Few names in American pop culture are as universally adored as Frank Sinatra. His persona was larger than life. His life, even, was larger than life. Charismatic. Suave. Oscar-winning actor. Friend to presidents. The speculative—yet convincing—mob ties that somehow enriched his legacy rather than add rancor. And, of course, there was that unmistakeable croon. The catalyst for such nicknames as “Swoonatra” and “The Voice.” The irascible and esteemed music critic, Robert Christgau, called him the greatest singer of the 20th century. And who could convincingly argue with that claim? Listening to Sinatra is like funneling Christmas through a voicebox. This past Monday would have been his 101st birthday, and as we find ourselves on the eve of the holidays, we remember Frank Sinatra.
Sinatra was born in 1915 in Hoboken, New Jersey to a midwife and a boxer, both Italian immigrants. He grew up fascinated by music and, despite never formally learning to read it, he worked very hard to understand it. His reverence for Bing Crosby led to a love affair with Big Band jazz. After a teenage introduction to the genre with a troupe called the Hoboken Four (they were the 3 Flashes before Sinatra joined), the budding singer watched his star rise higher and higher; or, rather, he gave it a mighty shove into the night sky.
Through hard work and a resounding voice that belied his thin frame, Sinatra thrust himself onto the scene, bouncing around with Big Band bandleaders like Harry James and Tommy Dorsey. With the latter, Sinatra was eventually engaged in ugly contractual issues that, rumor has it, were settled by the mafia. As the story goes, his gangster godfather, Willie Moretti, bribed Dorsey with a few thousand dollars and a gun to his head in order to force him to release Sinatra from his contract. By the time he went solo—reportedly because of an insatiable desire to compete with Crosby—the crooner had already lived a colorful life. Now he was about to be a star.
In 1942, Sinatra opened at New York’s Paramount Theater, marking the official arrival of Sinatramania, a precursor to the manias that would later accompany stars like Elvis and The Beatles. The performance was a smash. Within a few weeks of the show, more than 1,000 Frank Sinatra fan clubs were registered.
George Evans, the singer’s publicist, painted Sinatra as a vulnerable Italian-American who emerged triumphant from a rough childhood. It was an image both endearing and enduring, and Sinatra rode that image and that velvet croon to towering fame. By the end of 1945, a poll in Down Beat magazine listed him as the most popular male vocalist, placing him ahead of  both his erstwhile idol, Bing Crosby, and everyone else in the world. His debut album, The Voice of Frank Sinatra, mirrored his meteoric rise, climbing to No. 1 on the Billboard chart soon after it was released in 1946. But no one, not even Ol’ Blue Eyes, can stay at the top forever.
In the early ’50s, Sinatra sank to a nadir, both in his career and in his life. An extramarital affair with actress Ava Gardner ruined his first marriage with Nancy, with whom he had three children. Evans, a close friend, died unexpectedly. Financial troubles forced him to borrow $200,000 from Columbia Records to pay back taxes. By 1952, he was playing the Kauai County Fair in Hawaii. Soon thereafter, Sinatra was dismissed from Columbia altogether. This wasn’t the end, though, of course; Sinatra packed his bags for Las Vegas, the refuge for stalled careers, and began rebuilding his star.
Once on the strip, the crooner became part of the illustrious vocal supergroup, The Rat Pack, which featured, among others, Dean Martin and Sammy Davis Jr. Sinatra then buried himself in work. He appeared in the 1953 film, From Here to Eternity, winning an Oscar for Best Supporting Actor, and he signed a lucrative contract with Capitol Records the same year. After recording and listening to playbacks of, “I’ve Got the World on a String,” his first song with Capitol, he famously exclaimed: “I’m back, baby, I’m back!”
A slew of critically acclaimed releases followed in both film—The Man with the Golden Arm (1955), The Manchurian Candidate (1962)—and music: Songs for Young Lovers (1954), In the Wee Small Hours (1955), Songs for Swingin’ Lovers! (1956), Come Fly With Me (1958), Come Dance With Me (1959). He wouldn’t peak, though, until ’65. That year, a Rat Pack benefit concert was broadcast live into movie theaters. His latest record, September of My Years, won the Album of the Year Grammy, and one of its singles, the appropriately titled, “It Was a Very Good Year,” won for Best Vocal Performance by a Male. In November, just before his 50th birthday, he released a career anthology, A Man and His Music. It would win Album of the Year in 1966.
Over the next couple decades, Sinatra maintained his prolific output, collaborating with a bevy of luminaries and cementing his legacy as music magnate. There was Sammy Davis Jr. and Dean Martin, of course, as well as Nat King Cole, Quincy Jones, Count Basie, Bing Crosby, Antonio Carlos Jobim, Gracy Kelly, Sarah Vaughan, Ella Fitzgerald, John Denver, Luciano Pavorotti, and, on-screen, Doris Day, Rita Hayworth, and Faye Dunaway. He was nominated for multiple Oscars and even covered a number of pop hits in order to remain contemporary: Elvis’s “Love Me Tender,” Paul Simon‘s “Mrs. Robinson,” and The Beatles’ “Something,” a track Sinatra called “the greatest love song of the past 50 years.†When all was said and done, Sinatra left us with more than 1,000 recordings.
It’s the narratives in between the art, though, that persist as Sinatra’s most captivating. The singer befriended and campaigned for both JFK and Reagan. He was married to both Ava Gardner and Mia Farrow, and he reportedly ended engagements with Lauren Bacall and Juliet Prowse. He had fights with notable journalists he felt had crossed him. And he was friends with gangsters like Sam Giancana and Lucky Luciano, with whom he attended the Mafia’s legendary Havana Conference in 1946. He also played an active role in desegregating hotels and casinos (though he did make occasional racist jibes to Davis Jr. during performances). And for all of it he was impeccably groomed. As the best, he felt that he owed the best to his fans, so he dressed to the nines—an outward expression of the assiduous man beneath the suit.
Frank Sinatra died of a heart attack in 1998 at the age of 82. The lights on the Las Vegas strip were dimmed and casinos stopped spinning to observe a moment of silence. The Empire State Building turned its lights blue in his honor. And his gravestone was branded with the words, “The Best is Yet to Come,” the name of a 1959 song composed by Cy Coleman and intimately associated with Sinatra. Though he didn’t compose his own material, Ol’ Blues Eyes brought it to life with a singular showmanship, poise, and vibrance. His hard work got him to the show. His candor won him the world’s adoration. And his voice brought him immortality. Today we still venerate that voice, and we still hope that the best is yet to come.
