Sinatra and Me

"I loved Tony’s book. It's fun and paints such a vivid picture of the times that I felt I'd actually just spent a weekend in Palm Springs with Frank…and still have a hangover."
—George Schlatter, former producer of the Grammy Awards and of Rowan and Martin's Laugh-In

Auteur

Tony Oppedisano—a.k.a. "Tony O"—is a former professional musician and singer who went on to become an award-winning producer, served as a member of Frank Sinatra’s management team, and also managed comedian Don Rickles. *Tony was only twenty-one when he first met and befriended Frank Sinatra. Tony later became the singer’s best friend and road manager, a contributor to two of Sinatra’s platinum albums, and a producer of the documentary *To Be Frank: Sinatra at 100. Tony grew up in Brooklyn, New York, and currently lives in Los Angeles.

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An intimate, revealing portrait of Frank Sinatra—from the man closest to the famous singer during the last decade of his life.

Résumé
An intimate, revealing portrait of Frank Sinatra-from the man closest to the famous singer during the last decade of his life.

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Chapter 1: Of All the Gin Joints

CHAPTER 1 Of All the Gin Joints

The Beginning of a Friendship

It was November 1974, the end of Frank Sinatra’s self-imposed “retirement.” He’d walked away from his performing career in 1972, believing his music was no longer relevant to the younger generation. Two years later, twenty thousand people bought out Madison Square Garden to see Sinatra on his comeback tour. ABC sportscaster Howard Cosell was emceeing that night. The concert was billed as the Main Event, and Cosell announced it like a boxing match. I was twenty-three years old, sitting a few feet from the stage, in the block of seats Frank reserved at concerts for his friends and family. I’d known him for two years by then. Spending time with him at Jilly’s, a Manhattan club, I’d gotten to know the private Sinatra. I was about to see a very different man. I knew about the power he radiated onstage, but seeing it up close was a different matter. The dichotomy of the two Sinatras, onstage and off, was mind-blowing. My pulse raced with excitement.

The crowd was restless, waiting for the moment when Frank would appear. Then suddenly he was there, materializing in the center of the arena, and I felt the air electrify. The crowd came to its feet and roared loudly enough to shake the walls. Frank was dressed in an impeccable black tuxedo, black bow tie, and orange silk pocket handkerchief. I knew that the handkerchief bore his likeness and signature. He wore one at every performance to give to fans who brought him flowers onstage. A small thank-you. He began to sing “The Lady Is a Tramp” as the crowd gradually quieted to hear him. In spite of the large arena, it felt intimate, personal. Frank had a knack for making everyone in the audience feel like he was singing just to them. I was riveted. It was magic, and I was a part of it.

My father once told me he should have known I’d end up hobnobbing with the rich and famous. He liked to kid me about it.

“From the time you were born, you liked classy things.”

“What do you mean, Dad?”

“Two hours out of your mother, you had to have a private suite.”

The private suite in question was my incubator.

I was a preemie, arriving two months early, on September 27, 1951, at Brooklyn Hospital. In a large extended family of brown-eyed, dark-haired, olive-skinned Italian-Americans, I was a standout. My fair freckled skin, blue eyes, and flaming red hair made me easy to identify in family pictures. I got teased about my coloring, but it was never mean-spirited. The only time my parents mentioned my hair was when I’d done something truly bad. When they got frustrated with me, instead of switching to my full name, Anthony Joseph, they’d start referring to me as the “redheaded guinea.” Even at the time, I knew it was tongue-in-cheek. But I also knew I was in trouble.

In many respects, I had the childhood Frank wanted. Until I was twelve, we lived in a two-story brownstone on Brooklyn’s Eldert Lane. Our working-class neighborhood was a mixture of Italians, Jews, Germans, and a couple of Irish families. Like every Italian-American family of the time, our brownstone had pictures on the wall of the Pope and generations of our relatives. Once I discovered Sinatra at age thirteen, there was a photo of him on the wall as well. My godfather, Uncle Joe, lived upstairs with Aunt Fran and their two daughters. Dad and Mom and my brothers and I had the main floor, and we all shared the basement.

There was a reassuring rhythm to our weeks. Every Friday night, the whole family went down into the basement for parties with lots of food and music. I’d carry food up and down the stairs from the kitchen, where my mother, aunts, and paternal grandmother were cooking. The men supplied the music. With my uncle Joe strumming the mandolin and my dad on guitar, they played a lot of popular tunes from the twenties, thirties, and forties, mixed with a few Italian tunes like “Santa Lucia.” Sometimes Uncle Al chimed in on his banjo. What they lacked in skill, they made up for in enthusiasm. On Sundays, my big brother Pete and I got up early to be at Blessed Sacrament, where we were choirboys.

On weekday nights, if we got our homework done, we could watch TV until nine. My favorites were always the variety shows, like Ed Sullivan, Red Skelton, The Dean Martin Variety Show, and later Carol Burnett. Even at that age, I had a strong affinity for show business. I loved watching comedians like Jackie Gleason and George Burns. I enjoyed guessing where they were going with a joke and noticed how they were developing a specific bit. I had a secret hope that some Hollywood agent would discover me. In later years, I teased Frank about it. I told him I could have played the Eddie Hodges part, the little redheaded boy singing “High Hopes” with Frank in the movie A Hole in the Head.

Frank laughed and said, “Well, you’re probably right, but I didn’t know you then.”

I put on my sad face, sighed, and said, “I know.”

In many ways, we were the typical all-American family of the Eisenhower years, but I was also fiercely proud of my Italian heritage. People knew that the best way to get my attention was to call me Irish. A teacher of mine would spell my name O’Ppedisano just to get my goat. As the only family member who didn’t really look Italian, I knocked myself out to make my ethnicity clear. I was the only one of my paternal grandmother’s twelve grandchildren to learn Italian. My first words to Frank were in Italian. I learned everything Italian, from the music to the cooking. When I grew up and started playing in the New York clubs, I’d switch over to the mandolin and strum Italian songs when the wiseguys showed up, just to make it clear that though I might not have looked Italian-American, we shared a heritage.

I also learned the Old Country superstitions. The most feared superstition was malocchio, the evil eye. When people gave you the evil eye, bad things could happen. If you got a headache, it was because someone was talking badly or enviously about you. If you were complimented by people who were jealous of you, you were in danger of malocchio. There were several ways to prevent it. You could put your hand in your pocket and shape your fingers like a horn. Or you could wear a horn on a chain around your neck along with a crucifix. Every Italian neighborhood had those guys wearing “wifebeater” shirts and gold chains…