One hundred years after his birth, the man is gone, but his miraculous voice remains. His legend looms just as large, and his eyes, twinkling at us from below the rim of a snappy fedora on the cover of any number of albums, are just as blue.
“Few American vocalists have had the impact of Frank Sinatra on our pop culture,” said J. Randy Taraborrelli, author of Sinatra: Behind the Legend (Grand Central Publishing, 2015). “He’s of a time when great singers were America’s special pride. No one has ever come close to his ability to deliver a song and impart to the listener the full emotion of that tune.”
Making his “debut” in 1915 in Hoboken, New Jersey, the son of Italian immigrants, Sinatra almost died before he was born—doctors struggled to get the enormous 13½-pound baby out of his mother, who was less than five feet tall, according to his official website. It would not be the first time that Sinatra beat the odds and recovered from what might have been a terrible defeat.
It was Sinatra’s mother who got Frank his first musical gig after the boy was expelled from high school for bad behavior. His mother got him into a musical group, turning the Three Flashes into the Hoboken Four. In 1939, Frank cut a demo record of the song “Our Love,” and a few months later he signed on with the Harry James Band. Later that year, Frank joined the Tommy Dorsey Orchestra before becoming a successful solo artist and an idol of the “bobby sox” crowd in the early 1940s.
Sinatra’s life was marked by the same kind of impeccable timing that would become the hallmark of his unmistakable pacing and phrasing as singer. Coming of age as a performer at the height of the radio era, Sinatra released his first album, The Voice of Frank Sinatra, in 1946. By the early 1950s, his career had stalled, and Frank would jump-start it by conquering another uniquely 20th-century medium: film. After winning an Academy Award for Best Supporting Actor for his role in From Here to Eternity, Sinatra released a string of legendary albums, including In the Wee Small Hours, Songs for Swingin’ Lovers!, Come Fly with Me and Nice and Easy. The bobby-sox hero had grown up and his music had grown up with him.
By the 1960s, Sinatra was the kind of multimedia superstar never before seen in popular culture. He cavorted before audiences with his Rat Pack friends in Las Vegas, racked up one hit movie after another in Hollywood, and rubbed shoulders with President John F. Kennedy in Washington, D.C.
Meanwhile, Sinatra’s personal live became the stuff of tabloid fodder that would have burned up the Internet if it had happened in the next century. “While this made for a wild ride, it also made for a man who was unpredictable in his moods and, thus, not someone any of his women considered the ideal mate,” said Taraborrelli. Sinatra was married four times; three of those marriages would end in ugly and public divorces. He was prone to mood swings and bouts of severe depression. He was often linked to organized crime, and his son, Frank Sinatra, Jr., was the victim of a bizarre kidnapping plot in 1963.
Still, through all the personal turmoil, through subsequent retirements and comebacks, there was the music, a patented blend of love, soul, heartbreak and machismo that could never be duplicated. It was the music of parents, and then of grandparents, and then of subsequent fans who would discover it in the wee small hours of their own lives—when their world seem to boil down to a broken heart, a tumbler of booze, and a sympathetic pal who could put “that old ennui” to music so perfectly.
Frank Sinatra’s life is the life that the American Dream dreams about, the standard by which the terms “superstar” and “legend” are measured. “I always think of Frank as a man for whom excess was never enough,” said Taraborrelli. “He lived his life full throttle, never satisfied with the status quo. Maybe to his credit—or maybe not, depending on one’s view of things—he always wanted more, was always looking for the next big conquest, both personally and professionally, and he was sure that, as his song says, “the best” was always “yet to come.”
To celebrate Sinatra’s 100th, here is a playlist of five of his best songs.