The Many Loves of Frank Sinatra’s Life

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During his famous and frisky life, Frank Sinatra was married four times — and had affairs with hundreds of more women. So who was the true love of Sinatra’s life?

Nancy Barbato

Frank Sinatra and Nancy Barbato, via The New York Times

Frank Sinatra met Nancy Barbato, a fellow New Jersey native, in the summer of 1934. At that time, Sinatra was already professional singer though he had no serious success. It was not until 1939, the same year he married Barbato, that his music career hit a stride. As the new lead singer of the Tommy Dorsey band, Sinatra began to get noticed, churning out regular radio hits. Dorsey was made the godfather of Sinatra and Barbato’s first child, born in 1940.

The same year, the young family moved to Hollywood — which is where their marital trouble began.

Ol’ Blue Eyes, who was always no trouble landing ladies, began to cheat on Barbato. First, with Marilyn Maxwell, who starred on USO tours alongside Bob Hope. But there were also many others. Although Barbato knew, she had a second child with her husband in 1944, Frank Jr. Soon after, she considered leaving Sinatra and had an abortion when she became pregnant in 1946.

Still, Barbato remained with the unfaithful Sinatra for four more years. THey had a third child together, Tina, before announcing their separation in 1950 — soon after Sinatra’s affair with Ava Gardner became public knowledge.

Though Gardner would quickly become Sinatra’s second wife, Barbato remained in Sinatra’s life. As he maintained with their three children, the ex-couple spoke often over the years, on the phone and at family get-togethers.

Barbato died in 2018 at age 101, outliving both Frank and Frank Jr.

Ava Gardner

Frank Sinatra and Ava Gardner, via Showbiz Cheatsheet

The sultry Ava Gardner made a name for herself acting in noirs like The Killers — which meant that Frank Sinatra had left a nice Italian girl for a literal femme fatale. He was dragged in the press for it, becoming a target of powerful gossip columnists Louella Parsons and Hedda Hopper, and even the Roman Catholic Church.

But the partnership quickly paid off. Garder used her connections to secure Sinatra a part in From Here to Eternity, the drama which solidified Sinatra’s burgeoning film career and earn him his only Oscar. From the outside, Sinatra and Gardner had the makings of a Hollywood power couple — but the relationship was always doomed.

They married in 1951 — days after his divorce from Nancy Barbato was finalized — but both Gardner and Sinatra continued to sleep around. Both were busy, often working on-location, and when together, they fought constantly. The fights were explosive. Gardner drank heavily and she alleges that Sinatra abused pills. Once, she said, Sinatra fired gun into a pillow after one of their fights.

“The trouble was Frank and I were too much alike. [My sister] Bappie said I was Frank in drag. There was a lot of truth in that. He was the only husband I had that Bappie didn’t approve of straight off the bat. I’m not saying she disliked him. On the contrary, she thought he was great—but not for me. I should have listened to her.”

— Ava Gardner, via Vogue

In all, they were married for six years, during which time Gardner had two abortions — a choice which she connected to MGM’s strict penalties for pregnant stars.

Before Sinatra, Gardner had been married twice: first to Mickey Rooney, then bandleader Artie Shaw. After Sinatra, she never remarried. Sinatra, too, remained single for many years… until he met the young Mia Farrow in 1966.

Mia Farrow

Frank Sinatra and Mia Farrow, via The New York Post

“I got a bottle of Scotch that’s older than you” Dean Martin said in his famous toast to Mia Farrow, the night she went public with Frank Sinatra.

Farrow was a virgin, just 19, when she first caught Sinatra’s eye. A rising star on Peyton Place, Farrow bumped shoulders with the older singer while visiting a friend on a movie set. Soon after, he invited Farrow on a fateful trip to Palm Springs in his private jet. Farrow was nervous at first but eventually Farrow succumbed to Sinatra’s charms.

Farrow spent a lot of time with Sinatra at the Palm Springs estate which, according to the podcast You Must Remember This, was still plastered in photos of Ava Gardner. But before long, Farrow became the main woman in his life, embedded into his busy world populated with powerful, older men.

They married in Las Vegas in 1966, when Farrow was 21. But the turbulent decade wore on, Farrow grew apart from her increasingly conservative husband. Farrow began taking edgier parts — that put her at direct odds with the old-fashioned crooner.

She eschewed a chance to co-star in The Detective, a Sinatra-led film, in order to accept her breakthrough role in Rosemary’s Baby, the visionary horror directed by Roman Polanksi. It was the last straw for Sinatra, who served Farrow divorce papers while she was acting on set. Soon enough though, Polanki’s film would crush The Detective at the box office and, during the summer of 1968, Farrow emerged as not only a talent to watch but a true counter-culture icon.

Despite the harsh serving, Farrow and Sinatra remained involved for some time. And in 2013, 15 years after Sinatra’s death, Farrow dropped a bombshell revelation in Vanity Fair: that her son Ronan Farrow is “possibly” Sinatra’s biological son.

Ronan — an award-winning journalist — had always been considered the only biological child shared by Farrow and her estranged husband Woody Allen. So naturally, controversy ensued. And Ronan had a hilarious response, tweeting at the time: “Listen, we’re all *possibly* Frank Sinatra’s son.”

Barbara Marx

Barbara Marx and Frank Sinatra, via Desert Sun

Barbara Marx, also called Barbara Sinatra and born Barbara Ann Blakeley, was Frank Sinatra’s fourth wife. After marrying in 1976, they remained together until Sinatra’s death in 1998 — and it was the longest-lasting marriage for both of them. Marx, a former model, had been married twice before.

First, to Robert Oliver a man with whom she had one son, Bobby Oliver. Following their split, Marx married Zeppo Marx — the last surviving Marx brother — which is how she earned her famous surname. Of course, that name was soon supplanted by superstar Sinatra’s. She married Ol’ Blue Eyes in 1976.

Professing to have found religion in his older age, it appears that Sinatra was faithful to his final wife. He even had his marriage to Nancy Barbato — the only other woman he’d married within the Catholic Church — annulled, in order to make things extra official.

Despite her high-profile marriage, Marx has maintained a fairly private identity until her death in 2017 at age 101.

Other Girlfriends

In addition to — and during — those four marriages, Frank Sinatra bedded many women — and many of them were famous too. Among the celebrities, according to FactsVerse:

Vikki Lamotta, the eventual wife of Raging Bull inspiration Jake LaMotta

Nancy Berg, a Vogue cover girl

Jo Lansing, a B-movie pin-up

Zsa Zsa Gabor, the sparkly socialite

Marlene Dietrich, the bisexual German minx

Lana Turner, at the height of her fame

Joan Crawford, at the start of her career

Judy Garland, who remained a lifelong friend

Donna Reed, his From Here to Eternity co-star

Grace Kelly, before she was a princess

Gloria Vanderbilt, America’s favorite heiress

Angie Dickinson, who remained on-and-off with Frank for decades

Leslie Caron, one of the last surviving stars from Hollywood’s Golden Age

Eva Bartok, a Hungarian-British actress

Joan Blackman, a co-star of Elvis Presley

Jeanne Carmen, a model and trick-shot golfer

Lauren Bacall, before she fell in love with Humphrey Bogart

Venetia Stevenson, an actress and future mother to Erin Everly

Judith Exner, a favorite mistress of John F. Kennedy

Gina Lollobrigida, the ’60s sex symbol

Juliet Prowse, whose legs were legendary

Marilyn Monroe, who needs no introduction

Kipp Hamilton, an actress — and Carol Burnett’s sister-in-law

Keely Smith, a jazz singer

Jill St. John, the beloved Bond girl

Natalie Wood, while married to Mia Farrow

Irene Tsu, a popular Chinese actress

Victoria Principal, the star of Dallas

Hope Lang, another Peyton Place alum

Elizabeth Taylor, who reportedly had Sinatra’s abortion

and finally—

Jackie Kennedy, meaning that Frankie and JFK shared (at least) three lovers!

READ MORE: ‘Dear Prudence’ Was Inspired by Mia Farrow’s Sister

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