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Swingin’ Facts About Frank Sinatra, The Chairman Of The Board

Eli Artman

Since the early 1940s, the popularity of Frank Sinatra has remained unwavering. This slim, well-dressed Italian kid from Hoboken, New Jersey took the world by storm with his effortlessly smooth, distinct, and powerful voice, and few have matched his level of stardom since. However, behind the legendary voice and charismatic public image, Sinatra lived one of the most interesting lives of the 20th century—full of fun and games, as well as scandal and heartbreak. Just reading about the ups and downs of Sinatra’s experiences makes for a wild experience of its own! Here are facts offering a behind-the-scenes look at the legendary and unique life of Ol’ Blue Eyes himself.


Frank Sinatra Facts

1. The World Almost Missed Out On Frank Sinatra

When Sinatra was born, the doctors tending to his mother were stunned—the baby was born blue and not breathing. They had to use forceps to forcefully yank him out of the womb by the head.

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Assuming that he didn’t make it, they simply laid him on a table and began caring for his mother—and then his grandmother sprung into action. She put young Frank under a cold water tap, causing him to come to.

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This rough entry into the world gave him a scar on the side of his face—a feature which stayed with him for his whole life, at times causing him serious insecurity.

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2. His Mother Had A Secret Life

Frank Sinatra’s parents were both born in Italy and emigrated to the US when they were young.

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When Sinatra was a child, his father fought as a lightweight boxer under the name of Marty O’Brien. His mother worked as a midwife, but behind closed doors, she was keeping a dangerous secret. It’s alleged that Dolly Sinatra ran an underground abortion clinic for local Italian Catholic girls who found themselves in trouble.

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As Sinatra’s own family has said, there was a lot that Dolly was hiding.

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3. His Childhood Scars Drove Him Insane

On top of the scars that Sinatra bore from his complicated birth, he also suffered from a punctured eardrum—and his problems didn’t end there. A childhood surgery left him with even more visible damage, and he suffered from horrific acne in his teens that caused permanent pockmarks and scars.

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This led his schoolmates to call him “Scarface,” leaving the young Sinatra furious—but what better revenge than going on to become a Hollywood heartthrob?

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4. His Family Wasn’t Exactly Picture Perfect

Frank Sinatra’s mother Dolly was incredibly active in the community.

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Between stints as a midwife, she was also a community leader for local Democratic causes and even chained herself to City Hall as part of the women’s suffrage movement. She was incredibly busy, but the rare times she was home, she showed a dark side.

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Dolly continuously butted heads with Frank, even going so far as to belittle him, but that wasn’t the worst part.

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5. His Mother Was Extremely Rough

According to some, Dolly Sinara would hit Frank. While it’s no excuse, but she may have been a product of her environment.

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It’s rumored that the family had mob connections, and Sinatra’s parents ran a bar during the Prohibition era—where else would their stock have come from? It was at the family’s bar where Sinatra would first express his desire to perform.

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He would sing songs while standing on top of the player-piano for change from the barflies.

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6. His Teachers And Family Were Cruel

Sinatra only expanded his musical repertoire from there. After an uncle gave him a ukelele at age 15, Sinatra would use it to perform at family functions.

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He was growing up in the aftermath of the Great Depression, and his desire to become a singer caused both his family and teachers to disapprove. One teacher even said he showed “no real talent for anything,” but Sinatra was determined to prove them wrong.

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7. He Got Thrown Out Of School

As if dealing with a slew of teachers who insulted him wasn’t enough, Sinatra was soon expelled from his high school due to his “general rowdiness”. He only ended up attending high school for 47 days in total.

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When he was expelled, his father was disappointed and furious, but nothing the Sinatras could do would stop Frank from pursuing his musical dreams. His path so far had been rocky—and it was about to get rockier.

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8. His Life Was As Dramatic As Any Movie

Sinatra spent the next few years splitting his time between more traditional jobs and singing gigs around the New Jersey area.

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It was during this era that he got a life-changing gig singing at a roadhouse in Englewood Cliffs, New Jersey. Sinatra thought of it as his big break—but he quickly became entangled in local drama.

His big ego caused his fellow musicians at the restaurant to bristle.

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He also met a beautiful young woman there named Toni Della Penta. It was an exciting time in the young Sinatra’s life, but soon enough, the beautiful fireworks would turn dangerously explosive.

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9. He Was In A Destructive Love Triangle

The drama in Sinatra’s life at this time could’ve been ripped from the script of a teen drama like Dirty Dancing. The young singer became involved with Toni Della Penta, but behind the scenes, he had a dirty little secret. Sinatra had been cheating on her with another girl, Nancy Barbato.

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The two girls feuded, and Della Penta ended up suffering a miscarriage. Sinatra’s reaction was shocking.

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10. It Got Him In Trouble With The Law

After Della Penta attacked Barbato, Sinatra told her that it was over and that he only wanted to be with Barbato, saying that she was pregnant (she wasn’t).

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Della Penta was furious, and she planned a chilling act of vengeance. She went to law enforcement, who then detained Sinatra on charges of “seduction”. (It was a very different time). Della Penta herself was even detained for another fight with Barbato, but Sinatra had made up his mind.

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He married Barbato later that year—but it wasn’t exactly a fairytale romance.

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11. He Wasn’t Always So Suave

The picture many of us have of Sinatra as a classy, well-dressed, sophisticated gentleman is pretty different from his original public image as a skinny, slightly awkward teenage heartthrob in his early days as a radio and movie star in the 1940s. It was only in the early 1950s, when Sinatra signed a record deal with Capitol and was paired with legendary music arranger Nelson Riddle, that he would build himself this new image that we all know today.

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12. He Was A Hit—But He Was Stuck

Frank Sinatra once said:

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“The only two people I’ve ever been afraid of are my mother and Tommy Dorsey”. Dorsey was a famous bandleader who recruited Sinatra to sing for him in 1939. Sinatra was an instant success, but behind the scenes, it wasn’t all acclaim and applause.

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He feuded with drummer Buddy Rich, but even worse, he was stuck in an ironhanded and unfair contract with Dorsey, which signed away a large portion of his lifetime earnings in entertainment.

Sinatra knew he’d have to do something drastic.

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13. He Was A Total Sensation

The reception that Sinatra received in these early days from young female audiences was comparable to what performers like Elvis Presley and the Beatles would receive years later. Although the musical style with which he first rose to fame was very different from the songs we all now know and love, it was thanks to his Big Band background and early fans that his name was put on the map in the music industry.

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But once it was on that map, he wanted to strike out on his own—so he came up with a plan.

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14. His Mentor Ended Up Hating Him

Based on the screams of fans alone, Sinatra knew that he was famous enough to strike out on his own—and be a huge success. So, he sued to break his unfair contract with Dorsey.

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Sinatra eventually won, and the bandleader’s reaction was utterly cold-blooded. Dorsey reportedly told Sinatra: “I hope you fall on your [expletive]”. Dorsey would continue to insult Sinatra to the press until he passed on in 1956—but he may have had another good reason to.

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15. He Might Have Had Friends In Low Places

It was around this time that dark rumors about a possible involvement with the mob began to plague Frank Sinatra.

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People began to whisper that Sinatra had gotten out of his contract in a more chilling way than was reported—that he’d gotten one of his mob buddies to threaten Dorsey until the bandleader agreed to let him go for a few thousand bucks. Whether or not that was true, these types of stories about underworld ties would continue to plague Sinatra…

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16. He Had A Little Help

Despite spending the 1940s as a superstar teenage heartthrob and the object of mass admiration, Sinatra’s publicist George Evans still decided that the young star could use a helping hand. So, he held auditions to see which girls could scream the loudest, and then paid them to strategically sit in spots that would maximize the noise coming from the audience, all to help create the hype around the young star as he launched his solo career.

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17. His Fans Were Rabid

Sinatra might not have needed the help. His fans were devoted to him—to an almost terrifying degree. They’d try to get into his hotel rooms even after he’d left them just so they could touch the bed where he’d slept, or rip the clothing right off his back.

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In one disturbing incident, nearly 35,000 fans started a riot when they couldn’t enter an already-full venue where he was performing.

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18. People Wondered Why He Didn’t Serve

Despite playing a sailor in several movies, one of the early scandals to plague Frank Sinatra’s career was the rumor that he was a draft dodger during WWII. Some spread claims that he had bribed a doctor $40,000 to declare him medically unfit to serve.

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The FBI investigated these claims but found no basis for them.

The real reason that he was rejected by the draft board was the combination of his damaged eardrum, which doctors had punctured at birth, as well as the psychological trouble that he suffered from.

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19. He Had Shady Connections

One rumor that never left Sinatra his entire life was the claim that he was closely connected to the mafia. There may be good reason for this—he not only posed with prominent members of the Chicago mafia in photographs, but even sang at the family wedding of Willie Moretti, a known member of the Genovese mob family, in 1948. Maybe that’s why he called Chicago “My Kind of Town”!

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20. Was His Career Built On Criminality?

It was rumored that all of these mob ties were more than just friendships for Sinatra—some credit his relationship with these notorious figures for helping his career take off. In other words, it was in part by collaborating with the mafia that Sinatra was thrust into the public eye.

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How much he benefitted from his ties is unclear—but later down the line, they’d come back to haunt him.

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21. He Had Strong-Armed…Fans

Comedian Jackie Mason reported that after making fun of Ol’ Blue Eyes in one of his acts, he was threatened and roughed up by gangsters in his hotel room.

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Did Sinatra orchestrate this, or were these guys just super-committed fans? You be the judge…

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22. He Gave Lavish Gifts

Adding to the suspicions that Sinatra had close ties to the mafia, famous gangster Sam Giancana was known to have worn a sapphire friendship ring at all times—reportedly given to him as a gift by none other than Frank himself.

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23. He Had A Roving Eye

The 1940s had a lot of highs and lows for Frank Sinatra and his wife Nancy—and the lows could be gut-wrenchingly bad. They had three children and moved from New Jersey to Hollywood, but it was after this move that Sinatra began to regularly cheat on Nancy with different women.

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In 1945, he began to have an affair with starlet and old friend Marilyn Maxwell. It went on for months, until Nancy discovered in an absolutely devastating way.

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24. His Wife Made A Horrible Discovery

One day, Nancy spotted a beautiful diamond bracelet in Sinatra’s car.

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She assumed it was a gift and played like she hadn’t seen it. Weeks passed, and the bracelet never made another appearance—until she saw it on Maxwell’s wrist at their annual Christmas party. Nancy ordered Maxwell and her husband to leave immediately and unleashed her fury on Sinatra, threatening to leave him.

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Sinatra admitted that he’d been with Maxwell, but said that it wasn’t serious. She forgave him, but their troubles were far from over.

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25. The Tabloids Got A Hold Of The Story

Whispers about the incident at the Christmas party circulated and Sinatra began to regularly appear in the tabloids alongside stories—some true, others just rumors—about his rampant infidelity. His romance with Maxwell was exposed, and it was said that he had a passionate affair with Lana Turner, which she denied.

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Embarrassed and furious, Nancy opted to terminate a pregnancy in 1946 when the couple was on the rocks.

Later, in better times, she gave birth to daughter Tina—but even that couldn’t save the marriage.

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26. He Couldn’t Say No To A Starlet

Sinatra simply couldn’t stop cheating on Nancy, and in 1949, the tabloids caught him and Judy Garland on a romantic vacation.

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Garland and Sinatra had been friends, and she was recovering from a nervous breakdown and hospital stay. At this point, she was also still married. While this wasn’t the last straw for Nancy, her patience was spent—but Sinatra had more to worry about than just his frustrated wife.

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27. He Was A Picky Eater

Sinatra was a man known for his very particular tastes, and food was no exception.

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The fact that he chose Patsy’s, a traditional family-run Italian restaurant in Manhattan, as his favorite place to eat has helped keep the place on the map as a hub for celebrity diners like Tom Hanks, Madonna, and Stephen King, even more than 70 years later.

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28. He Suffered From Horrible Depression

Sinatra’s suave facade hid a lifetime of secret pain.

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The singer suffered from severe depression, and while he could often hide it well, he would suffer from erratic and brutal mood swings that would cause him to lash out at those around, occasionally with force.

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He couldn’t handle criticism or negative attention, and would react violently to journalists, photographers, and publicists.

Of course, these outbursts would only attract more scrutiny, creating a cycle that would later culminate in a horrific incident.

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29. It Was Love At First Sight

The story goes that Sinatra promised himself he would marry movie star Ava Gardner the very first moment he saw a photo of her in a magazine. He was smitten from the first time they met, but she was initially unimpressed.

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Finally, she warmed to him, and they began a passionate affair—but this wasn’t like his other dalliances. He was utterly obsessed with her. He knew he had to be with her—but at what cost?

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30. It Was The Nail In The Coffin

In 1950, Sinatra had been married to Nancy for nearly a decade.

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They’d had three children together and weathered his rise to fame—not to mention his serial philandering. But when Sinatra told Nancy that he’d been having an affair with Ava Gardner, it was the last straw.

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She locked him out of the house and contacted a lawyer. The date that the couple announced their separation? Valentine’s Day 1950. That must have been fun.

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31. When He Was 35, It Was A Very Bad Year

With his divorce from Nancy pending, Sinatra was finally free to be with Ava Gardner.

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It should’ve been one of the happiest times of his life—but it quickly turned horrifically sour. Sinatra’s presence in the tabloids had ruined his reputation, and his career suffered horribly as a result.

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32. He Lost His Best Friend

No one had been as instrumental to Sinatra’s career as his publicist George Evans, and in early 1950, Sinatra suffered a staggering loss when Evans suddenly passed following a heart attack. He was absolutely devastated, and things were only about to get worse.

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Whenever Sinatra was distraught, he would suffer physical symptoms. He’d lose his voice or suffer from horribly painful throat hemorrhages, which would force him to cancel performances, further fueling the stress and frustration.

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33. His Second Marriage Was A Nightmare

One Sinatra’s divorce from Nancy was finalized, he wed Ava Gardner in a small ceremony in 1951.

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He was finally with the woman of his dreams, but their marriage was no fairytale. Both loved their vices, from drinks to gambling, and they frequently got into brutal fights and altercations that would land them, once again, on the pages of the tabloids.

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Less than two years after they were married, they announced their separation—but their story didn’t end there.

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34. He Was Losing It

Thanks to his highly-publicized affair with and subsequent rocky marriage to Gardner, Sinatra’s career was floundering.

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Where he’d once sold out huge rooms three times over, he could barely fill a 1,200-seat theater. He had to ask two different record labels to borrow $200,000 to pay back taxes—one rejected him and one lent him the money, but both later dropped him. It was a truly dark time in Sinatra’s life.

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35. It Was His Darkest Hour

In the early 1950s, when his career was a devastating low point, Frank Sinatra once stumbled upon a crowd of young girls, akin to the kind he had regularly attracted early in his career, lining up to see young singing star Eddie Fisher.

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In what was probably his darkest moment, Sinatra saw this scene and immediately felt that the world no longer wanted him, leading him to attempt suicide by sticking his head in his oven. Thankfully, his manager walked in just in time to save his life.

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36. He Was Stuck In The Middle

Following in the footsteps of his mother, who was once a ward leader for the Democratic Party, Sinatra was very politically active for most of his life as a celebrity advocate and worked to drum up votes for Democratic candidates.

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He had a long friendship with John F. Kennedy and often campaigned for him—but the relationship also put him in a great deal of jeopardy. 

Sinatra’s mob connections were unimpressed with his proximity to the Kennedys, who were using their power to crack down on the mob. Regardless, Sinatra stayed close to Kennedy—until the President dealt him a heartbreaking betrayal.

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37. He Was Caught In A Witchhunt

At one point during his liberal activist days Sinatra’s detractors accused him of being a Communist sympathizer—allegations which Sinatra denied and dismissed, stating that “I don’t like Communists, and I have nothing against any organization except the Knights of Columbus”. Good to know.

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38. He Was Wildly Jealous

A madly jealous Sinatra partially blamed the problems in his relationship with Ava Gardner on her inability to get over her former boyfriend and his fellow Rat Packer, Peter Lawford—and he went to disturbing lengths to keep them apart. Sinatra once called Lawford in the middle of the night and said he’d send men to break Lawford’s legs if he was ever seen with Gardner again.

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Unfortunately, threats aren’t really a great way to save a marriage.

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39. His Close Friend Pushed Him Away

Frank Sinatra was John F. Kennedy’s biggest and most outspoken celebrity supporter, and was even the headline performer at Kennedy’s inaugural ball. However, this relationship abruptly fell apart after Kennedy snubbed Sinatra on a 1962 visit to California, when the president elected to stay with singer Bing Crosby instead of staying at Sinatra’s home as planned.

Sinatra was reportedly so offended by the snub that he personally smashed the concrete heliport that had been built for the occasion with a sledgehammer.

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40. He Stood Up Against Intolerance

Fighting intolerance and discrimination was one of the issues that Sinatra was always extremely passionate about. On one occasion, he insisted that his friend and fellow singer Nat King Cole join him in the dining room of a segregated hotel, willing to fight or remove all his business from the hotel if anyone tried to stop them.

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Through a series of incidents like this, Sinatra played a role in fighting Jim Crow laws in the United States.

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41. He Made A Good Ex

Sinatra’s serial philandering destroyed not only his first marriage, but also his second, to Ava Gardner.

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However, Sinatra remained close with both Nancy and Gardner for the rest of their lives. When he was at the lowest point of his career, it was Gardner who pushed for him to be cast in the film From Here to Eternity. It would wind up sparking a huge comeback—but behind the scenes, Sinatra’s life was more tumultuous than ever.

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42. He Had A Famous Rival

Hollywood superstar Humphrey Bogart once refused to attend his own wife’s birthday party due to his fear that the crooner would seduce her. Though Sinatra and Bogart’s wife Lauren Bacall did in fact become quite close, probably stoking Bogey’s fears, their relationship didn’t become romantic until after Bogart’s passing in 1957, and there were even rumors that they were briefly engaged.

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43. He Moved Through The World In Mysterious Ways

Sinatra’s work in From Here to Eternity got him an Oscar nomination for Best Supporting Actor, sparking a comeback for the embattled star. There are differing stories as to how he got the part—while some of his biographers have said that it was Gardner who pushed for it, other rumors said that he’d used his mob connections to pressure the producers to give him the part. This story would get even more twisted from there…

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44. His Story Inspired An Unforgettable Movie Scene

The character of Johnny Fontane in The Godfather is believed to have been based on Frank Sinatra. Sinatra, for one, did not appreciate being depicted as tied to the mafia, fearing that this would hurt his public image.

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The rumors about Sinatra using his mob connections to get his part in From Here to Eternity likely inspired the infamous horse’s head scene in The Godfather. 

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45. His Friends Were Notorious

Despite coming to be known as the Rat Pack by the public, Sinatra and his friends actually preferred to call themselves the “Summit” or the “Clan”.

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I guess, when you think about it, “Rat Pack” isn’t exactly a flattering name. It was originally rumored to have come from Lauren Bacall, who, upon seeing her husband Humphrey Bogart, Sinatra, and their friends in the wee hours of the morning, said “You look like a goddamn rat pack”.

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46. He Was With One Of The Most Famous Stars Ever

Following his comeback in the mid-50s, no one could touch Sinatra’s success for the next decade. His albums were hits, his films were critically acclaimed, and he was constantly surrounded by not only the Rat Pack, but a large group of A-list stars.

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Life was good. It was around this time he met his friend Joe DiMaggio’s new wife—a blonde bombshell by the same of Marilyn Monroe.

The word “bombshell” would prove to be very apropos, as the relationship between the three was utterly explosive—but more on that later.

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47. None Of His Relationships Lasted

During this time, Sinatra was also involved with a number of other women, including model Angie Dickinson and actress Juliet Prowse.

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They were even engaged, until Sinatra broke it off for an utterly cruel reason. He wanted her to put her career on hold for their marriage, but she refused. This controlling behavior would be a chilling red flag for what was to come.

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48. His Son Was Kidnapped

Sinatra remained a devoted father even after his divorce from Nancy, but in 1963, he lived through every parent’s worst nightmare. On the evening of December 8, 1963, Frank Sinatra Jr. was kidnapped from his hotel room in Tahoe.

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Soon after, a call came through with the kidnapper’s demands: they wanted Sinatra’s money. A lot of it.

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49. He Was Never The Same

The kidnappers asked for $240,000—about $2 million in today’s money—and told him to only call them through payphones. Sinatra began carrying rolls of dimes in case he needed to call them, a habit that would stay with him for the rest of his life.

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He gathered the money and prepared for the exchange. Thankfully, after two days in captivity, Frank Jr. was released—but the stress and trauma stayed with Sinatra for the rest of his life.

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50. It Was All Happening At Once

Sinatra was making a film with the Rat Pack at the time that his son went missing.

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And on top of that, he was mourning the loss of an old friend—President John F. Kennedy had been shot just weeks before the kidnapping. They’d never had the chance to reconcile after their falling out.

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It got so bad that Sinatra considered ceasing production completely, but eventually, he was able to return to set. However, the kidnapping still hung heavy over his mind.

Frank Sinatra facts
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51. Something Wasn’t Right

There were bizarre elements to the kidnapping that haunted Frank Sinatra.

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He’d been so frantic and concerned when he received their initial call, that when they demanded $240,000, he told them he’d give them $1 million. Strangely, the refused. The team behind the kidnapping was later apprehended by law enforcement and found guilty after a trial, but the ringleader appealed and claimed that he was legally insane during the kidnapping.

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None of them ended up serving very long sentences.

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52. He Was A High Roller

During the Rat Pack years, Sinatra branched out into casino ownership, purchasing the Cal Neva Lodge & Casino, which straddled the border between Nevada and California.

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It quickly became a celebrity hotspot, hosting guests like Marilyn Monroe, Lena Horne, and Lucille Ball. He was living the high life—but one small misstep would ruin it all. When authorities spotted Sinatra’s old pal—and notorious gangster—Sam Giancana on the premises, they took the casino’s license away.

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53. He Was Boxed In

Sinatra was stuck between a rock and a hard place.

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He was facing pressure from his friends in the mob, but the Nevada Gaming Commission and the FBI were cracking down on mob involvement in casinos on the other side. Eventually, he was forced to make the heartbreaking decision to pull out of the Cal Neva.

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It also effectively ended his relationship with Giancana, after years of friendship. Sadly, Sinatra seemed to have a knack for losing friends.

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54. He Self-Sabotaged

When Sinatra was 50, his newest romantic relationship shocked the tabloids: he’d fallen for actress Mia Farrow, who was just 21 years old at the time.

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The couple didn’t know it, but they were doomed to a brutal end. Once again, Sinatra was very controlling of his young bride, demanding she give up her career. Surprisingly, Farrow agreed, shocking the nation by leaving the soap opera Peyton Place at the height of her rising star.

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55. He Was About To Lose Her

At this point in her career, Farrow became known more for her high-profile marriage to Sinatra than her mettle as a serious actress.

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However, an incredible opportunity was about to come knocking. Farrow was offered the prestigious leading role in the classic horror film Rosemary’s Baby—but little did she know, it would come at a great cost.

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56. He Dealt A Heartbreaking Blow

After marrying Sinatra and putting her career on hold in 1966, Farrow spent two long years playing housewife while he continued to work.

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Bored of her bland, domestic lifestyle, she agreed to play the role of Rosemary Woodhouse in Roman Polanski’s Rosemary’s Baby. As the movie’s shooting schedule ran over time, Sinatra grew furious—and lashed out in a devastating way. Sinatra served Farrow with divorce papers with no warning, while she was still on set.

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57. She Lost It All

Farrow had already considered dropping out of the film because of the strain it placed on her marriage, but allegedly, a studio exec told her that she’d win an Oscar if she did it. She was still completely devoted to Sinatra, but she couldn’t say no o the opportunity.

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Famously, Farrow was nominated for multiple awards for Rosemary’s Baby, but no Academy Award—a move now seen as one of the most legendary snubs in Oscar history.

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58. He Couldn’t See Both Sides

Although Sinatra had urged Farrow to quit acting when they wed, he actually planned to cast her in one movie:

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his passion project The Detective. And so, when filming for Rosemary’s Baby took longer than anticipated, Sinatra was extremely furious. He recast Jacqueline Bisset in his wife’s role, and cruelly divorced Farrow.

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59. They Loved Each Other For The Rest Of Their Lives

Despite Sinatra’s callous behavior during the dissolution of their marriage, Farrow later admitted that when she was with Sinatra, she acted like an immature teenager, which contributed to the strain on their relationship. After their divorce, they managed to put the past in the past, with the pair even staying close friends until the legendary crooner’s passing.

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60. He Might Have Had Secret Children

He was incredibly rich, incredibly famous, and known for his philandering–it seemed inevitable that a few people would crawl out of the woodwork and try to get a piece of the pie. Actress Eva Bartok claimed that her daughter was the product of a passionate affair with Sinatra from the 50s.

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Another woman who had been born in 1943 to a showgirl claimed she was Sinatra’s progeny, even changing her family to Sinatra in the year 2000.

Surprisingly, she was actually given $100,000 from his estate after his passing, although her claim was never substantiated.

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61. He Was Generous With His Time And Money

Sinatra could be incredibly rough with both strangers and loved ones, but he also had a surprising soft side. When his friend Lee J. Cobb suffered a heart attack in 1955, Sinatra swooped in and sent books, flowers, and food to his bedside–and that’s not all.

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He also paid Cobb’s medical bills and visited him in hospital every day, offering words of encouragement to keep his friend’s morale up. It wasn’t his only act of kindness.

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62. He Was Always There

Sinatra stayed friends with Ava Gardner even after their divorce, and took care of her finances throughout the 60s, when starlets were getting swindled out of their fortunes left and right (see:

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Debbie Reynolds). When Gardner fell ill in the 80s, he put $50,000 toward her medical bills and urged her to come to the US for special treatments. Sadly, she was too frail, and she passed on in 1990.

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63. He Got Married One Last Time

After years of tumultuous marriages and passionate affairs, Sinatra finally met a woman that he could stay with for the rest of his life. Sinatra’s fourth and final wife, Barbara, was no stranger to Hollywood marriages—her second husband was Herbert “Zeppo” Marx, of the legendary Marx Brothers comedy team. While they’d stay married for 22 years, until Sinatra’s passing, they still had their fair share of drama…

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64. He Was A Neat Freak

According to his final wife Barbara, Sinatra was obsessed with cleanliness and often showered up to 12 times a day.

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When did he find the time to do anything else?

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65. The Tragedies Kept Piling On

Sinatra spent time performing at Caesar’s Palace in 1977. His mother was planning on coming to see one of his shows–but sadly, she never made it. Dolly Sinatra was traveling in a small plane with three others when it crashed on the way to Las Vegas.

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There were no survivors. Sinatra was utterly devastated–and he never truly recovered from that day.

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66. It Changed His Outlook

Their relationship had been fraught at times, and Sinatra had a truly hard time coping with the passing of his mother.

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This tragedy is credited with having led him to return to the Catholic faith in which he was raised. Prior to that point, Sinatra had long been an outspoken critic and skeptic of organized religion, while still maintaining a personal belief in a higher power and spirituality.

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67. He Didn’t Suffer Alone, Sadly

The tragedy of Dolly’s loss ended up becoming one half of a sad and eerie coincidence. Both Sinatra’s mother and fellow Rat Pack superstar Dean Martin’s son lost their lives in plane crashes on the exact same California mountain, ten years apart from one another. Spooky.

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68. He Couldn’t Go On

Sinatra tried to soldier on after learning of the devastating loss. After all, the show must go on. But after performing two of the shows he was scheduled to do, he couldn’t take it anymore.

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He walked away and canceled the rest of his shows at Caesar’s Palace. He later retreated to Barbados to recover from the loss, before eventually rallying two months after the crash to perform for Princess Margaret in London.

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69. His Hit Angered Its Songwriter

One of Sinatra’s most iconic songs was his 1977 rendition of “New York, New York”. And as much as the public loved it, one person who felt otherwise was the song’s author, who was not pleased with Sinatra’s creative additions of his own words and phrases to the original lyrics. This was not the first time Sinatra had messed around with song lyrics to the chagrin of the original composer, doing so most notably with Cole Porter a few decades earlier.

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70. He Had An Unwanted Fan

Lee Harvey Oswald, the man who shot JFK, had reportedly watched Sinatra’s film Suddenly just a few days the infamous incident. When Sinatra heard about this, he asked United Artists to remove the film from circulation entirely.

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71. He Could Give It Out And Take It

When Sinatra was the subject of one of the classic “Dean Martin Roasts” in 1978, one of the most memorable roasters to take a stab at Ol’ Blue Eyes was his old Hollywood buddy, future president Ronald Reagan.

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Roasted by the President? Not bad!

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72. He Had A Dramatic Change Of Heart

Speaking of, despite decades of very public and passionate activism on behalf of liberal causes and Democratic candidates, Sinatra’s political outlook made a near-complete 180 starting in the early 1970s. Following what he viewed as a shift in the policies of the Democratic party, as well as the rise of his old friend Ronald Reagan to prominence in the Republican party, (plus, you know, getting older) Sinatra became an outspoken conservative, even becoming Reagan’s official “fundraising ambassador”.

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73. Everyone Wanted His Story

Sinatra lived one of the most fascinating lives of the 20th century, so it’s not surprising that biographers were chomping at the bit to get his story down on paper as he entered his golden years.

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And that’s not even to mention the “unofficial” biographers. One in particular was feared by Old Hollywood stars–Kitty Kelley, who had already written unofficial biographies about Jacqueline Kennedy Onassis and Elizabeth Taylor.

When it was announced that Sinatra was her next target, he was furious and determined to make her pay.

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74. He Couldn’t Stop Her

Sinatra filed a lawsuit worth $2 million in order to prevent Kelley from writing her unofficial biography of him, which was going to talk about his marriages, affairs, and connections to the mob. Who knows the reason why–maybe it’s because what appeared in her book was too close to the truth–but either way, he dropped the suit, and Kelley’s book My Way was released to critical acclaim and quickly became a bestseller. His secrets were out.

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75. He Was Aging…But In Denial

The ordeal took a toll on Sinatra’s health, and his daughter blamed Kelley for many of his problems in the 80s. Still, he didn’t want to stop performing, and he reunited the Rat Pack in 1987.

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It should’ve been great–old friends reunited, singing for adoring crowds of fans–but it quickly devolved into a total nightmare. 

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76. The Tour Was A Disaster

The interpersonal dynamics on the tour were totally twisted. First, Sinatra refused to speak to Sammy Davis Jr.

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, because of Davis Jr’.s use of illicit substances. Davis Jr. was also having financial problems, and claimed that Sinatra’s team had promised him millions of dollars just to do the tour–but instead, he claimed that he watched as Sinatra’s guys lined their pockets with his cash every night. Sadly, the ordeal wasn’t over yet.

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77. He Was Losing Friends Left And Right

Everything changed when Sammy Davis Jr. was diagnosed with throat cancer in 1989. As one of the legs of the tour finished up, Sinatra presented Davis with a gold watch to thank him for being there.

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Soon after, Davis Jr. passed away–and was buried with the gold watch that his old friend Sinatra had given them. It was a sad ending to their friendship–but not as sad as what happened with Dean Martin.

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78. Martin Was A Hot Mess

The tour had been announced nine months after Dean Martin’s son had been the victim of a plane crash on the same mountain where Sinatra’s mother had lost her life–and Martin wasn’t handling it well.

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He was drinking a lot and depending on other substances to get through his grief. Sinatra told Davis Jr. that one of the reasons he wanted to do the tour was to get Martin out of the house.

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It didn’t exactly go as planned.

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79. The Rift Was Deep

Within the first few shows, it was clear that neither Martin’s head nor heart was in it. He even threw a lit smoke into the audience at one of the performances.

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After just five shows, the writing was on the wall, and Martin left the tour. His failure to get it together caused a huge rift in his friendship with Sinatra, and sadly, the pair never spoke again.

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80. The Writing Was On The Wall

After returning from the disastrous tour, Sinatra’s health worsened. Still, he managed to make two of the biggest albums of his career, Duets and Duets II, performing, you guessed it, duets of his classic songs with contemporary artists. His frail state was most apparent in concert, where he would often become confused or forget the lyrics to his songs.

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It was heartbreaking to watch, but the worst was yet to come.

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81. He Tried To Fight Til The Very End

Sinatra’s finals years were nothing short of a battle for his life. He suffered from heart problems, breathing issues, pneumonia, dementia, and bladder cancer.

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The entire time, his wife Barbara was by his side. When he suffered a heart attack in May 1998, she begged him to keep fighting–that’s when he uttered his heartbreaking final words: “I’m losing”.

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Sinatra passed away that day at the age of 82–but his story didn’t end there.

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82. His Family Was Torn Apart

Soon after Sinatra’s passing, his daughter Tina made a truly disturbing claim: she said that her stepmother Barbara hadn’t contacted her or her siblings Nancy and Frank Jr.

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when Sinatra was on his deathbed, and they hadn’t had the chance to say goodbye to their beloved father. Tina Sinatra claimed that this had been a deliberate choice by Barbara, who knew that they were close to the hospital.

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83. His Funeral Was Touching

Sinatra’s funeral was a star-studded gathering, with family and scores of A-list friends attending to pay their respects. Sinatra’s family put together a heartbreaking series of his favorite things to bury him with, including cherry-flavored Life Savers, Tootsie Rolls, a bottle of Jack Daniel’s, a pack of Camel cigarettes, a Zippo lighter, a dog biscuit–and perhaps most poignantly, a roll of dimes.

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After his son’s kidnapping, he had never been without one.

However, while Sinatra passed more than two decades ago, dark revelations about the star continue to emerge to this day.

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84. It Was A Match Made In Misery

For all his matches, Sinatra’s second marriage to movie star Ava Gardner was the most explosive: short-lived, widely publicized, and extremely turbulent.

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The couple spent much of their two years together on the pages of tabloid magazines and newspapers, and not exactly for being the fairytale couple he’d hoped they’d be.

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85. He Thought He’d Never Smile Again

Sinatra was so devastated by his split with Ava Gardner that he was reportedly found in the elevator of his apartment building with his wrists slashed just a few weeks after the separation.

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It wouldn’t be his only desperate and dramatic act after a bad breakup that he’d be party to.

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86. He Was Always Geting Into Trouble

Sinatra and baseball star Joe Dimaggio were friends–but they were also both obsessed with starlet Marilyn Monroe.

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DiMaggio and Monroe had been married, but were separated. One night, the two were carousing when they began to suspect that Monroe was with another man. They enlisted the help of a friend and came up with a truly disastrous plan.

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87. They Made A Truly Dumb Mistake

The amateur gumshoes approached the house of Hal Schafer, Monroe’s lover–or so they thought. They burst in the door, hoping to catch Monroe in the act–but all they caught was the ire of an extremely frightening secretary named Florence Kotz.

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They were at the wrong house! For this harebrained scheme, Sinatra and DiMaggio were ordered to pay her $75,000.

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88. He Dumped Marilyn Monroe

Friendship with DiMaggio or not, Sinatra eventually began a relationship with Marilyn Monroe in 1961. They even talked about getting married, but Sinatra broke it off around the time he got engaged to Juliet Prowse.

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However, Monroe got a parting gift: Sinatra gave her a Maltese terrier which she named Maf, short for Mafia Honey. Subtle.

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89. He Was Always Being Watched

Following Sinatra’s passing, it was revealed that the FBI had kept him under surveillance for five whole decades. The reasons were multiple, from his ties to the mob to his close relationship with the Kennedy family.

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Of course, there were all relevant in the 60s…did they just forget to turn the bugs on the phones off after that? Over the years, the Bureau amassed an impressive file of no less than 2,403 pages on Sinatra.

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Strangely enough, even more dark revelations have surfaced since. 

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90. He’s Still Caught Up In Scandal To This Day

As Mia Farrow’s son Ronan grew up, rumors began to spread that he was actually Frank Sinatra’s son. Although his mother, Mia Farrow, was with comedian Woody Allen at the time of his birth, those who have speculated that Sinatra was “possibly” his true father have recently included Woody Allen, Mia Farrow, and even Ronan himself! This might be a welcome revelation for Ronan, who no longer speaks to his other “father,” Woody Allen, due to the many discretions he’s been accused of.

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Sinatra’s daughter Nancy denied the accusations, but you’ve gotta admit, the man looks a little bit more like Ol’ Blue Eyes than Allen.

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Sources1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30

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