In college, I had a running debate with one of my sorority sisters: Who was the greatest singer of all time—Frank Sinatra or Andy Williams?

We now know who won that debate. Throughout Sinatra’s long career, other male singers were constantly nipping at his heels on the Billboard charts—Dick Haymes, Eddie Fisher, Perry Como, Dean Martin, and Bing Crosby, to name a few. And while some of those singers are better known than others, none comes close to matching Sinatra’s legacy. For generations past, present, and—it seems safe to say—-future, Sinatra remains The Voice.

James Kaplan’s biography, Frank: The Voice, pulls no punches in chronicling Sinatra’s rise as the first teen idol, his torrid and tortured love affair with Ava Gardner, his fall into near poverty and virtual obscurity, and his rise once again after winning an Academy Award. He never doubted his talents, but he frequently doubted himself, particularly concerning his relationships with women. Sinatra’s birth, requiring the use of forceps, left marks on his face, neck, and left ear. (Years later, he would insist on being photographed from the right). His mother, Dolly, deciding that one difficult pregnancy was enough, compensated by becoming a midwife, often performing abortions. Just under five feet tall, Dolly was a force, both inside the Sinatra home and within the “knockabout Italian streets of Hoboken.” In contrast, Sinatra’s father, Marty, was docile, leading to Frank’s lifelong search for male role models. (Since Dolly’s family was from Genoa, in northern Italy, Kaplan wonders about her decision to elope with Marty, whose family was from Sicily, looked down upon by Italians from the north).

Kaplan debunks many myths about Sinatra, beginning with his early childhood. He didn’t grow up poor. Thanks to Dolly’s ambitions and political maneuverings, the Sinatras kept moving up in neighborhoods and prestige. Frank enjoyed his own room and beautiful clothes. Dolly’s attention to her son, however, alternated between coddling him and abusing him. In the pre-Dr. Spock days, Dolly was not shy about doling out physical punishment with a small club and once pushed her son down a flight of stairs, knocking him unconscious. Yet, she was Frank’s fierce defender. In the early days of performing, Dolly would often make sure the right club hired him. Sinatra once told Shirley McLaine: “She scared the shit out of me. Never knew what she’d hate that I’d do.” Here we have the first clue behind Sinatra’s complicated relationships with women. “Sinatra would feel ambivalent about women until the end of his days,” Kaplan writes. “He would show every lover something of what Dolly had shown him.”

Like his mother, Sinatra was small in stature, only five feet seven and a half inches tall, but very thin, narrow in both the shoulders and hips. “Naked, Frank Sinatra was a fairly unexceptional specimen. Except.” Kaplan says the condition is called macrophallus, a medical condition that most men would happily suffer. Ava Gardner would later add to the legend, when asked why someone of her beauty would want Sinatra, a 119 pound weakling. “He may weigh only 119 pounds,” she shot back at the reporter, “but 19 pounds of it is cock.”

Millions of women who never had the pleasure were nonetheless seduced by Sinatra’s voice. The music world had never before witnessed such hysteria—bobby soxers lined up days in advance to get into his concerts. Kaplan says that some arenas began to smell of urine, young women refusing to give up their seats even to go to the bathroom. No one had ever managed to interpret lyrics with such meaning, such emotion. For a young generation, Sinatra’s yearning spoke to their hunger. He understood them and was able to reach them.

While Sinatra was able to touch hearts in a big arena, he had more trouble closer to home. After marrying his teenage sweetheart, Nancy Barbato, he would leave her for days, weeks, months, to go on the road, coming home long enough to create another child. They would have three—Nancy, Frank Jr., and Tina. Deep down, a product of his Catholic upbringing, Sinatra was reluctant to leave his marriage, even when he was essentially living with Ava Gardner. Finally, he did, but his two years with Gardner would prove to be a dark period of his life. His career was at a low point, his radio and TV shows canceled, his films, lackluster, and his recording career on hold. Gardner, on the other hand, was a rising star, shining in high profile films like Mogambo opposite Clark Gable and the Barefoot Contessa opposite Humphrey Bogart.

Then came From Here to Eternity. From the time he first picked up the novel by James Jones, Sinatra knew he was meant to play Maggio, a “dago” soldier from Brooklyn who ends up dying at the hands of Sgt. “Fatso” Judson played by Ernest Borgnine. Kaplan explodes the story told by Mario Puzo in The Godfather, where a singer who bears an uncanny resemblance to Sinatra (named Johnny Fontane in the book) wins a coveted movie role after the Mafia threatens the film’s producer. In reality, there was no horse head left in anyone’s bed. Rather, Sinatra lobbied relentlessly for the role, sending the producer and director endless telegrams signed “Maggio.” Initially, the studio preferred Eli Wallach for the part. Yet comparing the two screen tests side by side, Sinatra, thanks to his physical appearance and his Italian looks, was Maggio. Wallach’s unreasonable salary demands sealed the deal.

By the end of the book, Sinatra is on the rise again—holding an Oscar, recording what would become some of his best work with the inspired arrangements by Nelson Riddle, and enjoying a close relationship with his children. We know that there are still difficult times ahead, the breakup of his marriage to Ava, a third one to Mia Farrow that would also end in divorce. Allegations of ties to the Mafia, would dog Sinatra throughout his lifetime, leading to a snub by the young President Kennedy.

Controversy, suffering, angst were all part of the Sinatra DNA. Without those tortured feelings, perhaps his songs would not resonate like they do. Sinatra’s legacy continues to grow. Succeeding generations discover him. Other singers study his work, attempting to inject their own performances with something from The Voice. What that “something” is will continue to be debated. In the meantime, Kaplan has done an admirable job of helping us to understand this complicated genius.

For the Frank-o-phile on your gift list:

Frank: The Voice, by James Kaplan

From Here to Eternity, DVD, Frank’s Academy Award-winning performance

Frank Sinatra—Songs for Young Loves

Frank Sinatra—The Capitol Years, 3 CD set

Jolly Christmas from Frank Sinatra