On The Table Read Magazine, “the best entertainment eBook magazine UK“, Joel Samberg discusses his new book, Jackie Jester, in which a gifted but troubled songwriter navigates the highs and lows of a unique musical career.

Written by JJ Barnes
I interviewed Joel Samberg about his life and career, this inspiration behind his new book, Jackie Jester, and his creative writing process.
Tell me a bit about who you are.

I’m a 67-year-old kid who loves to write. A dedicated scribe who avoids clichés like the plague and is as stubborn as the day is long. By that I mean I never accepted a nine-to-five job that didn’t have writing as a major component. And as many writers know, even the best of us more times than not need nine-to-five jobs.
When did you first WANT to write a book?
I wanted to write as young as seven or eight. Since that time, so much of what I observed, overheard, saw on the news or in the neighborhood, or simply wondered about I turned—in my head at first—into books and plays and movies and TV shows. That’s just the way it was. I have no explanation for it.
When did you take a step to start writing?
When I was thirteen I wrote a screenplay called “Crooked Dreams” (a musical western, no less), sent it to MGM, and received a very encouraging letter in return.
How long did it take you to complete your first book from the first idea to release?
My first published book was an assignment with a deadline, so it was really a case of working as fast as I could to turn in as good and complete a manuscript as possible.

How long did it take you to complete your latest book from the first idea to release?
On one hand, Jackie Jester was a lifetime in the making. On the other hand, it was a full two-year process from the first draft to the published book. I grew up on the fringes of the record industry and had a lifelong interest in music. So the idea of a multi-generational narrative in which the recording industry is a key player has always appealed to me. But I also had a deep desire to write a story about my grandfather’s unusual career. His name was Benny Bell, and he had a few novelty song hits through years, such as “Shaving Cream” and “Everybody Wants My Fanny.” He wrote, arranged, sang, played the guitar, cut the disks, designed the record labels and album covers, created the ad campaigns, and often drove the records around to record stores. His life and career were ripe for a novel. So I combined both ideas, and result is Jackie Jester.
What were your biggest challenges with writing Jackie Jester?
The most challenging part of writing Jackie Jester was resisting the urge to include many more narrative elements, characters, and backstories about the industry in general, as opposed to focusing almost exclusively on the character of Jackie Jester. But I decided it would be much more effective and emotional if the world of the novel was Jackie’s world only. So I kept it at that level, while weaving in just enough of the industry to convince readers that even Jackie’s little world had to exist to some extent within the bigger professional world.
Who or what inspired you when creating your Protagonist?
The protagonist was inspired by my grandfather, Benny Bell, a novelty singer and songwriter who had a fascinating up-again/down-again career that, despite mostly being down, lasted almost 70 years.
Who or what inspired you when creating your Antagonist?

The antagonist was created by combining imagination with speculation on some of the people my grandfather may have run into along the way.
What is the inciting incident of Jackie Jester?
Arguably, there are several inciting incidents in Jackie Jester: when young Jack discovers that his silly songs are popular with his classmates; when his father passes away unexpectedly; when his best friend from childhood comes back into his life; when he has a hit record; when his son makes some startling discoveries about his life and career….
What is the main conflict of Jackie Jester?
The main conflict is that a fascinating, dedicated career can be so fraught with some of the most miserable lows, such enormous highs, anger, humor, and perplexing crossroads. In the novel, as a teenager in Depression-era Manhattan, Jack makes a name for himself writing silly songs. That’s why he decides to devote his life to making records. Before he turns 20 he becomes the comic yet troubled driving force behind Jester Records. His first hit record leads to a hookup with a shady character who takes over the company. That’s when Jack starts to lose his heart and soul. He eventually gets them back—but it is too late? Will his loyal wife Ellie remain devoted? Will his hero-worshiping son David continue to adore him?
Did you plot Jackie Jester in advance, or fly by the seat of your pants and write freely?
With everything I write I usually have a specific beginning and an equally specific ending. The rest, much of it unplanned, comes to life during the writing process.
Did you get support with editing, and how much editing did Jackie Jester need?
The publisher engages a professional editor. (I, too, spent years as a professional editor and, in addition to the publisher’s editor, do one pass on the manuscript as an editor instead of as a writer.) Plus, I personally engaged a few experts on music, records, and radio to read the final draft to assure the accuracy of many ideas and descriptions.
What is the first piece of writing advice you would give to anyone inspired to write a story?
Promise yourself that you’ll commit to taking advice from people who know what they’re talking about, that you’ll have a thick skin for rejection, a willingness to put your story away for several weeks or months before reading it again with a fresh pair of eyes, and that the one and only reason you want to write is because you have a burning desire to.
Can you give me a hint about any further books you’re planning to write?
I am putting the finishing touches on a new novel called Remember Me to Herald Square. It’s about a young newspaper reporter and a young actress who were high school sweethearts in rural Ohio who find themselves in New York City. Can their romance be rekindled, even though it appears that their careers are on an unintentional collision course?
And, finally, are you proud of your accomplishment? Was it worth the effort?
I’ve never wanted to do anything else. I may have a few issues with the world of professional writing and publishing these days, but despite that, I still manage to derive much joy from bringing my characters and stories to life between the covers of a book. There’s nothing quite like it for someone like me. If just three people in the world tell me they enjoyed the literary journey with one of my books, then yes, it’s fully worth the effort.
Pop all your book, website and social media links here so the can find you:
Apple Books: https://apple.co/3G4mnCb
Kindle: https://amzn.to/42yF3Tj
Paperback: https://amzn.to/4iZdvw1
Hardcover: https://amzn.to/4jsPxcE
Jackie Jester Blog: https://jackiejester.blogspot.com/2024/09/blog-post.html
Joel Samberg Amazon Page: https://www.amazon.com/stores/Joel-A.-Samberg/author/B000APLCG6?ref=ap_rdr&isDramIntegrated=true&shoppingPortalEnabled=true
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The process of writing Jackie Jester sounds intense and personal. Has Joel ever considered writing a prequel or spin-off about other music industry characters featured in the novel?