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Op-Ed: When Billy Joel was my boss (kind of)

Louis 'Uncle Louie' Gregory worked for Billy Joel in his youth.
Louis ‘Uncle Louie’ Gregory worked for Billy Joel in his youth.
Louis Gregory

It was 1996, and I was a scrappy, overly confident young guy with dreams bigger than my résumé. The Mac was still a novelty, Billy Joel was already a legend, and I had just landed my “first job” in the music business by force of will.

Maritime Music, Billy’s company, operated out of a big red barn tucked away in Southampton, New York. And while I hadn’t technically been accepted into the college internship program yet, I decided to show up early, months early, and boldly told the staff, “I’m your new intern!” It wasn’t a total lie. I just hadn’t been selected yet. But I was there, ready to hustle, and sometimes that’s what it takes.

That gamble paid off in more ways than I could have imagined.

Inside that red barn, I scanned every single one of Billy Joel’s lyric pages into the computer, one by one. It took hours, days, weeks. But I got to read the words of a musical genius up close, long before they were etched into memory by fans around the world. Watching his HBO documentary now, those lyrics come flooding back. He may not remember me doing that, but I’ll never forget it.

READ MORE: Billy Joel documentary ‘And So It Goes’ hits screens this summer

I worked on the Greatest Hits Volume III album. I assisted with his Elton John collaboration. I opened his fan mail, helped manage gifts from fans, including an absurd number of commemorative jackets, and answered phones. One of those calls was from Viktor, the real-life clown from Leningrad.

Oh, and if you ever received an autographed photo from Billy in the ’90s, I may have helped. Let’s just say the autopen and I were on a first-name basis.

Some days, I’d walk Christie Brinkley’s fan mail downstairs to Peter Cook’s office. More than a few of those envelopes were Playboy covers, oddly enough, requesting her signature. Meanwhile, Billy would drive me around in his Jaguar like it was no big deal. His daughter Alexa, who was around 10 at the time, would sit with me at the Mac while I taught her how to use it. Those were simpler times, and every moment was surreal.

One of my favorite memories was helping Billy with a deeply personal project: designing beautiful wooden boats. It showed me that artistry isn’t limited to just one medium. That lesson stuck with me.

Eventually, the “real” intern, the one the program had actually selected, showed up. Things got a little awkward, sure. But by then, I had made myself indispensable. I had proven that passion and persistence can open doors even when the invitation hasn’t arrived yet. But still, Billy’s office manager fired me. I thought my hustle and grit would have prevented that, but they let me go. I often wondered if Billy knew how I hustled my way in, or if she was too embarrassed to tell him. I theorized that he would admire my hutzpah.

The lessons I learned inside that red barn shaped the rest of my life. I went on to work with some of the biggest names in music and entertainment and to produce some of the most iconic events in history. But no matter how high I climbed, I never forgot where it all began.

It started with guts, grit, and a little red barn in Southampton. And to this day, I continue to hustle my way in when all else fails, and I never accept that anything is impossible for me, another kid from Long Island.

Later in life, when I was inducted into the Sachem High School Hall of Honor and then the Suffolk Sports Hall of Fame, I laughingly recalled how it all started with The Piano Man. While I worked on musical arrangements with The President’s Own Marine Band and produced the music for the Presidential Inauguration, I constantly thought about Billy. His influence was always there, like a silent chord beneath everything I composed.

While writing my memoir with Chris Vaccaro on Long Island, we constantly joked that someday we would make sure Billy knew my story. I hope he does. I hope he knows how important he was to my journey. And I hope he knows that after 9/11, I stepped away from music and entertainment to fight terrorism, a break that turned into a two-decade mission to help ensure our beloved city was never attacked again. Then, twenty years later, I got back to work chasing my dreams.

Louis “Uncle Louie” Gregory is a talent manager, music producer, and actor.