By Matthew del Negro
Photographer: Andrea Ceraso
It’s hard to believe that I was only introduced to Sam Hollander, via text, in mid-August of this year. And given that he graduated from my former arch-nemesis high school, Fox Lane – I’m a John Jay grad – it’s shocking that I admitted to liking him so quickly. To say that we hit it off from the first phone call is an understatement. Though vastly different in our approaches to life and career, we discovered several bonds in common, the first of which was that we had both been raised in northern Westchester – Sam in Bedford Hills, while I was born in Mount Kisco Hospital and raised in Pound Ridge.
…Out of the blue, a former lacrosse opponent of mine, Harry Dunne, who was a year behind Sam at Fox Lane, had reached out to me to tell me that he had run into his old buddy Sam, and said that Sam had recently moved back to Bedford. He said that, given Sam’s circuitous route through the music industry on his way to topping the charts with hit songs he’d written, there might be some parallels to my own story of navigating the entertainment industry as an actor at the speed of molasses. In short, he identified two misfits that could commiserate over their shared failures in sibling industries. He couldn’t have been more dead on!
Matthew Del Negro is a popular actor with scores of hit television and film credits; previously featured on the cover of the January/February 2022 issue of B&NC Mag – available on the B&NC Mag website.
Sam Hollander is a Billboard-chart topping, multi platinum songwriter; previously featured in the Holiday 2019/2020 issue of Bedford Magazine – available on the B&NC Mag website.
After reading Sam’s mile-long Wikipedia page, texted to me by our mutual friend Harry, I was a little intimidated. I play the piano, but Sam’s success in the music biz is a whole different story. Nonetheless, I punched the digits and connected with Sam over the phone. Immediately, as he began to tell me about his new book, 21-Hit-Wonder: Flopping My Way to the Top of the Charts, we both recognized the familiar pattern of starts and stops that I had documented in my own book, 10,000 NOs: How to Overcome Rejection on the Way to Your YES, which was published in 2020. …On top of that, we discovered that the same publisher who had championed my book at Wiley Publishing but who’d opened his own shop, Matt Holt Books, before my book was actually published, was the same guy, Matt Holt, who’s now brought Sam’s book to fruition. Sam and I talked about shared themes and other industry connections, and then we talked about our ‘glory days’ and late-80’s Section 1 sports, and we swapped tales of some John Jay and Fox Lane legends and their current whereabouts. Then we got down to his book.
When he began discussing his legendary flops in the music industry, which are well- documented in the book, I immediately loved his self-deprecating humor. Hearing him tell these stories, in the down-to-earth style and tone he maintains, one would never suspect that the testimonials on his book jacket would be from such superstars as Billy Idol, David Duchovny, and Ringo Starr!
When he began discussing his legendary flops in the music industry, which are well- documented in the book, I immediately loved his self-deprecating humor. Hearing him tell these stories, in the down-to-earth style and tone he maintains, one would never suspect that the testimonials on his book jacket would be from such superstars as Billy Idol, David Duchovny, and Ringo Starr!
THAT’S THE MAGIC OF SAM HOLLANDER!
And it’s the magic of his book! For anyone raising kids in Westchester County, it’s a must- read from a parenting standpoint alone. He talks about the influence of growing up in the country while being simultaneously adjacent to the greatest city in the world. Through hysterical stories, and wearing his vulnerability on his sleeve throughout, Sam writes: “Sadly, I was never the first pick in any litter; academically, musically, athletically, even with girls, shit was always an uphill grind. So, at that fragile age, the stacking of all of my collective non-achievements really began to demoralize. I started skipping out of school and sneaking home early for two-hour depression naps on the daily. My folks didn’t know how to deal with me.”
Though we grew up in neighboring towns, our childhoods, and our paths, were quite different. I was a ‘good little boy’ and wasn’t bitten by the acting bug until after I quit Lacrosse at Boston College, and had to unlearn all my ‘color within the lines’ life-lessons in order to explore an artform that traded more in
shades of gray than blacks and whites. Sam, on the other hand, was a self-described anarchist and non-conformist from the get-go. Hellbent on learning every little factoid about the one industry he ever wanted to be a part of – the music industry. Sam’s childhood was filled with crazy adventures, often propelled by his artist parents and their famous connections. Like how Sam counts Andy Warhol – yes that Andy Warhol -amongst the roster of his former babysitters!
Still, Sam and I similarly describe our defining character trait as adults to be:
irrepressible drive.
DESIRE TO ‘GET OUT’, TO ‘BE SOMEONE’
and it is apparent on every single page of his fascinating book. Unlike my book, which is part memoir, part self-development with takeaways at the end of each chapter, Sam’s is full of wild stories from his young years rubbing elbows with household names while he willed his way to the top. But the beautiful thing about his book is that, amidst the caffeine-filled, late-night grind sessions in the studios, and the failed college stints and near-miss album stories, there are gems of wisdom for emerging artists in the music industry. Actually, there are gems for emerging humans in any industry. The book is, above all else, honest.
For all the hits he’s had and famous people he knows, and all the backstage access he has, Sam exudes a mix of honesty, humility, and humor that disarmingly bely his wild success. Whether as a failed rapper, a failed student, failed athlete or failed love-interest, Sam maintained his sense of self, and his hunger to express the music that he created by melding the tunes that he loved as a youngster. Read the book, if not for the wild stories and the laughs, read it to be inspired to go grab your own dream by the horns and wrestle it down to the earth.
After selling his music catalog for a big pile of dough in 2019 – Sam is back in Bedford. He and his wife, Jen, decided to eschew the too- digitally-social environs of Los Angeles in order to raise their daughter, Joey, back in the more wholesome environment of Sam’s childhood. I’m sure there’s a small part of the returning hero, pleased to return – successfully – to the place where the varsity football coach cut you from the team and said you were a ‘loser who wasn’t going anywhere’. But mostly, Sam is thrilled to be able to do things like take a walk with the family on Reservoir Road , and that Joey has found a circle of real friends and a great place to go to high school. His book tour is taking most of his time these days – and all of the proceeds from the sale of the book will go to the charity Musicians On Call. But, as always, Sam’s also busy writing, collaborating and recording. Driven as he is, Sam’s got plenty yet to come!
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