He did it his way — and it sure seemed like fun. Whether he was performing for crowds of adoring fans, romancing Hollywood’s most beautiful women or spending wild nights out with his famous pals, Frank Sinatra knew how to seize the day. “I would like to be remembered as a man who had a wonderful time living life,” Frank once said. “I don’t think I could ask for anything more than that.” 

But Frank wasn’t as happy-go-lucky as he seemed. Beneath that fun-loving exterior lurked a complicated — and often tormented — man who described himself as an “18-karat manic depressive” and who attempted suicide more than once. Said Frank: “I have an over acute capacity for sadness as well as elation.”

Frank Sinatra’s 4 Marriages: How He Bounced Back

Indeed, as confident as he seemed, Frank also felt isolated and insecure. An only child in a New Jersey neighborhood where big families were common, he was lonely growing up and longed for a sibling. “I used to wish I had an older brother that could help me when I needed him,” he recalled. “I wished I had a younger sister I could protect.” 

He found the love he craved as a teen idol, but his grasp on his newfound fame was so tenuous that envious over the success of Eddie Fisher, Frank attempted suicide by putting his head in an oven and turning on the gas. And even after his manager rescued him, he remained troubled for years by conflicting emotions. “He wanted to be famous, but when he became famous, he didn’t like it,” says Donald Clarke, author of All or Nothing at All: A Life of Frank Sinatra, adding that while the outgoing crooner enjoyed the trappings of stardom, “he thought … that he should [also] have a private life.” 

Yet it was his private life that caused him the most heartbreak. Married four times, the singer seesawed emotionally while wed to second wife Ava Gardner. “He and Ava had this terribly tempestuous relationship, and it was the most important relationship of his life,” Clarke shares. “He didn’t know what to do.” 

Deeply jealous, Frank drank heavily and argued frequently with Ava during their six-year marriage — and was so terrified of losing her that he attempted suicide three more times. “She treated him cruelly, the way he’d treated every woman before,” says Sinatra biographer J. Randy Taraborrelli. “It humbled him. Frank was devastated.” 

Ultimately, though, Frank bounced back. And after a two-year union with Mia Farrow, the showman found lasting love with his fourth wife, Barbara Marx, whom he married in 1976. That stability, coupled with his close relationships with his three children, brought with it a sense of peace that had eluded Frank in the past. And by the time he passed away in 1998, at the age of 82, Frank was, at long last, content. “Has it been worth it all?” he reflected late in life. “Sure it has, because I love what I’m doing, and I’m one of the happiest people I know.” 

—Alison Gaylin, with reporting by Fortune Benatar
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