pickle Boy, ‘I can still hurt your mother and father!’ Moshe realizes his Pickle Boy identity must absolutely remain a secret to avoid retribution.

There are some poignant moments, such as when Pickle Boy saves New York from cataclysmic destruction, and his parents don’t know if he is still alive.

“There’s sad violin music in the background, and it’s really heart-wrenching,” Yaakov says. There is also the element of mystery, as readers wonder: Could Uncle Moish be the same Moshe as in the story? He tells the story as if it really happened, he has a sister named Miri, and Eli overhears him having strange exchanges with his sister in which he urges her not to reveal certain things.

Also, unlike your typical story, most episodes don’t tie up neatly at the end, and the listeners realize that they are joining Moshe on a long journey with many challenges, all to (hopefully) be resolved… at the right time, as the storyteller, Uncle Moish, repeatedly needs to tell his nephew Eli.

While Pickle Boy seems like a Jewish version of Superman, Spiderman, or Batman, Yaakov doesn’t like the term “superhero.”

“It doesn’t seem like a Jewish concept,” he says. “I like to think that the pickle juice doesn’t create new abilities for Moshe, but rather enhances his own latent abilities, in the same way a person with an adrenalin rush might be able to lift a car off a loved one. There’s no ‘magic’ in these stories that isn’t mirrored by feats of strength in Tanach — Shimshon, for example — or acts of kishuf we read about in the Torah.

“We all have kochos. The challenge in life is to decide what you’ll use your kochos for.”

Furthermore, as a thoughtful, yeshivah-educated, committed Jew, Yaakov wants his stories to contain more food for thought than the typical beat-the-bad-guys superhero story. Moshe is often confronted by thorny dilemmas. For example, he only has a limited supply of pickle juice. How should he ration it in the most sensible way so that he can effectively maintain justice and safety in the world?

“Pickle Boy is full of Torah values, but it’s not a mussar shmuess disguised as a story,” he says. “The values are subliminal, and are brought out through the uncle-nephew dialogue.

“The series makes kids think about what they would do if they had a magic potion like Moshe’s. If you had the chance to do something big, would you choose to do the right thing?”

The Spinner of a Thousand Strands

When asked where the inspiration for Pickle Boy came from, Yaakov shrugs.

“I guess that, like many people of my generation, I was exposed to comics and television series as a child,” he admits. “I used to read the Hardy Boys mysteries and other stories of kids doing exciting things, and I liked to imagine myself doing things like that.” He remembers that in fifth grade he was given an assignment to write a story about another child. He decided to write about one boy’s terrible-horrible day in which everything goes wrong. “I realized I really enjoyed creating a story and making up all the things that happen.”

Like his invented hero, Yaakov Bee is a pretty typical born-and-raised Flatbush guy, even down to having one parent who is a Holocaust survivor.

“My father was born in the Warsaw ghetto,” Yaakov relates, “and his family escaped with the aid of local Polish farmers. After staying with them for a few months, it became too risky and they had to go into hiding in the forest, until they were placed in a DP camp after the war. My father was very young and doesn’t have clear memories of these events. He eventually traveled to America and arrived in Minnesota, where he was sent to a day school, but a representative from the Telshe Yeshivah came to town recruiting, and at age 12 he decided to go. He ended up becoming a talmid chacham with semichah from Rav Moshe Feinstein ztz”l. His mother’s father, also a talmid chacham, served as the rav of a small shul.

As a child, Yaakov attended Yeshivas Torah Temimah and Torah Vodaath under Rav Avraham Pam ztz”l. When asked if he had heroes as a child, Yaakov pauses to reflect.

“There was no one person in particular,” he says. “As a kid I admired sports stars, but as I got into mesivta and beis medrash, I developed a deep admiration for Rav Pam. I spoke to him often, and it amazed me that someone could be such a gadol b’Torah and at the same time be so approachable, menschlich and normal. In fact, that became a theme in Pickle Boy: be great, but be very normal and menschlich.”

He was also inspired by the legendary Rabbi Eli Teitelbaum a”h, the founder of Dial-a-Daf and leader of Camp Sdei Chemed, a summer camp in Eretz Yisrael that Yaakov attended as a teen as a counselor and learing rebbi. Rabbi Teitelbaum was a fount of innovative ideas for disseminating Torah and inspiring young people.

As a teenager, Yaakov read widely, and it occurred to him that maybe he could come up with a story about a kid who is special in some way.

“But I wanted it to make sense, to be based in reality,” he says. “My hero’s own abilities could be enhanced by something, the way athletes take Gatorade, or even Pickle Juice (as in the recent Bike for Chai race) to boost their performance. It would have to come with plusses and minuses just like everything in life.

“I used to dream up these ideas at night as I was drifting off to sleep,” he says. “Of course, as a teen I was more simplistic, but I would think up various twists and turns of a plot.”

Yaakov was a Pirchei leader under Rabbi Pinchas Wallerstein, and a counselor in Camp Agudah under Rabbi Simcha Kaufman in the 1980s, and during those years he began telling stories to the boys.

“I started writing my ideas in a notebook 40 years ago, laying out all the plot points,” he says. “I still have it, and I now have a notebook for each adventure. Of course, these days I scan the notebooks into my computer.”

Was he creative in other ways? Yaakov smiles. “Well, I’m a CPA, and there is such a thing as creative accounting,” he jokes. “Back in Camp Agudah I always participated in color war, and I’d write grammen. When my kids were young, I used to make up little songs for them as I changed their diapers or played with them.”

Yaakov earned an accounting degree from Touro College in 1990, where he was the valedictorian, and went on to earn his MBA. He got married in 1991 and worked for a large accounting firm, where he was once given a vocational test. His unusual results suggested his strengths were in both accounting and creative work. He currently works as a finance executive for a Manhattan-based family firm.

Like many a frum balabos, his life is very full. A few years ago, he began leading a Daf Yomi shiur every morning in Khal Zichron Mordechai (known in the neighborhood as Rabbi Sherer’s shul, now led by Rabbi Yekusiel Bittman after Rabbi Sherer’s recent move to Lakewood), which he prepares for in the evenings. He and his wife have six children, five of whom are married, and a gaggle of grandchildren. (“My children don’t want to hear anything more about Pickle Boy,” he confesses. “But my grandchildren love it.”)

But Yaakov is not particularly interested in talking about himself. Why talk about the prosaic life of a Flatbush accountant when he can talk about the exciting adventures of Pickle Boy?

Pickle Boy followed him into his adult life, because as his family grew, he started to tell Pickle Boy stories to the boys in Greenfield Meadows, their bungalow colony.

“We wanted to have an Avos U’Banim program on Shabbos before Minchah, but it would be a challenge to get all the boys to show up on time after being outside all day on those long Shabbos afternoons, and it was kind of hefker,” he relates. “So about 15 years ago I had the idea to first bring them all in for a 45-minute story, and this way they would be on time for learning. As I retold my stories, I did have to update them and refine them from their original Camp Agudah versions of the 1980s.”

Using his original notes, Yaakov expanded with more plot points and elaborations on the backstory, and made the decision to relate Pickle Boy as a story within a story. Those groups in the bungalow colony were his test drive, and led to the establishment of a Shabbos afternoon learning program back at home, with Pickle Boy storytelling followed by learning before Minchah in Khal Zichron Mordechai.

As Pickle Boy’s popularity grew and he saw children going wild for action novels like Harry Potter, Yaakov thought Pickle Boy might appeal to a wider audience. He turned Moshe into “Danny,” and created a secular book under the pseudonym Jack Bee. It took him a few years to write the book, but it pushed him to further expand and elaborate Pickle Boy’s adventures. He added the character of Danny/Moshe’s sister Miri, and a host of other side characters. (The presence of Miri helps draw in the female fans.) His mother, who had been an English major in college, edited the manuscript for him, and he had a simple cover designed.

Yaakov tried to pitch the book to secular publishers such as Scholastic, but in a very competitive market, he didn’t find a taker. Instead, he self-published in 2013. Since covers sell books, he felt it needed something more compelling. Yaakov found an artist to design a more dramatic cover, and a new version came out in 2019. Again, he made a serious effort to get it published by a mainstream publisher, but nothing panned out. It’s not easy to gain traction as a self-published author, and although sales were satisfactory — in the 1500–2000 range  — it just wasn’t worth the effort to continue the process.

A child actually suggested that he produce audio versions of the stories. When Covid hit and thousands of children were sitting home bored, Yaakov decided to begin a nightly broadcast of Pickle Boy adventures. Between his shul email list, bungalow colony list, and then word of mouth, it didn’t take long before hundreds of kids were listening. His 7:30 session lasted half an hour — right before a popular Zoom learning sessions for kids given by a rabbi — and the parents were thrilled.

“The timing was not intentional, and I only found out afterward that many kids joined the learning sessions right after my program was over.”

Yaakov put up a Pickle Boy website complete with news, a Purim costume contest (the winner would be invited onto the show), and a contact button for kids to submit their questions. This went on for about four months, and Yaakov received reams of grateful emails from parents.

In 2023, Naki Radio — now Naki Audio — gave Yaakov his first opportunity to reach a much wider international audience.

“Naki was the first to take a chance with me,” Yaakov says with gratitude.

Moshe Eisenberg of Naki Audio couldn’t have been happier. “It was an instant hit. Every new episode spikes, with thousands of kids from all over the world listening,” he says. “There are kids who organize listening parties when a new episode comes out. As for parents who feel their kids are overdosing on their Pickle Boy listening, we have a ‘downtime’ feature that allows parents to turn it off.”

The following year, 24Six also began streaming his episodes, and Pickle Boy took off; 24Six has logged nearly seven million streams since it began playing on the popular personal listening device.

Every so often, Yaakov does a specialty episode filled with fun facts about Pickle Boy. Sometimes he reads letters from children, or interviews kids. He is also considering doing an episode of Pickle Boy bloopers.

Yaakov includes his Pickle Boy email address at the end of each episode, and many children write in. Their emails have shown him that they are listening b’iyun! They ask sharp questions, which he sometimes needs to address in later episodes (such as asking how Moshe could taste a pickle juice that had no certification, or wondering if Pickle Boy is Mashiach).

How the Magic Is Made

Yaakov met us at the home of his Pickle Boy partner-in-crime, Rabbi Chaim Itzkowitz, who helps record, edit, and embellish every episode of Pickle Boy. Chaim has a small studio at the front of his Flatbush home equipped with mics, computers, and a comfortable office chair where Yaakov sits to record.

“When I first began recording for Naki, my producer was a friend’s tech-savvy teenage daughter,” Yaakov says. “But when she started her senior year of high school, I knew she was going to become extremely busy, so I enlisted the help of Chaim, the son of one of my chavrusas in my morning kollel.”

The young, multitalented Rabbi Chaim Itzkowitz learns in Rabbi Mordechai Zucker’s kollel in the mornings and is a halachah rebbi in Yeshivas Ohr Yitzchak in Brooklyn. He teaches chassanim, plays music at weddings, and writes plays and musicals for schools. During the summers, he runs a division at Camp Ruach and gives the staff shiur.

Rabbi Itzkowitz takes Yaakov’s raw audio clips and adds in music and sound effects for a richer experience. He will even spend money of his own to buy sound effects and, when necessary, records himself playing music or making sounds. Occasionally Yaakov offers suggestions for exciting music to create the right atmosphere.

“Over time, we’ve learned each other’s style and expectations,” Yaakov says. “We’ve developed a synchrony. But for me, the sound effects aren’t the main emphasis. The story is the ikar.”

Yaakov is not a particularly large man, but he has a big, resonant voice that’s perfectly suited to dramatic storytelling. Rabbi Itzkowitz does not alter Yaakov’s voice except in the case of Eli, the little boy listening to the story, to make him sound younger. Yaakov is very adept at modulating his voice to suit the different characters, and has a natural storyteller’s ability to create excitement for Pickle Boy’s escapades.

“I do different voices, but I don’t exaggerate,” he says. “There are no gimmicks, just an exciting story.” He does admit that when he sits alone in the small studio he has to work harder to summon up the same level of energy and drama that is usually generated when he performs in front of a live audience.

When asked if he ever thought about including actors in his audio clips, as entertainers like Shmuel Kunda a”h used to do, Yaakov shakes his head.

“First of all, Pickle Boy is told as a bedtime story,” he says. “Most of it is the voice of Uncle Moish telling Eli the story. Also, it’s not easy to involve child actors, who have to be brought in by their parents and can’t always be expected to be professional. Chaim and I both have busy lives, and sometimes we don’t get to record until 10:30 at night, which also precludes using child actors.”

Unlike some storytellers, Yaakov doesn’t leave anything to chance. He writes out his 45-minute scripts and follows them without improvisation.

“Chaim and I are both perfectionists,” he avows. “We try to get episodes out as fast as we can, but since I put so much detail into them, it’s basically like writing a book for each season,” he says.

The recordings depend on Rabbi Itzkowitz’s busy schedule. Once the season is mostly complete, they make the effort to put out a new episode every two weeks, to give themselves time to complete the season while the early episodes are running.

The results are clearly compelling. A family in England emailed Yaakov to tell him they had driven from their home to the Alps, a 15-hour trip, without a single fight or complaint, because the children were listening to Pickle Boy for the entire ride.

Yaakov is currently busy producing Season 3 of Pickle Boy for Naki Audio, and believes he has enough material for at least six seasons. “I think I could write 13 books,” he says.

Riding on the success of the audio clips, Israel Bookshop Publications is moving forward with a frum version of Yaakov’s original secularized Pickle Boy book, containing the plot of Season One. A few elements — references to internet access, some name calling, and some of the more violent content — have been excised, but the main content is the same. The book is slated for release around Chanukah time, so that on long winter Friday nights or summer Shabbos afternoons — when streaming episodes isn’t an option — Pickle Boy fans will still be able to lose themselves in his adventures.

But what happens when Yaakov runs out of Pickle Boy ideas? He says he has a few ideas for different adventures, such as Planet Kvetch, the story of a kvetchy kid whose NASA-employed father accidentally blasts him off to a planet of kvetches. The boy learns that the only way he can survive there is through reverse psychology — for example, if he wants a doughnut, he has to tell people, “I hate doughnuts!”

The sky’s the limit for Yaakov’s outsized imagination, and he’s clearly excited to see Pickle Boy capture the hearts of his young listeners.

“I told my wife, ‘I’ll know I really made it when we get a free Pesach out of this,’” Yaakov says.

As for his eager listeners, he makes sure to tell them, “I give you a brachah to be me’ayen in Gemara like you’re me’ayen in Pickle Boy.”

(Originally featured in Mishpacha, Issue 1075)