Let’s talk about a legend—a guy who lived life on his own terms, and boy, did he live it big. Frank Sinatra wasn’t just a singer; he was a force of nature. Whether he was dazzling crowds, wooing Hollywood’s most dazzling women, or partying into the wee hours with his Rat Pack crew, Frank had a way of making every moment feel like it mattered. “I’d like to be remembered as a man who had a hell of a good time living life,” he once said. And honestly, who could ask for more than that?
But here’s the thing: Frank wasn’t all glitz and glamour. Beneath that smooth exterior was a guy wrestling with some pretty heavy stuff. He called himself an “18-karat manic depressive,” and trust me, that wasn’t just talk. This was a man who felt things deeply—both the highs and the lows. So deeply, in fact, that he tried to end it all more than once. As Frank himself put it, “I’ve got this knack for feeling sadness as intensely as I do joy.”
Frank Sinatra: The Man Behind the Smile
Loneliness in the Spotlight
For all his confidence on stage, Frank was actually a pretty lonely guy growing up. Raised as an only child in a neighborhood full of big families, he felt out of place. While other kids ran around with brothers and sisters, Frank dreamed of having his own family. He wished for an older brother who could look out for him and a younger sister he could protect. It wasn’t until later in life that he found the kind of love and support he’d been craving since childhood.
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And let’s not kid ourselves—fame wasn’t exactly a cure-all for Frank’s insecurities. Sure, he became a teen idol, but that fame came with its own set of challenges. When Eddie Fisher started stealing the spotlight, Frank spiraled into despair. Desperate and feeling unmoored, he attempted suicide by sticking his head in an oven and turning on the gas. Luckily, his manager saved him, but the scars of that moment stayed with him for years. As author Donald Clarke explains in his book All or Nothing at All: A Life of Frank Sinatra, Frank struggled with conflicting feelings about fame. “He wanted it, but once he got it, he didn’t know how to handle it,” Clarke says. Frank loved the perks of being a star, but he also craved privacy—a normal life away from the cameras.
Ava Gardner: The Love That Nearly Broke Him
Frank’s personal life was just as complicated as his professional one. His marriage to Ava Gardner, his second wife, was nothing short of a rollercoaster. They were wildly in love, but their relationship was also fraught with drama. Frank was insanely jealous, and their arguments often turned ugly. He drank heavily and even attempted suicide three more times during their six-year marriage. “Ava treated him cruelly, just like he’d treated other women before her,” says Sinatra biographer J. Randy Taraborrelli. “It broke him in a way nothing else ever had.”
Rebuilding After the Storm
But Frank wasn’t done yet. After a brief, tumultuous marriage to Mia Farrow, he finally found stability with his fourth wife, Barbara Marx. They tied the knot in 1976, and this time, things clicked. With Barbara by his side and his three kids growing up, Frank finally felt the peace he’d been searching for. By the time he passed away in 1998 at the age of 82, Frank was content. Looking back on his life, he said, “Was it all worth it? Absolutely. I loved what I did, and I was one of the happiest people around.”
—Alison Gaylin, with reporting by Fortune Benatar
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