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“You are only given a little spark of madness, you must never lose it”… Robin Williams
The point of this interview with iconic, song writing…now music royalty Sam Hollander is “Never Give Up”…which is probably also one of the points of his book “21 Hit Wonder: Flopping My Way to the Top of the Charts.” Although his book was released in 2023 “it” and “he” just recently came to my attention while on the set of “Profiles With Mickey Burns.” However, this is one of those books that keeps on inspiring like the energizer bunny, and so does Sam.
Panic At The Disco, Ringo Starr, Billy Idol, One Direction, Weezer, Katy Perry, Daughtry, Carole King, Train, blink 182, Fitz and the Tantrums, Gym Class Heroes, Def Leppard, Jewel, Boys Like Girls, Train….are among some of the artists Sam has collaborated with in song writing endeavors. With 23 US charted top 40’s, and 10 #1 hits.
Within moments of listening to him I knew he was a gladiator in an arena of brave souls who had the courage to step out of the shade into the light unafraid. He slipped through the song tunnel, down its wild corridor of reality until he landed in the seat of the music bringing with him just the right amount of genius and madness to make it work.
Mickey Burns (MB): In your book, you said, “I was finding new ways to fail, but I wasn’t repeating mistakes.”
Sam Hollander (SH): I was a visionary when it came to flopping in new and inventive ways. But I made sure not to repeat mistakes, which was key because failure is such a massive part of the process. Early on, I was hanging out in Greenwich Village, watching bands in my network get signed and either blow up or fade away within months. I spent years mentally playbooking what I’d do if I ever had a hit.
MB: How did you turn consistent failure into consistent success?
SH: Time, space, and adapting my craft. I studied multiple genres at a time when most people were hyper-focused on just one. I was pulling from disco, soul, classic rock, new wave, hip-hop, and folk rock—always trying to infuse those elements into every song.
MB: You’re a real student of music.
SH: I’m a total nerd. My influences weren’t necessarily in line with mainstream pop, but then iTunes arrived in 2004 and changed everything. Suddenly, the singles chart mattered again, and I realized that if we wanted to compete with artists like Destiny’s Child or Justin Timberlake, rock songs had to hit differently. Once that door opened, the calls started coming in.
MB: Andy Warhol used to babysit you?
SH: That’s probably how I got my book deal. It’s a fun reveal. My mom was an interior decorator, and her business partner, Jed Johnson, was Andy’s life partner. On weekends, while my mom and Jed went antique shopping for work, they’d leave me at Andy’s apartment. So there I was, in the kitchen with Andy, two dogs, and a couple of maids.
MB: Did you know how famous he was at the time?
SH: Oh yeah, I knew. I also knew he wasn’t particularly thrilled to be babysitting me. I was just an appendage he didn’t need. But I still thought it was the coolest thing ever.
MB: When did you know you wanted to be a songwriter?
SH: From the moment I heard Magic by Pilot at age three. Music became my obsession, but in the ’70s and ’80s, there was no clear roadmap to a career in songwriting. I’d see names like Diane Warren and Desmond Child on records and wonder, How does someone become Desmond Child?
MB: Now people are asking, How do I become Sam Hollander? What’s your advice?
SH: Become Desmond Child! Honestly, I’d say, stay hyper-attuned to the world. Inspiration is everywhere—conversations in restaurants, books, documentaries. If you’re really listening, the words will come to you. Everything I’ve ever written was a message in some way.
MB: What’s Billy Idol like to work with?
SH: The definition of cool. He rolls up on his chopper, super soft-spoken, sweet, and fun. If you’re lucky he arrives with Steve Stevens, who’s also a legend. These guys were posters on my childhood wall—now, here I am working with them.
MB: Katy Perry?
SH: Whip-smart, super lyrical, and hyper-impressive.
MB: Jewel?
SH: The hardest-working writer I’ve ever met. We started at 1 PM, had two songs done by 6:30, and by 9:30, my engineer called to say she hadn’t left and wanted to write another. So I rushed back, and we worked until 1 AM. She’s an incredible lyricist and an amazing person.
MB: That kind of work ethic explains her success.
SH: Absolutely. I’ve worked with over 500 artists, and the ones who truly succeed are the ones who sprint into the room like Flo Jo in ’88. They’re driven, focused, and relentless. If you don’t have that wiring, it’s much harder.
MB: What about Train?
SH: Pat Monahan is one of my closest friends and probably one of the most gifted songwriters alive. He’s the full package—melodic, lyrical, and hilarious.
MB: And Ringo Starr?
SH: Absolute legend. Just as cool as you’d expect.
MB: How did you get to write a song with him?
SH: Have you seen my chiseled features?
MB: What was your first big break?
SH: Carole King. That was the moment someone in the industry took me seriously. Within a year, I went from an outsider to writing with an icon. Just knowing that legends saw something in me gave me the motivation to keep going.
Eileen Shapiro (ES): Best experience after writing a song for an artist?
SH: Sailing with the Kennedys. Train brought me along when we did Save Me, San Francisco and Marry Me, and my wife and I spent the day sailing with them. It felt like I was on acid—in the best way.
ES: Most embarrassing moment working with an artist?
SH: Meeting Cyndi Lauper before I had any success. She walked into my studio, took one look at me, and said, There’s a Starbucks on the corner, honey—go get me two Frappuccinos. Suddenly, I was a delivery boy. But she was hilarious—it was all in good fun.
ES: You like to get to know artists before writing with them. How deep do you go?
SH: It’s all about research. Once we’re in the room, I hope we click, but I’m a realist. Some of these people become lifelong friends, and some I never see again. But I always make sure I’ve done my homework and respect their artistry. They can tell when you genuinely care.
ES: Why did you write the book?
SH: Initially, as a historical record for my daughter. I wanted her to understand that this journey wasn’t easy—that it was full of agony, but also incredible moments. Then, as I kept writing, my career kept evolving, and I realized I had something valuable to say to young creatives. I started speaking to students and saw that the messaging they’d been getting about the industry wasn’t realistic. I wanted to be honest—it’s an amazing adventure, but it’s brutal. If you don’t have the tenacity, do something else.
ES: I read somewhere that you play guitar?
SH: Barely. I know four chords—enough to write a song alone if I have to. But collaboration is where I thrive. I actually just wrote a song for Noah Kahan and Sesame Street that debuted last night. Elmo has a lot of currency on Instagram, by the way.
ES: If you could collaborate with anyone you haven’t yet, who would it be?
SH: Mickey Burns, obviously. Beyond that? I’ve worked with so many of my idols—The O’Jays, Tom Jones, Billy Idol, Violent Femmes. At this point, I get most excited about working with young, hungry artists. Watching someone rise is the best part of the job.
Interview by Mickey Burns and Eileen Shapiro
