Frank Sinatra. The name resonates like few others in the annals of entertainment. Ol’ Blue Eyes. The Chairman of the Board. The Voice. For decades, Sinatra Frank Sinatra captivated audiences worldwide, a towering figure whose talent was matched only by his complex, often contradictory, personality. He was the embodiment of cool, a master vocalist, a commanding actor, and a symbol of the fully emancipated male in postwar America. Yet, behind the suave public image resided a man of volatile moods, fierce loyalties, deep insecurities, and surprising vulnerability. Understanding the real Sinatra Frank Sinatra requires looking beyond the spotlight, into the shadows where anecdotes reveal the temper, the generosity, the power, and the loneliness of an American icon.
Drawing from intimate observations and extensive research gathered during the mid-1960s, a period when Sinatra was navigating career pressures, personal relationships, and the weight of his own legend, we can piece together a portrait of the man himself. This wasn’t just the singer on the stage or the actor on the screen; this was Sinatra Frank Sinatra dealing with a common cold that felt like a catastrophe, commanding loyalty from his inner circle, confronting strangers, cherishing family, and revealing glimpses of the kid from Hoboken who conquered the world but never fully escaped his own complexities.
The Temperament of a Titan: Moods and Confrontations
Frank Sinatra’s moods could shift as quickly as a musical key change, capable of plunging from jovial camaraderie to icy rage in moments. Even a common ailment like a cold could throw him into a state of “anguish, deep depression, panic, even rage,” as it threatened the uninsurable jewel: his voice. A Sinatra with a cold wasn’t just an inconvenience; it sent vibrations through his extensive network, affecting his staff, his friends, and his business ventures. His confidence, the bedrock of his persona, was intrinsically linked to his vocal cords.
This volatility wasn’t reserved for health scares. In a private Beverly Hills club in late 1965, Sinatra, nursing bourbon and a cigarette, stood brooding. His silence commanded the room; his companions knew better than to force conversation. Later, in the poolroom, his irritation found a target. Spotting writer Harlan Ellison wearing distinctive boots, Sinatra couldn’t resist.
“Hey,” he called out, his voice sharp. “Those Italian boots?”
“No,” Ellison replied.
“Spanish?”
“No.”
“Are they English boots?”
“Look, I donno, man,” Ellison retorted, turning away.
The room fell silent. Sinatra, with a slow, arrogant swagger, approached Ellison. “You expecting a storm?” he asked, a tricky smile playing on his lips.
“Look, is there any reason why you’re talking to me?” Ellison stood his ground.
“I don’t like the way you’re dressed,” Sinatra stated flatly.
“Hate to shake you up,” Ellison countered, “but I dress to suit myself.”
As tension mounted, Sinatra pressed, “What do you do?”
“I’m a plumber,” Ellison quipped. When corrected that Ellison wrote the screenplay for The Oscar, Sinatra dismissed it, “Oh, yeah, well I’ve seen it, and it’s a piece of crap.” Ellison pointed out the film hadn’t been released yet. “Well, I’ve seen it,” Sinatra repeated, “and it’s a piece of crap.” The confrontation, fueled perhaps by Sinatra’s own inner turmoil or boredom, ended only when Ellison left, adding another name to the long list of people who’d had unexpected, intense “scenes with Sinatra.” Moments later, Sinatra snapped at the assistant manager, “I don’t want anybody in here without coats and ties.” The incident, though brief, highlighted Sinatra’s capacity for public confrontation and intolerance when displeased.
His temper could also flare within his inner circle. An anecdote tells of him furiously throwing a bottle of catsup at one of his men, Ed Pucci, a former NFL lineman, simply for bringing him a frankfurter with the condiment he apparently abhorred. Despite the size and strength of the men around him, none would dare retaliate. He was the boss. Il Padrone.
Even his well-intentioned staff could trigger frustration. A casual observation that his jeep in Palm Springs needed painting snowballed through the ranks into an urgent command requiring an overnight crew at overtime rates. When the request for approval finally reached Sinatra, he was bewildered, confessing tiredly that he didn’t care when the jeep got painted. He remained a wholly unpredictable man.
Yet, this same man possessed a remarkable capacity for dramatic kindness. At a party hosted by Sinatra at his former wife Nancy Sr.’s home, a young reporter, Jane Hoag, accidentally knocked over and smashed one of a pair of valuable alabaster birds. As Sinatra’s daughter Nancy Jr. began to exclaim about its sentimental value, Sinatra cut her off with a glare. In the stunned silence, he walked over, deliberately flicked the matching bird off the table, smashing it, then put an arm around the mortified young woman and said gently, “That’s okay, kid.” It was a gesture of unexpected grace, instantly diffusing her embarrassment and showcasing his complex nature – capable of rage over catsup, yet grandly dismissive of valuable objects to protect someone’s feelings.
Il Padrone: Power, Loyalty, and the Inner Circle
Frank Sinatra commanded loyalty with an intensity that mirrored the Sicilian concept of uomini rispettati – men of respect. He expected “All the Way; All or Nothing at All” from his friends and associates. Easy Anglo-Saxon outs were not permitted. But for those who remained steadfastly loyal, Sinatra’s generosity knew no bounds. He showered them with fabulous gifts, personal kindnesses, unwavering support during downturns, and effusive praise during triumphs.
His inner circle comprised a diverse cast, united by their connection to the magnetic center. There was Leo Durocher, the legendary baseball manager, shooting pool nearby. Jim Mahoney, his press agent, impeccably dressed in expensive continental suits, navigated the complex world of Sinatra’s public image, fielding calls about controversial documentaries and managing press inquiries. Mahoney, powerfully built but soft-spoken, kept mementos of crises past – sleeping pills from the kidnapping of Frank Sinatra Jr., a replica of the ransom note – tangible reminders of the pressures surrounding his client.
Brad Dexter, a character actor whose life became intertwined with Sinatra’s after saving him from drowning in a riptide in Hawaii, served as a constant companion and producer in Sinatra’s film company. Big, broad-shouldered Dexter felt fiercely protective, confessing in a moment of self-revelation, “I’d kill for him.” This dramatic statement, while perhaps hyperbolic, captured the fierce fidelity Sinatra inspired. Dexter constantly scanned for potential trouble, knowing Sinatra’s presence could intoxicate a room, bringing out the best and worst in people, potentially leading to headlines if Sinatra’s mood turned sour.
Other key figures included Jilly Rizzo, owner of Sinatra’s favored New York saloon, Jilly’s on West Fifty-second Street, a place treated almost like a shrine by Sinatra admirers. Al Silvani, a boxing manager turned film company associate; Dominic Di Bona, his wardrobe man; Ed Pucci, the 300-pound aide-de-camp who endured the catsup incident – these were the paisanos, the men close to the boss.
The manuscript that Talese turned in to Esquire, showing meticulous planning. (Photo by Elon Green)
Observing Sinatra holding court at Jilly’s revealed a fascinating ritual. Dozens gathered outside, hoping for a glimpse. Inside, even close friends approached cautiously. A touch on the shoulder, a brief nod of recognition from Sinatra, a wave – these were signs of acknowledgment, after which they would retreat. They had “checked in,” paid their respects. Sinatra seemed to dwell simultaneously in two worlds: the jovial swinger entertaining showbiz pals like Sammy Davis Jr. or Liza Minnelli, and Il Padrone, the respected patriarch acknowledged by his loyal paisanos.
This power extended beyond personal relationships into the fabric of the entertainment industry and his vast business empire – a film company, record company, private airline, missile-parts firm, real estate holdings, and a personal staff of seventy-five. He seemed the embodiment of the fully emancipated male, doing exactly what he wanted, backed by money, energy, and an apparent lack of guilt. He set his own terms, even dictating working hours on film sets, famously preferring noon start times over the industry standard dawn calls. The power to decide when a film shoot began was, perhaps, the ultimate symbol of his influence.
His generosity was legendary, often intensely personal. When a musician friend lost his wife and home in a mudslide, Sinatra personally stepped in, finding him a new house, covering unpaid hospital bills, and meticulously overseeing the furnishing, right down to the silverware and linen. He personally selected dozens of Christmas gifts, remembering specific preferences for colors and sizes. Yet, this kindness existed alongside the potential for sudden, explosive anger. He was Sinatra. The boss. Il Padrone. And everyone knew it.
From Hoboken to Hollywood: Roots and Rise
Francis Albert Sinatra entered the world on December 12, 1915, in Hoboken, New Jersey, nearly dying at birth. A difficult delivery left permanent scars on the left side of his neck from a doctor’s forceps, marks he chose never to obscure. His father, Martin Sinatra, a Sicilian immigrant from Catania, was a quiet bantamweight boxer known as “Marty O’Brien” – adopting an Irish name was common for Italians navigating the Irish-dominated city structures of the time.
The driving force in the family was his mother, Natalina “Dolly” Garaventa. Brought from Genoa as an infant, Dolly was ambitious, energetic, and fiercely protective of her Italian heritage, known to swing her handbag at anyone uttering ethnic slurs. A skilled chocolate dipper offered a chance to train others in Paris, she instead focused on local power. By adeptly playing politics within North Jersey’s Democratic machine, Dolly became a formidable figure in Hoboken’s third ward, capable of delivering hundreds of votes. This influence secured Martin a position, and later a captaincy, in the Hoboken Fire Department – openings were “made” at her insistence.
Dolly had high hopes for her only child, initially dreaming he’d become an aviation engineer. Discovering his aspiration to be a singer like his idol, Bing Crosby, infuriated her initially – she threw a shoe at him. But realizing his determination (“he takes after me,” she’d later admit), she eventually encouraged his ambition. Despite recollections of a sometimes lonely childhood, Frank was never a slum kid. Always well-dressed, he earned the nickname “Slacksey O’Brien” for his abundance of trousers.
His generation of Italo-American boys often found their voice in song rather than words. While lacking prominent novelists compared to other ethnic groups, they excelled bel canto. Perry Como, Tony Bennett, Vic Damone – many aimed for stardom, but none saw it more clearly than Sinatra Frank Sinatra. He relentlessly pursued his goal, singing nightly at the Rustic Cabin for $25 a week, while also performing unpaid on New York radio for exposure.
His break came with the big bands. He joined Harry James’s orchestra in 1939, scoring his first hit, “All or Nothing at All.” Though fond of James and the band, Sinatra seized the opportunity to join Tommy Dorsey’s band, arguably the country’s best, for $125 a week. Dorsey knew how to showcase a vocalist, and Sinatra’s star ascended rapidly. Leaving James was wrenching; Sinatra recalled standing alone in the snow with his suitcase after the band bus departed, tears streaming as he watched the taillights disappear, hating to leave the band’s spirit behind.
But leave he did, as he would leave other comfortable situations, always seeking more, striving to achieve everything within a single generation. He fought under his own name, championing underdogs (espousing the Negro cause decades before it was fashionable) and sometimes terrorizing top dogs (reportedly throwing a tray of glasses at drummer Buddy Rich for playing too loud). He lived an immigrant’s wildest dream, giving away thousands in gold lighters before he turned thirty. He became a powerful voice against anti-Italian prejudice, vocally opposing stereotypical portrayals on shows like The Untouchables and resentful when figures like Joseph Valachi were elevated as Mafia experts.
His relationship with his parents remained central. Dolly, proud and powerful, claimed, “You cross him, he never forgets,” but also insisted, “He can’t make his mother do anything she doesn’t want to do.” Even in adulthood, she maintained influence, jesting that he still wore the brand of underwear she used to buy him. For their fiftieth anniversary, Sinatra gifted them a sixteen-room house in Fort Lee, New Jersey, a home filled with a curious mix of the sacred and the secular: photos of Popes alongside Ava Gardner and Dean Martin, statues of saints near autographed chairs and bottles of bourbon. Dolly remained a force, holding court in her kitchen, advising petitioners, and caring for Martin, whose boxing days had left him with a stiff arm. Weekly phone calls with her famous son continued, marked by affectionate sparring, like when she playfully dismissed his East Side Manhattan apartment as being in an “awful neighborhood.”
The Voice, The Fall, and The Comeback
Sinatra’s voice was his essence, the instrument that launched a million swoons and defined a generation. From his early days with Dorsey, where hits like “I’ll Never Smile Again” solidified his fame, he became “The Voice,” mesmerizing audiences at the Paramount Theatre, his bow ties and earnest delivery captivating legions of bobby-soxers.
But the pedestal was precarious. By the early 1950s, his career had plummeted. His records weren’t selling, his television show was a comedic misfire, and he recorded disastrous novelty songs like “Mama Will Bark.” His voice itself seemed to falter, and his artistic judgment waned. Public opinion turned; fans who once swooned now jeered. Many attributed his decline significantly to his tumultuous pursuit of movie queen Ava Gardner.
Ava was then at the peak of her fame, arguably one of the world’s most beautiful women. Sinatra was deeply smitten, but the relationship was fraught. Friends suggested Ava, insecure herself, couldn’t provide the constant adoration Sinatra craved, while she chafed at the constant presence of his entourage – a stark contrast to his first wife, Nancy Sr., the “good Italian wife” who would uncomplainingly make spaghetti for the entire band. Sinatra chased Ava across continents, neglecting his own career. His manager Hank Sanicola observed, “Ava loved Frank, but not the way he loved her. He needs a great deal of love… wants it twenty-four hours a day.” The power dynamic was reversed; Sinatra was down, and the woman on top couldn’t, or perhaps wouldn’t, lift him up. It was a hard lesson: when a proud man falls, a woman at the pinnacle may not be the one to help him rise.
Their marriage lasted barely two years, ending in divorce in 1953. Though Dolly reportedly tried to arrange a reconciliation, Sinatra, perhaps changed by the experience, was unwilling. He began to be seen with other women; the balance had irrevocably shifted.
Gay Talese planning the iconic Sinatra profile using his famous shirt-board method. (Photo by Elon Green)
Yet, even during this nadir, a deeper emotion began to infuse his singing. His recording of “I’m a Fool to Want You” from this period remains legendary. A friend recalled Sinatra recording it in a single, emotionally raw take, then immediately walking out of the studio. The pain, it seemed, fueled a new depth.
Somewhere amidst the wreckage of his career and marriage, a transformation occurred. The boyish singer began to evolve into a man. Flashes of the old talent resurfaced: a powerful recording of “Birth of the Blues,” acclaimed nightclub appearances. The industry was also shifting towards L.P.s, favoring artists with a concert style suited to longer formats.
The true turning point came with his role as Angelo Maggio in From Here to Eternity (1953). Winning the Academy Award for Best Supporting Actor marked a spectacular comeback. Fully recommitted to his talent, Sinatra Frank Sinatra reclaimed his throne. In 1954, Metronome named him “Singer of the Year,” and he unseated the reigning pop king, Eddie Fisher, in the U.P.I. disc-jockey poll. The man who had barked like a dog on a record was back, stronger, deeper, and more commanding than ever.
This comeback cemented his legendary status. He had everything, lost it, then clawed his way back, embodying resilience and defiance. He proved it was possible to uproot one’s life, break from the familiar, and rebuild on one’s own terms.
The Recording Studio: Sinatra’s Sacred Space
While Sinatra might treat movie sets with a certain playful irreverence, the recording studio was sacred ground. “Once you’re on that record singing, it’s you and you alone,” he explained. “If it’s bad and gets you criticized, it’s you who’s to blame… If it’s good, it’s also you. With a film it’s never like that… With a record, you’re it.”
His sessions were electric. Arriving at the studio, often seeming to dance across the sidewalk, he’d enter the intimate, airtight room, snap his fingers, and instantly command the space. Facing the orchestra, many of whom had played with him for decades, he dominated every musician, every instrument, every sound wave. These veteran players had accompanied him through countless renditions of songs like “You Make Me Feel So Young,” growing old alongside the timeless voice.
When Sinatra’s voice was “on,” the atmosphere became ecstatic. Excitement rippled through the orchestra and into the control booth, where friends like Dodgers pitcher Don Drysdale or golfer Bo Wininger, along with smiling women moving softly to the music, would wave encouragement from behind the glass. Sinatra, interacting playfully between takes (“Hey, Big D,” he’d call to Drysdale, “hey, baby!”), remained intensely focused during the actual recording.
The taping of his NBC television special, Sinatra – A Man and His Music, in November 1965 provided a stark example of how crucial his voice and his control were. Initially hampered by the lingering effects of his cold, Sinatra was tense and easily angered. Discovering the stage and orchestra platform weren’t arranged precisely as requested, he pounded a piano in his rehearsal room. Later, in the studio, his voice cracked on several numbers. When the director, Dwight Hemion, seemed unresponsive in the control booth, Sinatra’s frustration boiled over. “Why don’t we tape this mother?” he called out repeatedly. He lashed out at what he perceived as outdated production techniques.
After singing “Nancy,” a song inspired by his daughter, with unexpected warmth and power despite his condition, his voice faltered again. Watching a replay of the troubled taping, Sinatra quickly shut it down. “Forget it, just forget it,” he told Hemion. “You’re wasting your time. What you got there,” nodding at his image on the screen, “is a man with a cold.” He ordered the entire day’s work scrubbed, postponing taping until he recovered. The decision sent shockwaves through his staff and NBC, highlighting the immense pressure and financial stakes riding on his vocal health.
When taping resumed eight days later, the atmosphere was transformed. His cold gone, Sinatra was in fine voice, cracking jokes, unshakeable. When a camera accidentally hit a prop tree during a number, Sinatra calmly remarked, “We’ve had a slight accident,” and restarted the song flawlessly. He was back in control, the master of his domain.
After a successful session for his Moonlight Sinatra album, the respect and familiarity between Sinatra and his musicians were palpable. As they filed out, he knew them all by name, recalling details of their lives. He paused to chat with Vincent DeRosa, a French horn player from his radio days. Learning DeRosa’s daughter was now in college and had singing talent, Sinatra offered gentle, perhaps disappointing, advice: “Yes, but it’s very good for her to get her education first, Vicenzo.” It was a glimpse of the pragmatic gatekeeper beneath the charismatic performer, unwilling to become godfather to yet another aspiring talent, even the daughter of a loyal, long-time colleague.
Love, Loss, and Loneliness
Frank Sinatra’s relationships with women were as complex and publicized as his career. He married his neighborhood sweetheart, Nancy Barbato, in 1939. She was the plasterer’s daughter from Jersey City, the cornerstone of his early family life. They had three children: Nancy, Frank Jr., and Tina. Nancy Sr., described as a striking woman who never remarried (“When you’ve been married to Frank Sinatra…” she reportedly explained), maintained a respectful and affectionate relationship with him long after their divorce in 1951. Sinatra remained welcome in her magnificent Los Angeles home, sometimes wandering in, stoking the fire, and falling asleep on the sofa – a habit learned from years on bumpy band buses, and perhaps one of the few places he could find unguarded privacy.
His eldest daughter, Nancy Jr., held a unique place in his life. She was old enough to remember him as a father before the marriage broke up and witnessed his subsequent high-profile relationships with Ava Gardner, Juliet Prowse, Mia Farrow, and others. She even went on double dates with him. Yet, their bond remained strong. He called her daily, wherever he was in the world. The song “Nancy (With the Laughing Face),” inspired by her, consistently brought out a palpable tenderness in his performances. It was said she understood him better than anyone, the only person before whom he could be unashamedly himself. He wept on her wedding day. Despite his fame and complex life, he tried, as Nancy Jr. put it, to be “like everyone else,” sentimental and sensitive beneath the tough exterior. Yet, even she recognized the toll of his fame, realizing the sofa naps she once resented represented a rare escape from the constant scrutiny his famous face attracted.
His marriage to Ava Gardner was a firestorm, passionate and destructive. While it coincided with his career decline, it also seemed to forge a new resilience in him. After their divorce, the power dynamic shifted; he was no longer the one chasing.
His relationship with Mia Farrow in 1965, then just twenty years old, generated intense publicity and, according to observers, personal tiredness for the nearly fifty-year-old Sinatra. He seemed weary of the attention surrounding their dating.
Despite the glamour and string of famous companions, a current of loneliness ran beneath the surface. There were nights when, finding himself alone and not by choice after dialing multiple unavailable women, he would call his valet, George Jacobs. “I’ll be coming home for dinner tonight, George.” “How many?” Jacobs would ask. “Just myself,” Sinatra would reply, requesting something light. After Jacobs served him, Sinatra would dismiss him, never asking him to stay for company or cards, preferring solitude even when companionship was readily available.
This paradox – the man who craved adoration, commanded entourages, yet sometimes chose solitude – was central to his being. Dining late at night in Las Vegas or New York, surrounded by his trusted circle at a reserved table, felt like the closest approximation to the home life he’d left behind. He filled the homes of Nancy Sr. and Nancy Jr. with his furniture, tangible extensions of himself. He remained connected, yet fundamentally apart. As Nancy Jr. observed, “He is calm on the outside — inwardly a million things are happening to him.” Brad Dexter saw “an insatiable desire to live every moment to its fullest because… right around the corner is extinction.” Even Sinatra himself acknowledged the coping mechanisms, famously stating: “I’m for anything that gets you through the night, be it prayer, tranquilizers or a bottle of Jack Daniel.”
The Enduring Enigma
By late 1965, Sinatra Frank Sinatra stood at a unique precipice. He was nearing fifty, a milestone that seemed irrelevant to his enduring appeal. He was a prewar product who had defied the changing tides of popular culture, surviving and thriving in an era increasingly dominated by the young. He was the champ who made the comeback, a symbol of resilience. Men admired him, perhaps even envied his apparent freedom from domesticity and compunction. He made old men feel young, proving that vitality and relevance weren’t solely the domain of youth.
He remained meticulously presented – the conservative suits with flamboyant linings, the perfectly shined shoes, the convincing black hairpiece (one of sixty, cared for by a dedicated stylist). His clear blue eyes could instantly shift from warmth to icy anger to detached observation. He controlled menus in Italian restaurants, commanded stages in Las Vegas, and held court wherever he went, trailing his “neighborhood” of loyalists with him.
He couldn’t escape the constant observation. Driving his Ghia through Los Angeles, a young woman stares at the curb – It looks like him, but is it? Sinatra, catching her gaze, turns, meets her eyes, waits for the inevitable flash of recognition, smiles, and drives on. It was a daily occurrence, a small moment reflecting the inescapable reality of being Sinatra Frank Sinatra.
He was, and remains, a piece of the past, yet timeless. A man of immense talent, power, and charisma, yet plagued by insecurities and a volatile temper. Generous to a fault, yet capable of cutting remarks and fierce demands. He sought connection but guarded his privacy. He built an empire but seemed most himself in the controlled environment of a recording studio or surrounded by his chosen few. He was the ultimate paradox: the Chairman of the Board who sometimes felt like a lonely boy from Hoboken, the Voice of a century who struggled with a common cold, the icon who remained, until the very end, profoundly, complexly human. His life, like his music, contained multitudes – the highs, the lows, the swing, the sorrow, the unforgettable voice echoing through it all.
