The Tragic Real-Life Story Of Frank Sinatra

When people remember Frank Sinatra, they remember a musical legend — Ol' Blue Eyes, the Chairman of the Board, the Rat Pack, a singer who revolutionized music in the 20th century. He's inspired generations of musicians who try to capture just a hint of the charm, charisma, and style that Sinatra naturally exuded. After his death in 1998, President Bill Clinton (per Rolling Stone) spoke on behalf of the nation's mourners, "I think every American would have to smile and say he really did it his way.'"

However, for all of the reverence he's received and for all of his everlasting popularity, it's hard for most to realize just how complicated and gut-wrenching life could be for a man who seemingly had it all. Frank Sinatra will always be immortal to those who hear his music, but from his struggles with mental illness to his crushing loneliness to his desperation for true love, few realize just how painfully human Ol' Blue Eyes was.

In spite of his talent, Frank Sinatra actually had to grapple with loneliness in childhood. Frank was the only child of Italian immigrants who were both very active and prominent in their Hoboken neighborhood. His father, Antonino Martino, or "Marty," owned a local tavern and was a part-time prizefighter. Frank's mother, Natalina, or Dolly, was a midwife and, according to The Irish Times, also helped desperate women to obtain illegal abortions. Dolly was also involved in local politics and was elected Democratic Ward Leader in their neighborhood.

His parents' work and activities meant they were often away, so young Frank was usually left on his own or with his grandmother. Most children in Frank's predominantly Italian neighborhood came from large families, while he grew up an only child, which was considered highly unusual. According to VQR, in a later interview with journalist Pete Hamill, Sinatra admitted that he longed for a sibling when he was a child: "I used to wish I had an older brother that could help me when I needed him. I wished I had a younger sister I could protect."

Bing Crosby was Frank Sinatra's greatest inspiration for becoming a professional singer. A huge fan of the celebrity crooner, the teenage Frank had a picture of Crosby hanging in his bedroom. Crosby's warm, passionate, but laid-back singing technique was the foundation that Frank built on until he could develop his own unique style. Frank even met his idol briefly in 1935 at a Newark Club, but they wouldn't meet again for nearly a decade — when Frank was a huge star in his own right.

According to JAZZIZ, by the time the 1940s rolled around, Crosby was still popular, but Sinatra's fame was skyrocketing. Bing had fans, but he was never greeted by hoards of screaming, swooning teenage bobby soxer girls that made up Sinatra's fanbase — although, PBS NewsHour reports that during his early career days, Sinatra's publicist paid teenage girls $5 each to shriek to whip up enthusiasm for the singer. Crosby took Frank's rising popularity in stride, saying that Sinatra was a singer that comes around once in a lifetime — then jokingly adding, "but why did it have to be my lifetime?"

After that, a media-driven rivalry was born. The two competing crooners would frequently trade barbs and insults at each other on public radio broadcasts. The rivalry was played up for media attention, but it was never serious. Later, the two would perform duets together and co-star in movies such as High Society.

Although he always refuted it, Frank Sinatra absolutely had ties to the mob. According to History, Sinatra's FBI profile reads like a complete guidebook to the Mafia. Sinatra was known to be good friends with the infamous Chicago mob boss Sam Giancana and his crew. He outwardly socialized with the Fischetti Brothers, Joseph and Charles, who were known to conduct illegal gambling operations. He blatantly partied with Detroit mobsters Anthony and Vito Giacalone. If Sinatra ever needed to get out of a contract or was simply ticked off about a perceived insult, someone could expect to get a visit from a couple of goons — visits that might or might not end with violence. In return, Frank would often perform a few shows as favors for his mob buddies.

For all of Sinatra's denials of Mafia ties, he didn't do much to conceal who his friends were or his participation in their shared activities — gambling, women, and money. The FBI kept a close eye on Sinatra, but he was never charged criminally for his mob-related activities or associations. Sinatra's full FBI record was not released until after his death.

Despite his warm and romantic voice, Frank Sinatra was known to have an extremely short fuse. According to GQ, during a show in Hong Kong, a missed light cue prompted him to destroy his dressing room and his hotel suite, breaking priceless antiques during the tantrum. Another time, while in a drunken rage, he drove a golf cart through a shopping mall window. J. Randy Taraborrelli's biography Sinatra: Behind the Legend details how the singer once threw a plate of pasta at the wall in an Italian restaurant because he deemed the pasta too soggy.

Referenced in The New Yorker's review of James Kaplan's biography of Frank Sinatra, Ol' Blue Eyes also had a habit of bullying venue employees and less famous entertainers and getting his mob friends to beat up people he didn't like. He seemed to have a particular dislike of stand-up comedians, likely due to his personal insecurities and fears of being publicly humiliated. Comic Shecky Greene made a remark that angered Sinatra, and Greene was soon mobbed by a group of Sinatra's friends. Comedian Jackie Mason made a series of jokes about the much older Frank Sinatra's marriage to 21-year-old Mia Farrow, which resulted in anonymous death threats. According to Vanity Fair, when Mason refused to stop making Frank Sinatra jokes, shots were fired into his hotel room. He later had his nose and cheekbones broken by a complete stranger.

Most would think a celebrity like Ol' Blue Eyes would have very little to be depressed about. He seemed to have it all — talent, money, success with women, and influence. However, Sinatra was known to suffer from extreme depressive episodes. If he was alive today, he'd probably have been diagnosed with bipolar disorder. Biographer J. Randy Taraborrelli said of the singer: "Frank described himself as 'an 18-carat manic depressive'. He was a bipolar, moody, difficult man who drank heavily, with a sense of entitlement twisted by celebrity."

He tried to commit suicide several times. According to Collider, when Sinatra feared being dethroned by Eddie Fisher and the end of his career, he turned on the gas and put his head in his oven. His manager found him before it was too late. Per PBS NewsHour, while in the throes of his volatile marriage to Ava Gardner, Sinatra had at least one other documented suicide attempt with a gun. Gardner tried to wrestle the pistol away from him, the gun went off, but the bullet luckily missed them both. According to Taraborrelli, Sinatra longed for love and companionship but had little understanding of how to maintain a healthy romantic relationship and was always searching for the next best thing.

If you or anyone you know is having suicidal thoughts, please call the National Suicide Prevention Lifeline​ at​ 1-800-273-TALK (8255)​.

Frank Sinatra died of a heart attack at the age of 82 on May 14, 1998, at Los Angeles' Cedars-Sinai Medical Center. His wife, Barbara Marx, and his three children were at his bedside. According to PBS NewsHour, Sinatra's last remaining years were filled with significant health problems, such as heart and breathing problems, high blood pressure, pneumonia, and bladder cancer. He had also been diagnosed with dementia, brought on by Alzheimer's. As the end approached, Sinatra seemed to recognize that his time had arrived, as his last words to his wife were, "I'm losing."

Smithsonian reports that Sinatra was buried with a pack of Camel cigarettes, a bottle of Jack Daniel's whiskey, a Zippo lighter — all of his favorite brands — and a dollar's worth of dimes. In a Rolling Stone interview, singer Bono of U2 spoke on the death of Sinatra — with whom he performed a duet — and the loss of an iconic performer: "Frank Sinatra was the twentieth-century, he was modern, he was complex, he had swing and he had attitude. He was the boss but he was always Frank Sinatra. We won't see his like again."