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 with crosses and horns. The color red also warded off the evil eye.

Aunt Fran was the only one in the family who knew the ceremony to dispel malocchio. The neighbors would come to see her when they were the victims of malocchio. She’d fill a soup bowl with water and a small bowl with olive oil. Taking two drops of olive oil, she’d say a prayer, murmur something in Italian, and drop the oil in the bowl. When the oil hit the water, it would form shapes, and I’d see a pair of eyeballs. I can’t explain it, but I really did see eyeballs. Within a half hour of Aunt Fran’s performing the ceremony, the person’s headache nearly always went away. I asked her to teach me the ceremony, but she said it could only be taught on Christmas Eve—and in the excitement of Christmas, I always forgot. Too bad. It would have come in handy in Hollywood.

Did I actually believe all this stuff? Not really. On the other hand, what could it hurt to take a few precautions? When I had my very first tuxedo made, I had it lined in fire-engine red just to be safe.

Our lives were also shaped by the Catholic Church. We attended mass regularly, and all the kids in our family went to parochial school through sixth grade. I was a good student, but I found school boring. It didn’t challenge me. I never took notes. At an early age, I discovered that I possess a somewhat photographic memory. It’s been both a blessing and a curse. Most of my teachers were nuns. You do not mess with a nun. You have to grow up Catholic to understand. Catholic boys learn at an early age to respect women, even more so when they’re Italian-American and raised by strong mothers and grandmothers. Frank understood that. He didn’t respect anybody as much as he respected his mother, Dolly.

I was an independent kid, always my own person, and I never worried very much about what other people thought of me. Maybe it was the hair. I was never going to fit in, so why even try to be like everyone else? Even as a small boy, I had my own sense of style. In the summer, I’d wear shorts if I was playing a game, but otherwise, whether or not it was a school day, I wore cotton or wool pants with a crease and a dress shirt with long sleeves. Sometimes I’d add a bow tie. I didn’t even own a pair of jeans until I moved to California when I was twenty-four. Frank got ridiculed with the nickname “Slacksie” when he was a kid for always wearing dress slacks. I never acquired a nickname, but I was easy to find in a crowd of kids. I’d be the only one playing baseball in slacks with a crease.

I was something of a loner. Sometimes I’d find myself feeling lonely even in the midst of all those loving family members. It was like loneliness was a disease, and music was my medicine. When I was happy, I turned to music. When I was sad, I turned to music. It was always in my head, and I couldn’t turn it off. I needed it like most kids need food.

At age four, I started to play the piano. We had an old player piano in the basement of our brownstone, and I’d go downstairs and noodle around on it. When I heard music on the radio, I could figure out how to translate it to the keyboard. At one Friday-night party when I was about five, I sat down on the piano bench and played a popular Lawrence Welk song called “Sailor” that I’d learned from the radio. My family was astonished. They knew I liked to fool around on the piano, but they didn’t realize how much I’d learned on my own. As I practiced more, the structure of music came naturally to me. The piano made sense to me because it was the most wide-open instrument, all right there in front of you, measured in exact intervals. When I was about nine, I moved to the accordion. I initially took up the guitar because of the song “Sleep Walk,” by the Ventures, an instrumental group that was very popular at the time. I loved the song, and I wanted to play it, so my uncle Joe loaned me his guitar. I was about twelve years old. I learned the guitar literally one string at a time. Once I unlocked the transition between the piano and guitar, figuring out what the comparable keys and intervals were, I could play it. The mandolin was next. The violin, viola, and cello were each a different challenge since notes aren’t measured on them like they are on a piano or a guitar, which has frets. You have to rely on your ear. Once I made that transition, the rest was easy. The bass and banjo followed. If it had strings, I could play it.

We moved out of Brooklyn to Long Island when I was thirteen, and I made the transition from Catholic school to public school. The change of schools came at just the right time for me musically. In junior high, I met Joe Costanzo, a music teacher who taught during the week and did weekend gigs on keyboard. He inspired me to pursue my passion for music. The year I turned thirteen was also the year I discovered Frank Sinatra’s music. My rendezvous with fate occurred at a Woolworth’s department store in Franklin Square. I was looking through record albums after school one day when I stumbled across one of Sinatra’s and bought it for $3.95. When I got home, I immediately went down to the basement and put it on the record player. On the first cut, Frank started a cappella with the title song, “The Nearness of You.” The piano then joined him, followed by the entire orchestra. At that, I went, “Wow!” It was a rich, deep, full-textured sound, and there was an electric buzz in Frank’s voice. From then on, I was hooked.

I started thumbing through the stacks of 78s that my father kept in the basement. He’d collected a wealth of Sinatra tunes performed with Tommy Dorsey’s orchestra and even a couple with Harry James. Whenever I had the money, I’d buy another one of Frank’s albums. I bought out everything they had at Woolworth’s. I still own over one hundred Sinatra vinyls, a good number of which I acquired in junior high and high school. Listening to the records was a fascinating journey back to Frank’s roots. I found that I wasn’t enthralled with the timbre of Frank’s voice on the early albums, not only because of the primitive recording technology, but also because his voice was a lot higher and thinner then. Listening to Frank’s later songs, I could hear how far he’d come in perfecting his craft.

The year I entered my teens there was another big change in the Oppedisano family. After growing up with two brothers, I acquired a sister. Angela was born in 1964 and came to us at three weeks old as a foster child. When she was five, we adopted her. Angel, as we came to call her, and I had a special bond from the very beginning. Because of the age difference, I was more like a father than a brother to her. We may not have been related biologically, but Angel and I had such similar personalities, it drove me crazy sometimes. She was a little pistol. Losing her twenty-five years later was one of my life’s hardest losses. It left a hole in my heart that remains unfilled.

I started high school in Floral Park, Long Island. School was still easy for me, and I usually got all of my homework done in study hall. If I finished early, I’d go to the music room and practice on the various instruments. I also sang in the choir, where I became a soloist and the student head of the choir. In those years, I formed an especially close relationship with Fran Walker, the literature teacher. Because there wasn’t a full-time drama teacher, Fran was assigned the job of producing that year’s musical, Bye Bye Birdie. Knowing of my interest in show business, she asked me to help. I rolled up my sleeves and went at it. It was the first thing I ever produced, and I tackled it with the confidence of a teenager who has no idea what he’s getting into. It meant working with an orchestra, putting together a light scheme, rehearsing elaborate choreography, and coordinating everything else that goes into a musical.

The play calls for an Ed Sullivan voice-over, and one of my first jobs was to get someone to voice Sullivan’s part in the play. He had one of the most famous voices in show business, and unfortunately, there was no one in school who could do his voice well enough to suit my taste. So, being young, stupid, and fearless, I decided to call The Ed Sullivan Show and see if they’d help me out.

The guy who answered the phone that afternoon was named Santullo, a fellow Italian-American. I explained that I was producing Bye Bye Birdie for my high school out on Long Island and needed some help.

“Here’s my predicament. I have a lot of respect for Mr. Sullivan and wouldn’t want to have someone impersonate him badly. So I thought I’d call and see if you could help.”

Mr. Santullo started laughing.

“Did I say something funny?”

He answered, “No, no. I was just impressed with your level of professionalism. Hold on a second. I think I might be able to solve your problem.”

He put me on hold. I was drumming my fingers, listening to the canned music, when a different person came on the line.

The man said, “So, young man, what’s the problem?” You couldn’t miss the voice. It was Ed Sullivan. Mr. Sullivan listened to my explanation, then said, “No problem. We’ll remedy that right away. Give me your address.”

A few days later, I received a package containing a quarter-inch tape reel with the lines from the play, recorded for me by Ed Sullivan himself. When I played it, the familiar voice boomed throughout the theater: “And now, right here on our stage…” It was terrific.

I learned an important lesson about producing that day, one that served me well later: It’s amazing what you can get if you’re willing to ask for it. Especially if you have a lot of moxie and don’t know any better.

It turned out I’d need that edge, because despite having top grades, I almost didn’t graduate from high school. The teacher who taught my computer class threatened to flunk me because I spent my extra time in the music room rather than the computer lab.

He knew I left study hall whenever I finished my homework early, and one day he asked me, “What are you doing leaving study hall?”

I answered, “That time’s my own. I use it to go down to the music room and play the piano to clear my head.”

“What for?”

“Well, because I love music, and I love show business.”

He looked down his nose at me and said pointedly, “Show business is superfluous.”

I still remember his words, and I remember replying, “No, you’re superfluous.”

He wanted his revenge. He threatened to flunk me so I wouldn’t have enough units to graduate, even though I was doing well in the class. Luckily, Fran Walker campaigned on my behalf, and I ended up graduating with flying colors.

It was also during high school that I experienced my first real tragedy. My godfather, Uncle Joe, no longer lived upstairs from us, but we’d remained close after the move from Brooklyn. An amateur musician himself, he’d always encouraged me in my music. From the day I was born, he’d always been there, just up the stairs when I was little, his arm around me in family pictures, his guitar or mandolin in my hands. Then, when I was sixteen, he was diagnosed with lung cancer. Every male Oppedisano before him had died of cancer. He’d been a lifelong smoker. The cancer was already very advanced and was untreatable. The doctor told him to make the most of the time he had left by traveling and enjoying himself. Uncle Joe wouldn’t accept the doctor’s advice. He’d watched family members die in pain, and he knew what it had done to them and the family. He wanted to spare himself and our family that ordeal, either by dying quickly or by getting better. Uncle Joe asked the doctor to perform surgery on his lungs, but his doctor refused, saying he probably wouldn’t survive the operation. The doctor told Uncle Joe it would be unethical to operate on him. Uncle Joe then started seeing doctor after doctor, all of whom refused to operate.

Finally, he found a doctor who agreed to do the surgery. The family suspected that Uncle Joe hoped he wouldn’t survive the operation. It was pretty clear the doctor didn’t think he would, either, because full payment was demanded up front.

Against the odds, Uncle Joe survived the surgery, but it would have been better if he hadn’t. He was unable to take care of himself anymore and lived in constant agony. Aunt Fran couldn’t cope, so I began taking care of him. I cooked for him, helped him eat, dressed him, helped him in and out of bed. He was too weak to stand in the shower by then, so I gave him sponge baths. Afterward, I’d dry him off, dress him again, and put him to bed. I had no idea at the time that taking care of Uncle Joe would enable me to help Frank someday. Near the end of Frank’s life, as his health failed, he’d reach out to me for assistance with some of those same things. Frank was very private, and it was easier for him to accept help from a friend and surrogate family member than from a caregiver. It was my honor to help him through those difficult times.

When classes started again that fall, I’d call from a pay phone at school every day, to check on Uncle Joe, before I walked home. In the second week of October, I called him as usual when school got out. Aunt Fran told me Uncle Joe wasn’t up to talking, but I could talk to him, let him hear my voice. What she didn’t tell me was that Uncle Joe had almost died that morning but had been hanging on, waiting for my call. Ten minutes after I hung up, on October 11, 1968, my godfather, Joseph Oppedisano, passed away.

The funeral was at St. Catherine’s of Sienna. It was the first time I attended a funeral for someone I loved like a part of myself. I was stunned with grief, and most of the day remains a blur. The only thing I remember is, after the service, walking down the aisle with my father, following the coffin. My dad, who’d always struggled to show me affection, reached out and took my hand as we walked, squeezing it tightly. I held on for dear life. I’m not sure which of us needed the other one more in that moment, me or my dad.

I sought refuge from the pain of Uncle Joe’s passing the way I always coped, by throwing myself into my music. I formed a little trio with my older brother, Pete, and another kid from school, Gary Berzolla. We started performing at sweet sixteen parties and other local gigs. The band didn’t last long. I’d had great hopes in the beginning, but after a while, it just wasn’t challenging me enough. I’d begun to explore more complex music. I knew by then, with absolute certainty, that music was my destiny. It would be many years before my father accepted that, but I already knew where my path would take me.

When I was seventeen, I started going into the city and making money doing gigs as a jazz guitarist in some of the clubs. We moved to Ronkonkoma the next year. New York driver’s licenses didn’t require pictures in the sixties, so it was easy enough for me to get a “license” saying I was eighteen, the minimum age to play in the clubs. All the clubs had pianos at the time, and I could always double as a pianist if they needed one. My father still didn’t like my chosen profession, and he pushed hard to get me to go to engineering school. That was never going to happen. New York beckoned, and with it, my dreams of making it in show business. I didn’t know it yet, but my life would soon change forever. Forty-seven miles down the Long Island Expressway and over the Fifty-Ninth Street Bridge, my future was waiting in a reserved booth at Jilly’s.

It was December 8, 1972, and I was twenty-one years old the night I met Frank Sinatra. Frank was in the middle of his self-imposed (and short-lived) retirement at the time. I, on the other hand, was just getting started. By then, I’d been performing in clubs professionally for four years. I was already making a bit of a name for myself working all over the tristate area. Some close friends and I had put together a little band that included a keyboard player, Les Stanco, and a drummer, John Bonelli. I was also working as a vocalist by then. I’m a baritone with, coincidentally, the exact same range as Sinatra, note for note. It made it easy for me to sing the standards I’d always loved.

The early seventies were an amazing time for a musician in New York City, which boasted a wealth of nightclubs. There were clubs that leaned toward jazz, and also society rooms like Danny’s Hide-A-Way. These nightspots appealed to the New York upper crust and were destinations for celebrities, artists, writers, and wealthy people in general. A good number of the elite hotels had showrooms. Even at the Waldorf, they had the Empire Room, where Sinatra, Ella Fitzgerald, and Sarah Vaughan had played. Nowhere else on earth could a musician have experiences like I was having almost every night. Of all the clubs, though, Jilly’s was, to me, the most special.

At 256 West Fifty-Second Street, just off Ninth Avenue, Jilly’s was on “Jazz Street” in the Manhattan club district. Jilly’s always offered terrific music, the best musicians, and an eclectic crowd. There’d be “twenty years of good behavior” at one table, a senator at another, and a concert pianist at another. It wasn’t unusual for people like Tony Bennett and Judy Garland to sit in with the band for a set. Jilly ran a good club. One thing he never did was water down the booze, and he had a great reputation for playing straight with the customers. He’d once worked as a bouncer, but as he got older, he learned alternate ways to defuse situations.

A guy would come into his club, get drunk, and become abusive. Jilly would go quickly to the person and say, “Hey, come on, let’s relax. Let’s not do this. Come on, let’s go to the bar. Let me get you a drink. And let’s calm this whole situation down.”

There was a code that Jilly had worked out with “Uncle Frank,” his brother, who was usually behind the bar. Jilly would walk up to the bar with the troublemaker and say, “This gentleman is having a drink with us.”

Uncle Frank would make the guy a very special drink. He kept some horse physic hidden behind the bar that was used to loosen an animal’s bowels when it had colic. Frank would put a drop or two in the drink and hand it to the troublemaker. As Jilly said, by the time the guy could say, “Holy crap,” it would be running down his legs. It’s hard to be a tough guy when your shoes are filling up with shit. Jilly didn’t have to throw the guy out. He couldn’t get out of there fast enough.

By the early 1970s, Jilly’s was one of the hottest clubs in town. Walking up the sidewalk to Jilly’s, you saw an orange canvas awning, shading a glass door. Under the awning, as solid as a fixture, stood the doorman, Sy. Sy was a tough guy whom you didn’t fool with: six feet four inches tall and solidly built, dressed in a uniform, cap, and long gray coat with braid that went all the way to his midcalf. If you got past Sy and through the first door, you went down a couple of steps to a second glass door that led into the club. Over the second door hung a framed magazine cover of Frank Sinatra and Princess Grace of Monaco, Frank’s former costar, Grace Kelly. Inside the club and on the right was a bar, always crowded. The wall opposite the bar was covered with framed photos, some of Jilly, but most of Sinatra with various celebrities, dignitaries, and heads of state, as well as framed production stills from his films. If you looked closely, you’d notice that the frames were all screwed into the wall. Jilly knew someone would lift the photos if he turned his back.

On the left was a little open coatroom with a hat-check girl. Past the coatroom and the photo wall was a doorway that led you downstairs to where two pay phones nestled inside oversized clamshell enclosures. Beyond them on the left were a card room, men’s and women’s restrooms, and the kitchen. There was a metal tube going down to the kitchen like they used to have in navy submarines, allowing the waiters and maître d’ upstairs to communicate with the cook downstairs. If you wanted to get the cook’s attention, you’d pull out the cork at the speaking end of the tube and whistle, and he’d shout back up. There was also a service elevator downstairs that came up to street level in front of the club, to the left of the orange awning. Jilly had to use the elevator to smuggle Johnny Carson out of the place one night when Johnny had the misfortune of flirting with a mobster’s girlfriend.

If you kept walking past the photo wall upstairs, you’d come to a maître d’ stand in front of an archway with another door. Screwed to that door was a life-sized plyboard cutout of Frank Sinatra. If you got past Frank and the maître d’, you entered the main room, scattered with round two- and four-top cocktail tables. Midway into the room, on the left-hand side, was a baby grand piano encircled on three sides by a shelf, small tables, and chairs (referred to as the “piano bar”), under a ceiling mirror that was cut in the shape of a baby grand. It was like looking at twin grand pianos on the floor and ceiling. Customers could sit around the piano and sip their drinks, taking in the music. Beyond the piano bar were three more rows of cocktail tables, and on the rear wall were tufted leather booths. The leather booth on the left was for Sinatra when he was in town. Jilly kept a special orange leather armchair for Frank’s exclusive use, orange being Frank’s favorite color. The chair was normally kept in storage. If you knew Jilly’s and saw that the orange chair was out, you knew Frank was in town. On the rear wall of that booth hung a large movie poster, depicting Frank as Dirty Dingus Magee, sporting a derby and long johns. It was kind of a strange choice of posters. Frank would be the first to tell you it was not one of his most stellar films. In between the booths was a pair of saloon-type swinging doors that looked like they were borrowed from an old John Wayne western. The doors opened to the busing station. That was also where the dumbwaiter came up with the food from the kitchen, and where the metal submarine-style communication tube went down.

I started going to Jilly’s regularly because everyone knew it was Sinatra’s favorite place and because I just liked it. A few weeks after I started coming to the club, I made the acquaintance of Jilly’s brother Frank, who ran the place. Everyone called him “Uncle Frank.” It didn’t take him that long to notice me. I must have stood out a little with my carrot-red hair. Besides, I was always dressed in a tuxedo after my gig and usually smoking a cigar. I didn’t really blend in. Uncle Frank was also a cigar smoker, and that’s how we started our first conversation.

He was pouring me a drink one night and said, referring to my cigar, “That smells good. What is it?” So we started talking about cigars.

Another night, Uncle Frank said to me, “Every time you come in here, you’re in a tuxedo. What do you do?”

I said, “Well, I’m an entertainer, a musician.”

A few nights later, I was standing at the bar, looking at pictures of Jilly on the wall opposite, when I noticed that there was something not quite right with Jilly’s eyes. I asked Uncle Frank about it.

He just said, “Well, he’s got a bum blinker.” He didn’t tell me which eye it was.

I was at Jilly’s so often by then that after a while, Uncle Frank suggested I sit in with the band. It went well, and it wasn’t long before Uncle Frank was telling me, “I gotta introduce you to my brother. You know he’s off with Mr. Sinatra.”

And one night, Uncle Frank did.

He said, “My brother’s comin’ back to the city this weekend. Frank is not gonna be with him, so I’m gonna have an opportunity to put you two guys together. When are you comin’ in?”

I said, “When do you want me to come in?”

The night finally came when I was supposed to meet Jilly. I was at the bar when Jilly came downstairs from his apartment. The bar was three deep with people. I was standing with my back to the bar, looking at the pictures on the wall that I’d looked at hundreds of times before, trying to look cool. Another guy was standing next to me, also waiting for Jilly. Uncle Frank handed me a drink.

Turning to his brother, Uncle Frank said, “Jilly, I want you to meet Tony Oppedisano.”

Jilly and I shook hands, and then he shook hands with the guy next to me.

I went back to minding my business, still looking at the pictures, until Jilly said, “How you doin’?”

I looked at Jilly and then looked away and back at the pictures. I didn’t say anything.

A long minute passed, and Jilly said again, “So how you doin’?”

Again I didn’t say anything. Finally, Jilly slapped me on the shoulder and said, “What! Are you deaf [pronounced deef]? I’m talking to you!”

I blurted out, “Jeez, Jilly, I’m really sorry. Your brother and I were talking about the fact that you have a bad blinker. I didn’t know if it was this one or that one. I thought you were talking to him,” pointing to the guy next to me. I felt like a fool.

Jilly started laughing, put his arm around me, and said to his brother, “Frank, I like this kid.”

He and Uncle Frank and I sat down and chatted for quite a while that night. From that first meeting, Jilly and I hit it off.

Uncle Frank told him what a good musician I was, and Jilly said, “Well, give him some work. Bring him in and put him with some people here.”

So I began working at Jilly’s occasionally, along with all the other clubs. I got to work with guys like Joe Petrone, who played piano. One night when I was working, Joe got sick, and Mickey Deans filled in for him. I didn’t know who Deans was; I only knew he was a good piano player and a decent singer. I found out later he’d been married to Judy Garland for the last three months of her life.

As the place was closing down, Jilly said to me and Mickey, “Listen, I’m going to the after-hours joint down on Houston Street. You guys want to come along?”

We said, “Yeah,” so I left my car at the club. I went with Jilly and some other people, and Mickey met us there later.

The place on Houston Street had the feel of a speakeasy, where you walk down four steps to a door and a guy opens a peephole. Everything in the world was going on inside: card games, slot machines, and plenty of drinking. I’d never seen anything like it. I was still a kid and mesmerized by it all.

When my mind finally started to clear, I noticed it was about six thirty or so in the morning, and I said to Jilly, “Listen, you heading out any time soon? Because I still have to go to Long Island.”

He said, “No, I’m gonna be here for a while.”

Then Mickey said, “I’ll drive you back.” He’d drop me at Jilly’s on his way home to New Jersey.

It turned out that Mickey wasn’t just being a good Samaritan. On our drive back to Jilly’s, he hit on me.

I said, “Listen, I’m flattered, but no, thank you.” When we got back to Fifty-Second Street, I got in my car and headed home.

I thought about the implications of that moment when I found out he’d been married to Judy Garland. Another small piece of the tragedy that was Judy Garland’s final year.

Jilly had been gone from the club a lot in the years before I’d met him, on the road with Sinatra when Frank was still touring. But from late 1971 to early 1973, Jilly was in the club more often because of Sinatra’s temporary “retirement.” Frank was still in and out of New York a lot during that time, and when he was in town, he’d come into Jilly’s after dinner and stay until the sun came up. As I soon witnessed for myself, every time Frank arrived at Jilly’s, he’d follow the same ritual.

Frank would come in the door and immediately walk through the club past the bar, the maître d’, the cocktail tables, the piano bar, and his booth in the left-hand corner. He’d keep walking through the swinging saloon doors, straight to the busing station. Going to the metal tube going down to the kitchen, he’d pull the cork out, whistle into the thing, and wait for Howie to pick up. Howie was the Chinese chef who created tasty Cantonese dishes that rivaled any restaurant in Chinatown. Frank used to claim that Jilly had Howie chained to the stove downstairs. “He doesn’t let him out of there, you know.”

Howie could mangle the English language like no one else. When Frank whistled into the tube, Howie would answer back, “Yes, what you want?”

Frank would say, “Howie?”

“Yes, dis is Howie.”

“Howie, this is Frank.”

“Oh, Frant.”

“Listen to me, Howie.”

“Yes, what, Frant?”

Frank would say in his best impersonation of Howie, “Futt you, Howie.”

And Howie would answer, “Oh, futt you, too, Frant!”

Frank did it every time he came in. When Howie retired, Frank gave him a Cartier watch, and on the back, it said, “To Howie. Futt you. Frank Sinatra.”

Many years later, when Frank and I were in residence at the Waldorf Towers, we started reminiscing about the club. We got to talking about Howie, and Frank said, “I wonder what the hell ever happened to him.”

I made an excuse to go in the other room and started doing a little research. This was before the Internet, but I managed to find out that Howie was still alive and living in Brooklyn with his grandson. I got the number, then went back in the other room, dialed the number, and put Frank on the phone. The minute Frank heard the voice, it was unmistakable.

Howie asked, “Who dis?”

“This is Frank Sinatra. Who is this?”

“Oh, Frant! Dis is Howie.”

“Oh! Futt you, Howie.”

“Futt you, Frant!”

Right off the bat. It was like no time had passed.

In December 1972, shortly before his fifty-seventh birthday, Frank was back in New York, and just as Uncle Frank had decided to introduce me to Jilly, Jilly wanted to introduce me to Sinatra. He knew I idolized the man, and he suggested it, in part, because he knew what it would mean to me. He also suggested it because, as I learned later, he thought Sinatra and I would get along well, be a “good fit.” For a kid who’d been telling his friends for years that someday he’d be friends with Frank Sinatra, Sinatra’s imminent arrival was like the second coming. Jilly said he’d try to set something up.

That same December, Frank Sinatra Jr. was booked for an extended run in Manhattan, four nights a week at the iconic Rainbow Room. With Frank Sr. retired, Frank Jr.’s singing career had started gaining major momentum. As the only male Sinatra out there singing, Frankie Jr. was carrying the Sinatra banner. The gig at the Rainbow Room at 30 Rockefeller Center was a premier booking. It was a dream gig in a beautiful venue with a seventeen-piece orchestra. Junior was doing terrific business, in part because some folks in New York, including me, were hoping that Frank Sr. might show up some night to see his son. With Sinatra out of the business, any sighting of the man was an event.

Somewhere around December 6, Jilly called me and said, “Listen, Tony. Don’t talk it up, but the ol’ man’s comin’ in.” Frank was coming to check out his son’s show in the middle of its run—traditionally, a more relaxed time for a performer. Whatever kinks had existed in the first performances would be remedied by then, and the pressures associated with closing wouldn’t have yet started. “We’re gonna go to the late show Friday, the midnight show. What’re you up to Friday?”

“I’m doing a gig in the city, but I’m done early ’cause it’s a private function.”

So Jilly said, “Well, if you can, try to make it over for the show. Either way, before the night’s done, we’ll end up over at my joint.”

I was so excited at the prospect of actually meeting Sinatra that I was afraid to think about it, for fear I’d jinx it. One thing was sure: come hell or high water, I’d be at Jilly’s Friday night.

When December 8 rolled around, I headed into the city earlier than usual to set myself up for a seat at Frank Jr.’s show later that night. When I arrived at the Rainbow Room, I went up to the maître d’ and introduced myself.

I said, “Listen, I’m doing a gig here in the city. I’m going to be done early. I’d like to have a seat wherever you can stick me to see Frank Jr.’s late show tonight. I’ll be coming in just around the time that he’s going on. Can you help me out?”

The maître d’ said, “Fine, no sweat.” So I gave the guy a twenty—a good tip at the time—to seal the deal.

As soon as I finished my gig that evening, I ducked out and rushed over to the Rainbow Room. As I stepped out of the elevator, I could hear the show starting. Frank Jr. was in the middle of his opening number, and as I approached the maître d’, he motioned for me to follow him into the room. He wanted to seat me right away, but I whispered to him that it wasn’t polite to walk in when a performer was in the middle of a song. I asked him to wait until the first number was over. The room was wall-to-wall people. As audiences in the Big Apple usually do, everyone in the place had dressed appropriately in sports jackets or suits and ties. Looking around the room, I was beginning to feel just a little conspicuous in my tuxedo with the red lining.

That was when I saw him, seated in the audience stage left, just outside the ring of artificial light. He was watching his son, obscured from the view of the audience in the soft darkness. Frank Sinatra. Unmistakable. I felt a surge of electricity go through my body. I was momentarily transfixed. When my mind cleared, all I wanted was to get seated quickly and quietly with no one noticing my late arrival.

A moment later, a captain appeared with a small cocktail table, complete with tablecloth. As Frankie Jr. finished his opening number, the captain said to me, “Right this way, sir.”

He then proceeded to walk through the center of the audience straight toward the stage, carving a path through the press of people, carrying the table with its cloth over his head. A waiter followed with the table setting. I brought up the rear in my tuxedo. As the applause tapered out, heads turned toward us, and both the audience and Frank Jr. watched our little procession in bemused fascination as we inched our way across the room. The silence onstage seemed to stretch interminably. I kept waiting for the floor to open up and swallow me. No such luck.

The captain plunked my table down within feet of the stage. Pretending I was invisible, I sat down all by myself. I could see Jilly out of the corner of my eye, sitting near Sinatra Sr. and watching me. He was shaking his head like, What the f***? The show had shifted from the stage to me.

As if it couldn’t get any worse, a waiter then appeared and said, in a voice that seemed to echo, “May I take your drink order, sir?”

I whispered through slightly gritted teeth, “There’s a show on! Jeez! Just bring me a Jack rocks… please!”

I felt certain everyone in the audience had heard what I’d be drinking that night. I was acutely aware that Frank Jr. was still standing silently onstage, staring at me as if to say, May I continue now? Would that be okay with you? I prayed that through some miracle, his father hadn’t noticed me. Finally, after what felt like a week, Frankie Jr. started his second number, and the audience’s attention switched back to the stage.

It was a great performance, though it didn’t quite play to what a large portion of the audience was hoping to hear. Frankie was terrific, but they wanted to hear his father’s songs. Finally, in the middle of his act, the orchestra began playing the intro to “All the Way.” The audience burst into applause as soon as they heard the opening notes.

Frankie said, “This is what I lovingly call the Sinatra hour.” The applause got even louder, and when it finally died down, he said, “You have no idea how happy I am that you responded like that to what we’re about to do, because you’re a lot closer to Frank Sinatra right now than you know.”

Surprised, I glanced over to where Frank Sr. was sitting. He was glaring at his son. Those blue eyes seemed to give off a laser that could melt a lead wall. Frank Sr. did not want to be outed to that audience. Junior obviously caught the look.

Fortunately, he was quick on his feet and said, “No, you don’t understand. This is Dad’s tux. I borrowed it for this engagement.” That got a good laugh and neutralized the excitement as quickly as it had appeared.

When the show was over, Frank Jr. received a well-deserved standing ovation. But once the lights came up and the audience had a chance to look around, the rumor started circulating that Frank Sr. was indeed in the room. Before anyone could get to him, Jilly grabbed Frank, and they quickly made their way out through the kitchen. In a routine that would become familiar to me, waiters instinctively ran interference, making it impossible for anyone to get over to where they were.

I yelled to Jilly as he hustled Frank out, and Jilly shouted back, “I’ll see you over at the joint later.”

I settled my tab, took the elevator down to the street, got in my car, and went over to Jilly’s. Word must have gotten around quickly that Frank Sr. had been at the show. Jilly’s open-air parking lot next to the club was overflowing, with Cadillacs and Lincoln Town Cars double-parked down the street. Sy had his hands full controlling the crowd as they surged toward the entrance, excitedly anticipating the “Chairman’s” arrival. I threaded my way through the mass of fans to the glass door. As soon as Sy saw me, he opened the door and waved me in. I could see as I went through the second door that people were four deep at the bar. Men and women were crushed together, sporting their finest clothes and jewelry, with enough pinky rings to fill several showcases. Shortly after I entered, Uncle Frank spotted me and handed me a drink over the heads of the crowd. I kept walking, greeted the maître d’, and went to sit at the piano bar. Once there, I tried to relax, but I couldn’t settle. I sat there sipping Jack and waiting.

At about two thirty a.m. or so, I felt the place suddenly come alive with electric energy, and two words spread through the club like a chant: “He’s here! He’s here!”

Sure enough, walking down the steps with Jilly behind him, in the flesh, was Frank Sinatra. I remember the moment vividly. People turned toward him as though they were magnetized. Even those who didn’t realize he was there felt the pull and looked to see what it was. For me, the moment was overwhelming.

Despite Jilly’s best efforts, Frank was getting mobbed. He fought his way past the bar and into the room on his way to his booth, which was just behind me. I was sitting at the tail of the piano as he walked past me.

Somewhat to my own surprise, I heard myself saying in Italian: “Madonna, che gran baccano!” loosely translated as, “Mother of God, what chaos!”

Frank heard me, turned, and said to me, “Can you believe that? You’d think they’d be able to keep people from doing that to me, for crying out loud. But hey, when they stop doing that, that’s when it’s all over.” Then he patted me on the shoulder, smiled, and went to his booth. God bless my grandmother for teaching me Italian.

As Jilly walked past me, he leaned over and said, “We’ll talk later.” Then he joined Frank in his booth.

I glanced over at Frank, trying to be unobtrusive. The man was impeccable. He was wearing a dark blue suit with subtle light blue pinstripes, a pristine white shirt, and a perfectly knotted silver tie with a soft blue diamond pattern. His eyes were a startling azure no head shot could do justice to, his hair showing a few silver strands. Sitting in his usual booth, laughing and relaxed, he gave off a charisma that was like a force field.

I continued sitting at the piano bar, sipping my drink and trying not to stare. Frank’s favorite waiter, John Bianculli, was serving the group. John’s nickname was Johnny Smash. Johnny and I had developed a pretty tight relationship by then, so I called him over.

I said, “Listen, do me a favor. I don’t know if the opportunity is going to present itself for me to meet Frank formally, and God knows when I might be in his company again. I hate to be a civilian, but could you see if you can get Frank’s autograph for me?”

Johnny said, “Sure, sure.”

Johnny knew without my telling him that it would be rude to interrupt Frank’s dinner. When Frank’s group finally finished eating, Johnny walked over to Frank and started talking. As he listened, Frank leaned forward and peeked around Johnny at me. Johnny was nodding his head. In my mind, the conversation was probably going something like this:

“Well, who’s this for?”

“The kid sitting at the piano bar.”

“The kid in the tuxedo?”

“Yeah.”

“Okay.”

I could only pray Frank hadn’t asked, “The kid who interrupted my son’s show?”

Then Johnny handed Frank one of Jilly’s promotional mailers with a printed menu on it, and Frank proceeded to sign it. Johnny read it as he came walking back over to me, shaking his head with a bemused look on his face.

I asked Johnny, “What’s the matter?”

“This guy’s been coming in here twenty years. I’ve asked him for hundreds of autographs. I’ve never seen him sign his name like this.”

He handed it to me, and I read, Hi, Tony. Best, Frank Sinatra, Sr. Johnny pointed at the Sr. after his name.

I knew immediately it was Frank’s way of teasing me, of letting me know, I saw you over at the Rainbow Room making your “low-key” entrance to my son’s show! It was, as I later learned, classic Frank.

By then it was past three thirty in the morning, and Jilly issued last call. Everybody was “invited” to leave except for a select group.

As the club closed, Jilly got up from Frank’s booth and came over to me. He leaned in, putting his hand on my shoulder, and said, “So, you got your ax [guitar] in the car?”

“Yeah, why?”

“Well, he”—he nodded his head in the direction of Sinatra—“feels like hanging out, and I’d like him to hear you play.” My mind started racing. All I could think was, Damn, I’ve been sitting here drinking Jack Daniel’s for the last two hours. If only I’d had a clue. I’m going to embarrass myself. Here’s my big moment, and I’m going to blow it.

I went out to my car and got my guitar and amp out of the trunk. I brought them back into the club as they were settling tabs, chasing people out wholesale, and clearing the room. By twenty minutes after four, the doors were locked, and the only people left were Uncle Frank behind the bar; Johnny Smash; me; Joe Petrone on piano; Lou Berriman, the great bass player; Jilly; Frank; and a young lady to whom I was never introduced. It was just the three of us playing: Joe, Lou, and me—piano, bass, and guitar.

I started making sure my guitar was tuned up. Like I often did in clubs, I went downstairs and lifted the telephone, tuning the guitar to the dial tone. Then I came back up and sat down on the street side of the piano, facing Frank’s booth, and plugged into my amp. Joe Petrone was just finishing a tune when I sat down. Frank, Jilly, and Frank’s lady companion got out of their booth and moved up to the piano.

I tried my best to put my anxiety out of my head and concentrate on going into work mode. Joe, a consummate professional, picked a tune, called a key, counted it off, and we went. We moved seamlessly from one number to the next, picking up on each other as experienced musicians—especially jazz musicians—know how to do. It was going really well. Joe and I, having played together before and each knowing how the other thought musically, instinctively knew how to stay out of each other’s way. Tune after tune, the first half hour whizzed happily by. Then, just as I was relaxed and basking in the glow of the music, the unimaginable happened.

Joe turned to me and said, “Hey, Tony, why don’t you play something by yourself?”

For a moment, my mind went utterly blank from sheer terror. Fortunately, I had a lifetime of music and hundreds of Sinatra songs stored away in my head, and something came to me out of the blue. I remembered an album Frank had recorded with composer/guitarist Antonio Carlos Jobim, a record I’d worn out from playing it so many times. There was one song, entitled “How Insensitive,” that I knew was a particular favorite of Frank’s. My fingers instinctively found the strings, and I started to play it in Frank’s key, chords and melody together.

As my fingers moved over the frets, I began to hear a soft hum. It took me a moment to realize where it was coming from.

When it hit me, I almost dropped the guitar. It was coming from Frank.

I thought to myself, Is anything else going to happen to me tonight?

Here, just a few feet away from me, was that rich baritone, coming across the piano in unison with my playing. I looked up at Frank. He had his eyes closed. He was leaning back, completely in the moment, humming the beautiful melody. Watching him, I felt myself relax with him, both of us at one with the music. I laid back as he took the melody and accompanied his voice with chords. I paused when he paused, and when I played the closing few bars, he held on to the last note, and we ended together perfectly, as though we had rehearsed it.

When the final chord faded out, he opened his eyes and looked over at me with a smile that could light up a room. Then he said, “That was very, very nice, kid.”

At a loss for words, I said, “Well, thank you, Mr. Sinatra. I’m no Al Viola [Frank’s longtime guitarist], but I try.”

Frank turned to Jilly and started to laugh. “Al Viola? How the hell does this kid know Al Viola?” I was the wrong generation. The Ventures, yes. Al Viola, no.

Jilly responded by making a formal introduction. “Frank, this is my friend Tony Oppedisano. Tony O. Tony, Frank Sinatra.” He told Frank a little bit about me, and before I knew it, we were all chatting and laughing like we’d known each other for years.

Frank began teasing me about the tuxedo, so I said, “Well, you know, I’m really very Italian. When people pay me a compliment, especially a great one like you just did, my immediate reaction is, ‘Is the guy trying to give me malocchio?’ I know how to deal with that.” I opened my tux jacket to reveal the fire-engine-red lining.

Frank started roaring and said, “How old is this kid?”

It was the first of countless nights I would spend talking with Frank Sinatra. That first night, we played music, drank, and hung out until about six thirty, a respectable hour to call it a night, even for Frank. Usually, I’d realize I’d stayed out too late when I heard the garbage trucks beginning their rounds, and that morning, I heard them working right outside. It was like a signal to all of us. I packed up my guitar and amp, and we all made our way out to the curb together. It was daylight by then, and Frank’s limo was just pulling up. He was heading back to the Waldorf Towers.

Before I walked to my car, I said to him, “Mr. Sinatra, I’m not certain when I’ll have the good fortune to see you again, so I want to take the opportunity to wish you a very happy birthday. I know that today”—I looked at my watch and corrected myself—“rather, yesterday, was Sammy Davis’s birthday, and yours is coming up on the twelfth. So I want to wish you a happy birthday, Mr. Sinatra.”

Frank looked at Joe Petrone and said, laughing again, “Who is this kid?”

He reached out to shake my hand and said, “Let me tell you something. You’re a really talented guy. This business can be cruel. It can knock you down. It can kick your teeth in, but when it’s good, there’s nothing like it. So if you have the passion for it, hang in there. It will be good to you.”

Then he got into his limousine. It pulled away from the curb, and he disappeared from my view.

Very few people recognize the turning points in their lives until much later, if at all. I’m one of the exceptions. At four a.m. on December 9, 1972, in a club on Fifty-Second Street in New York, a page in my life story turned, and a new chapter began. As I walked back to my car that morning, barely feeling the pavement, I knew that my life would never be the same.