“Being an 18-karat manic-depressive,” Frank Sinatra once said, “and having lived a life of violent emotional contradictions, I have an over acute capacity for sadness as well as emotion.”

He wasn’t kidding. Sinatra was far more than the most influential singer of the 20^th century and the Oscar winning star of films including From Here to Eternity, The Manchurian Candidate, On the Town and Guys and Dolls. He inspired outsized emotion not only in fans, but in other 20^th century celebrities, whose respective autobiographies are not complete without a story of Sinatra’s enormous, at times foolish, generosity (going so far as to try and score heroin for a desperate Billie Holiday as she was dying), terrific talent, or, according to Shelley Winters, his terrifying temper.

“Sinatra is a unique man, utterly without hypocrisy,” his friend Cary Grant noted. “It’s unusual for most people, and almost frightening to some, to be faced with honesty.”

His naked need to love and be loved also made Sinatra one of the era’s most prolific lotharios. Conquests both alleged and factual include his immortal beloved Ava Gardner, Mia Farrow, Marlene Dietrich, Gloria Vanderbilt, Lana Turner, Angie Dickinson, Marilyn Maxwell, Marilyn Monroe, Judy Garland, Jill St. John, Lauren Bacall, and most disturbingly, a fifteen-year-old Natalie Wood. Of course, there could have been another reason the ladies loved him. “There’s only ten pounds of Frank,” Gardner told reporters, “but there’s a hundred and ten pounds of cock.”

Dozens upon dozens of biographies have been written about Sinatra, none more exhaustive than James Kaplan’s masterful two-volume opus: 2010’s Frank: The Voice (802 pages) and 2015’s Sinatra: The Chairman (992 pages). Though Kaplan’s works are a masterclass in research and technical skill, the memoirs of those who actually knew the man behind the enigma—his daughters, Nancy and Tina; his fourth wife, Barbara; and his longtime valet, George Jacobs—which give a fuller sense of him. In their telling, Sinatra was a loveable man whose magnetism meant he was never physically alone, but who was entrapped in a narcissistic loneliness he could never escape.

“I think my dad desperately wanted to do the best he could for the people he loved,” Tina Sinatra writes in her insightful, searing memoir My Father’s Daughter. “But ultimately he would do what he needed to do for himself.”

Mama’s Best Boy

“She was a pisser,” Sinatra once confided in honorary Rat Packer Shirley MacLaine about his mother Dolly. “She scared the shit out of me.”

The two had been locked in a fight for survival since Francis Albert Sinatra was born on Dec. 12, 1915, in the Little Italy section of Hoboken, New Jersey. The 13 ½ pound baby had nearly killed the diminutive Dolly, and Francis also barely survived. The doctor ripped his face, neck and ears with forceps, leaving lifelong scars.

Dolly—and her son—would not be licked. A cursing, sometimes violent, rough-and-ready Democratic operator, suffragette, and occasional abortionist, Dolly completely overshadowed her husband: Marty, a former boxer and loveable lug. The Sinatras owned a mob-connected bar, propping precocious Frank on the piano to sing, until Dolly pulled strings to get Marty a more upwardly mobile job as a firefighter.

Frank was their only child—a hypersensitive, artistic, lonely boy in a time of big families, who was both spoiled and neglected. According to a sympathetic Kaplan, Sinatra would pay other boys to be friends with him, and he would listen to Bing Crosby records on repeat. As pugnacious and ambitious as his mother, he set his heart on being a singer, and Dolly used all her contacts to secure him gigs at local clubs. She also tried to protect him from his already strong libido (when Sinatra was arrested in 1938 on a morals charge, Dolly threw the woman who filed the complaint into her basement).

But Dolly needn’t have worried. Her son’s talent was innate, and one day while working as a singing waiter at a club called the Rustic Cabin, famed bandleader Harry James took notice. “This very thin guy with swept-back greasy hair had been waiting tables,” bandleader Harry James recalled, per Kaplan. “Suddenly he took off his apron and climbed onto the stage. He’d sung only eight bars when I felt the hairs on the back of my neck rising. I knew he was destined to be a great vocalist.”

Little Big Man

After career-making stints with James and Tommy Dorsey, Sinatra went solo, becoming a bobbysoxers’ idol after a run at New York’s Paramount Theater in 1942.

“It was a tremendous roar,” Sinatra later recalled. “Five thousand kids, stamping, yelling, screaming, applauding. I was scared stiff…Benny Goodman froze too. He was so scared he turned around, looked at the audience and said, ‘what the hell was that?” I burst out laughing.”

Dubbed “Swoonatra,” Sinatra was swept into a world of movie contracts, radio shows, constant partying with a posse of hangers-on, and all the women he could handle. While a besotted Kaplan seems to make one too many excuses for Sinatra (what was a young, virile genius to do?), he is also unflinchingly honest about his subject’s cocky recklessness, cruel jokes, menacing aura, and violent tendencies (including beating columnist Lee Mortimer outside Ciro’s, while screaming “I’ll kill you!”). His temper led his cronies to nickname him “the monster.”

But Sinatra met his match in screen siren Ava Gardner, whom Kaplan misogynistically refers to as the “most dangerous of creatures, a gorgeous nihilist.” By the late ‘40s, Sinatra’s career was on a downswing. He had spent all his money, and his torrid affair and subsequent marriage to Gardner would lead him to brawls, booze, pills, and suicide attempts—some done out of despair, some in an attempt to manipulatively lure her back to him. The romance titillated the public, but utterly exhausted their friends.

“We would be sitting in the living room and hear them upstairs in the bedroom quarreling and arguing,” one insider told Kaplan. “Ava would scream at Frank and he would slam the door and storm downstairs. Minutes later we’d smell a very sweet fragrance…Ava had decided she wasn’t mad anymore, and so she sprayed the stairwell with her perfume. Frank would smell it and race back up to the bedroom. Then it would be hours before he’d come back down.”

Daddy’s Girls

It is astounding to comprehend that throughout much of this madness, Sinatra had a wife and three children pining for him at home.

He had married Jersey girl Nancy Barbato in 1939, when he was still just a struggling crooner. In all the biographies, Nancy comes out as a gem: caring, classy, motherly and nobody’s fool. (According to Tina, she would abort one child during a particularly brutal part of their marriage.) The couple had three children—Nancy, Frank Jr., and baby Tina.

While both Tina’s memoir, 2000’s My Father’s Daughter, and the younger Nancy’s 1985 celebratory Frank Sinatra, My Father are deeply protective, prideful and kind, there are many differences between the two books. Nancy’s—which was released when Sinatra was still alive—presents him almost worshipfully, as a wise (if often absent) and supportive Italian-American patriarch.

Tina’s view is more nuanced and clear-sighted. As Sinatra’s “most demanding child,” she admits to being deeply wounded by his frequent absences, which continued after he and Nancy divorced in 1951. “My father was a man of contradiction,” she writes. “He wanted to be consistent, but his spirit was fractured.”

According to both Nancy and Tina, Sinatra was a confidant who spoiled them rotten at their big Christmas gatherings at his estate in Palm Springs. He also cooked delicious Italian meals for them, and held them when they were crying. “It was a lot to miss, our father’s physical presence,” Tina writes. “Dad was like a campfire, the point where we gathered and felt warm. He had such a big presence—he put out this tremendous energy, and we all felt more alive around him.”

He would return often, looking to his “sweetheart” Nancy Sr. for comfort and support. (The two even had a brief rekindled romance in the 1970s.) If a child’s love is the measure of a man, there must have been something special about Sinatra. “Ohhh,” he once told his daughter Nancy as she gave him a big hug. “I’d turn my world upside down for you.”

Mobs R Us

If his children saw the cuddly side of Sinatra, George Jacobs was in the middle of his non-stop, ring-a-ding adult world. 2009’s Mr. S: My Life with Frank Sinatra is a gossipy, scandalous, deliciously dirty account of his boss’s life from Sinatra’s comeback in 1953, when he won the Oscar for From Here to Eternity, until he cruelly dumped Jacobs in 1968, for daring to dance with his then-wife Mia Farrow at a Los Angeles club.

As Jacobs notes, Sinatra was in awe of tough guys, be they on-screen pretenders like Humphrey Bogart or the real deal. Sinatra had known and befriended mobsters since his youth, leading to a massive FBI file. There were stories of mysterious beatings, threats, even a deadly car crash. Bad things seemed to happen to people who crossed Sinatra, and his less savory associates were often suspected.

The singer was particularly awed by the brutal Chicago mob boss Sam Giancana. When Giancana visited Sinatra at his home in Palm Springs, Jacobs watched as his boss meekly followed the mobster around the golf course, as Giancana lectured him on the casino business.

Sinatra, Kaplan claims, was also enamored by power in its more official forms. A progressive liberal who had made brave stances against racism since the beginning of his career, Sinatra was drawn into the world of the Kennedys through his friendship with the hapless Peter Lawford and his wife Pat Kennedy. Not only was he inspired by John Kennedy as a candidate, but he was also blown away by the family’s elegance. After all, Jacobs writes, Sinatra “craved class like a junkie craves the needle.”

According to both Kaplan and Tina Sinatra, his two worlds collided when Joe Kennedy Sr. cryptically asked for help securing votes for John Kennedy in the West Virginia primaries from mob-infested unions. Sinatra asked Giancana for assistance, and low and behold, Kennedy won. Kennedy would also win a suspicious number of votes in Giancana-controlled Chicago during the general election. Sinatra also worked tirelessly on courting other entertainers' support and went out on the campaign trail. “Ye assholes of little faith,” a relieved Sinatra said to his skeptical friends on election night.

The Kennedys would use (and then carefully discard) Sinatra in other ways as time went by. On a visit to Sinatra’s Palm Spring estate, John Kennedy asked Jacobs what he wanted as a Black man in America. Jacobs turned the tables, asking, “What do you want, Jack?”

“I want to fuck every woman in Hollywood,” the future President of the United States allegedly replied.

The Summit

By 1960, Frank Sinatra was truly the “Chairman of the Board” and at the pinnacle of American pop culture. Production started in Las Vegas on the Sinatra produced Ocean’s Eleven, starring Sinatra, his devoted mentee Sammy Davis Jr., Dean Martin, Peter Lawford and Joey Bishop. The five men called themselves “the summit.” Only later would they be immortalized as “the rat pack,” a name Sinatra hated.

By night, they appeared onstage at the Sands Casino, singing, cutting up, drinking, taking steam baths after the show, surrounded by showgirls and sex workers. By day, they shot a movie on the fly, befitting Sinatra’s reputation as a “one take Charlie.” As Kaplan notes, Sinatra was their undisputed leader. One late morning, co-star Norman Fell supposedly looked out his casino hotel room’s window to see Martin, Lawford and Davis running past the pool. “Fell stuck his head out and yelled, ‘Hey, where are you guys going?’” Kaplan writes. “And Sammy said, ‘Frank’s up!’”

But over the years that they performed together (minus Lawford and Joey Bishop who were both eventually banished by Sinatra for supposed acts of betrayal) even the often-fractious Rat Pack could not keep up with Sinatra’s insatiable need to party, to be awake, to be stimulated. One day, when Sinatra complained about being bored on a 40-minute helicopter ride, Martin decided to make the next ride more interesting by buying two guns.

“When we got on the helicopter…I gave him one, a loaded .22,” Dean recalls in Frank Sinatra, My Father. “And time just flew by, he was shooting at anything, dust, as long as he had something to do. I started shooting across his face. He said, ‘You’re a little close there, dago.’ Hell, I did not want him to be bored, right?”

The Autumn Leaves

After Sinatra’s ill-fated marriage to the much younger Mia Farrow ended in divorce in 1968, times were changing, and Sinatra was not in the groove. In 1971, he announced he was retiring. At a star-studded final performance at a benefit for The Motion Picture Relief Fund, a tearful Rosalind Russell introduced her pal for what seemed to be the last time.

But Sinatra was soon back onstage, unable to stay away from his craft and the crowds. At this point Kaplan seems to lose interest in Sinatra, who became increasingly conservative, befriending the Reagans (whom he had once despised). In 1976, he married enterprising former showgirl Barbara Marx, whom Kaplan, Tina and Nancy all seem to dislike. So did Sinatra’s mother. “I don’t want no whore coming into this family!” she exclaimed at one point, according to Tina.

But Dolly was soon out of the picture. She was killed in a plane crash in 1977, shattering her only son. Though Kaplan accused her of isolating and manipulating an often brooding, confused Sinatra, Marx’s memoir, Lady Blue Eyes, paints a picture of a rather likable, materialistic, clear-eyed showbiz survivor who knew exactly what she was giving up—and getting—by marrying Sinatra. “It probably took another year before I grew accustomed to the idea that I now carried his iconic name,” Marx writes. “At first, I’d almost whisper when booking a restaurant reservation or beauty parlor appointment. Even to say ‘Mrs. Sinatra’ out loud felt like bragging.”

There were still good things ahead for Sinatra: heartfelt philanthropy, happy moments as a grandfather. But there were also battles within the family over money, endless embarrassing tours where Sinatra’s great voice abandoned him, and hours spent with a bottle of Jack Daniels (according to Barbara he rarely drank water because “fish fuck it”). When an ailing Sinatra finally died in 1998, Tina came to see it as a tender mercy. “He could never be at peace, never stop running, until he stopped,” she writes. “My father did not die. He escaped.”