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“People often remark that I’m pretty lucky. Luck is only important in so far as getting the chance to sell yourself at the right moment. After that, you’ve got to have talent and know how to use it.” —Frank Sinatra

Who can forget these epic words and the epic voice that made them famous? 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 42 facts offering a behind-the-scenes look at the legendary and unique life of Ol’ Blue Eyes himself.


42. For Once in My Life, Believe Me

Despite playing a sailor in several movies, one of the early scandals to plague Sinatra’s career was the rumor that he was a draft dodger during WWII. Even after claims that he had bribed a doctor $40,000 to declare him medically unfit to serve, the FBI accepted his reasoning that his punctured eardrum and psychological trouble genuinely had him declared unfit fit for service, and that’s why he never joined the army.

41. Strangers in the Night

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 crime family, in 1948. Maybe that’s why he called Chicago “My Kind of Town”!

40. Getting the World on a String

It seems that all of these mob ties were more than just personal 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. Should we be disturbed by this, or grateful that they gave us the opportunity to experience his talent?

39. Allegations

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

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38. Someone to Watch Over Him

Sinatra racked up quite a large FBI file over the course of his lifetime. Beginning with his arrest in 1938 for “adultery and seduction” (some very Sinatra-esque charges), his lasting habits of fighting, drinking, and womanizing, as well as his advanced ties to the mob, kept him on the Feds’ radar for decades—amassing an impressive file of no less than 2,403 pages.

37. It Was a Very Good Year

“Sinatramania” broke out in the early 1940s with its namesake as the lead singer of the “Pied Pipers,” a vocal group which accompanied the Tommy Dorsey Orchestra. The reception he received in these early days from young female “Bobby soxer” audiences (named because of the bobby style socks they wore) was comparable to what performers like Elvis Presley and the Beatles would receive years later. Although this musical style and genre in 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 Bobby soxer fans that his name was put on the map in the music industry.

36. Luck Be the Ladies

Despite spending the 1940s as a superstar teenage heartthrob and the object of mass Bobby soxer 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.

35. Doing It His Way

Sinatra was expelled from high school due to mischievous behavior and never ended up graduating. Despite this, he has both a prestigious arts school in New York and a student center at Hebrew University in Jerusalem named after him.

34. You Make Me Feel So Young

Frank Sinatra’s parents were both born in Italy and emigrated to the US when they were young. His father was born Saverio Antonino Martino Sinatra and went by Anthony Martin “Marty” Sinatra in his later life, while his mother was born Natalina Maria Vittoria Garaventa and eventually went by Dolly Sinatra. During his childhood, Sinatra’s mother worked as a midwife, and also likely operated an illegal abortion clinic, while his father fought as a lightweight boxer under the name of Marty O’Brien.

33. Man of Many Talents

In addition to his illustrious singing career, Sinatra starred in several successful dramatic roles, including the 1962 Academy Award-nominated thriller The Manchurian Candidate.

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32. Love & Marriage

Frank Sinatra’s first marriage to Nancy Barbato ended when it was revealed that he was having an affair with movie star Ava Gardner. The date that the couple decided to end their eleven-year marriage? Valentine’s Day. That must have been fun.

31. Anything Goes

Rumors have often surfaced that Ronan Farrow is actually the son of Frank Sinatra. 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. You’ve gotta admit, the man looks a little bit more like Ol’ Blue Eyes than Allen.

30. Innovations

Sinatra is credited with having developed the first concept album and box set with the release of The Voice of Frank Sinatra in 1946. These essential format innovations have been standard in the music industry ever since.

29. Tragedy

Sinatra had a hard time coping with the death of his mother in a 1977 plane crash, and 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.

28. Fly Me to the Moon—Gone Wrong

Both Sinatra’s mother and fellow Rat Pack superstar Dean Martin’s son died in plane crashes on the exact same California mountain, ten years apart from one another.

27. The Way You Look Tonight

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, current marital and family considerations be damned. His dream ultimately would come true, as the couple married in November 1951.

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26. Rivals

Hollywood superstar Humphrey Bogart once refused to attend a party with Sinatra due to his fear that the crooner would seduce his his wife and co-star Lauren Bacall. Though the Sinatra and Bacall did in fact become quite close, probably stoking Bogey’s fears, they were never in an actual relationship (publicly, at least, there were of course rumors).

25. Dissent

As much as the public loved Frank’s rendition of “New York, New York,” 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.

24. Ring Leader

Adding to the suspicions that Sinatra had close ties to the mafia, famous mobster 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.

23. Summer Wind-Blocker

One of the unmistakable trademarks of Sinatra’s legendary swagger is his hat. Most people think of this singing icon as synonymous with the fedora—but believe it or not, hat enthusiasts would beg to differ. Technically speaking, Sinatra’s famous hat was not a fedora at all, but rather a trilby—a smaller brimmed hat intended for skinnier men, like Frank.

22. Start Spreading the News

Do you know Sinatra’s song “New York, New York”? While most of you probably answered “yes,” the correct answer should really be “which one?” More than 30 years before Ol’ Blue Eyes recorded what’s now considered New York City’s unofficial anthem, he performed another song with the very same name in the 1949 film On The Town.

21. Dream Team

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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20. Picky Eater

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

19. Neat Freak

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

18. Predecessor to Celine Dion

Sinatra actually made his lasting career in a Las Vegas residency.

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17. One More for the Roast

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. Roasted by the President? Not bad!

16. Under My Skin

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.

15. Fighting for the Cause

Fighting racism and discrimination was one of the issues 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. Through a series of incidents like this, Sinatra played a role in fighting Jim Crow laws in the United States.

 

14. That’s Life!

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.

13. Mistaken Identity

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.” I guess, when you think about it, “Rat Pack” isn’t exactly a flattering name.

12. Change of Heart

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.”

11. Friendly Fire

A madly jealous Sinatra partially blamed the downfall of his relationship with Ava Gardner on her inability to get over her former boyfriend and fellow Rat Packer, Peter Lawford. Sinatra once even 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. Gardner, on the other hand, blamed their divorce on Sinatra’s many affairs. Maybe you should have looked within instead of without, Frank.

10. A Funny Story

Sinatra’s fourth and final wife, Barbara, with whom he would remain married for 22 years until his death, was no stranger to Hollywood marriages—her first husband was Herbert “Zeppo” Marx, of the legendary Marx Brothers comedy team.

9. Frenemies

One of Sinatra’s closest political friendships of all time was with President John F. Kennedy. Sinatra was his 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.

8. Humble Beginnings

Sinatra’s performing career began modestly when he received a ukulele as a present from his uncle at age fifteen; he would use it to perform at family functions.

7. Literary Inspiration

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.

6. Match Made in Hell

Sinatra’s second marriage to movie star Ava Gardner was short-lived, widely publicized, and extremely turbulent. 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.

5. Cradle to the Grave

The world almost missed out on Frank Sinatra. The baby Sinatra was born blue and not breathing before doctors used forceps to forcefully yank him out of the womb by the head. They assumed that he didn’t make it, so they simply laid him on a table and began caring for his mother. This is when his grandmother took over and put young Frank under a cold water tap, causing him to immediately spring to life (I like to think singing “Summer Wind”). 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.

4. I’ll 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 a few weeks after the separation.

3. Unwanted Fan

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

2. Something Stupid

Sinatra and baseball star Joe Dimaggio once tried to raid their mutual ex-lover Marilyn Monroe’s apartment to catch her with another man, but accidentally raided the wrong place and invaded the home of a 39-year old secretary named Florence Kotz. Whoops!

1. Darkest Hour

In the early 1950s, 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 (future father of Star Wars star Carrie Fisher). 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.

Sources1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21

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