Over the course of American history, few pop culture icons carry the broad appeal of Ol’ Blue Eyes, Frank Sinatra. His songs. His movies. His style. He was not only cool, he was relevant for decades. But how well do you really know the Chairman of the Board?
Even today, Frank Sinatra has fans both old and young. The man seemed to attract every kind of person. After all, he hung out with both U.S. presidents and mobsters.
Let’s explore the most fascinating little known facts about the Sultan of Swoon.
He was unable to serve in WWII
Those who fought in the Second World War (and served on the home front) are known as “the Greatest Generation.” They were patriots who yearned to defend the United States at any cost.
Frank Sinatra was among them. Though he wasn’t permitted to fight.
It was rumored that Sinatra paid tens of thousands of dollars to evade the war. That proved untrue. The real reason was his perforated eardrum.
How does one suffer a perforated eardrum? Well, Frank’s birth was a harrowing one. Forceps were used to help deliver him (he was a 13.5-lb. baby!). The forceps damaged his cheek, neck and, yes, his eardrum.
He won an Oscar
With a voice like his, Sinatra was an otherworldly talent. Fortunately for us, he didn’t limit himself to the microphone. In the early to mid-1940s, he stepped in front of the camera.
As it turned out, he was a pretty good actor, too.
All his roles involved singing and dancing. Until 1953. That’s when he was cast as Italian-American GI Angelo Maggio in From Here to Eternity.
The World War II classic took home eight Oscars. And Frank was awarded one of them. His performance earned him the Best Supporting Actor prize. It also helped resurrect a slumping career.
Another legend inspired his career
Like most entertainers, Frank was influenced by those who paved the way. As a teenager, he took a liking to big band jazz. His favorite performer was, unsurprisingly, Bing Crosby.
For much of their careers, Frank and Bing would be associated with one another. And that’s not all.
In 1956, the two starred in a movie together, competing for Grace Kelly’s affections in High Society. It was one of the ten highest grossing movies that year and even garnered two Oscar nominations.
Sinatra and Crosby would then make a Christmas special a year later. It’s one thing to meet your idol; it’s quite another to surpass him.
He was frequently impersonated on Saturday Night Live
If you’ve been a big enough star between 1975 and present day, you probably got the parody treatment. And where better to be impersonated than on Saturday Night Live?
Sinatra, as a character, had a long run on the show. Two cast members portrayed him over the years.
From 1981 to 1984, Joe Piscopo played Frank. He did it in twelve sketches over that time. When Piscopo left SNL, so did the Sinatra character.
But in 1990, Phil Hartman stepped in, playing Frank in ten more sketches over the next six years. Both versions had Sinatra as hilariously gruff and unfiltered.
He made a film that won a special Academy Award
In 1945, Sinatra made a short film called The House I Live In. It features a group of boys chasing after another boy and berating him because he has a different religion than they do.
The outlier is, presumably, Jewish.
Sinatra then appears, teaching the kids a lesson about tolerance. After all, they’re all Americans, he argues. He then proceeds to sing the boys a cornball song.
The Academy gave him an Honorary Award for the short. When he was later accused of being a Communist sympathizer because of it, he said, “I don’t like Communists, and I have nothing against any organization except the Knights of Columbus.”
He was a movie combat pioneer
When we think of martial arts’ early days in cinema, people like Bruce Lee and Chuck Norris come to mind. There had been martial arts films in China long before those guys.
But American audiences were not accustomed to it. Until Frank Sinatra came along.
In 1962’s The Manchurian Candidate, Frank engages in a fight with actor Henry Silva. This is no table-breaking saloon fight. It’s two guys in a hotel room (in suits) throwing kicks and karate chops!
By today’s standards, it’s a bit stiff, but it sparked American interest in martial arts. Sinatra, by the way, broke his finger in the fight.
He had his own record label and film production company
It wasn’t smooth sailing all the time for The Voice, as he was known. Like most performers, he had his ups and downs.
Sinatra wasn’t too happy with Capitol/EMI. So, seeking more freedom in his work, he started his own label, Reprise Records.
It was through Reprise that Sinatra was given the nickname, the Chairman of the Board. These days, artists like Eric Clapton, Michael Bublé, and Josh Groban are signed to Reprise.
Because he was also a movie star, Sinatra founded his own independent film production company, too: Artanis (his last name spelled backwards). Two of his films and a TV movie were produced through Artanis.
He helped people who were struggling
Comedian Redd Foxx was no fan of paying taxes. The IRS on the other hand? Big taxes fans. So they took everything from Foxx, raiding both his home and his Los Angeles club.
Distraught, Foxx reached out to Sammy Davis Jr., who reached out to Sinatra.
Both Rat Pack members decided to help Foxx out. They performed at his club every night for a few weeks, selling out each show until Foxx had enough money to get his club back.
The two asked nothing in return. As for Foxx, did the wakeup call have an impact? Not at all. He’d continue his tax evasion for years to come!
A famous journalist might be his son
Frank has three children… that we know of. Son Frank Jr. and daughters Nancy and Tina all became singers and entertainers in their own right.
Then, in the late 2000s, Ronan Farrow introduced himself to the world. He’s the son of Mia Farrow and Woody Allen. Or is he?!
A journalist and author, Ronan helped break the 2017 Harvey Weinstein scandal. But he hasn’t been able to avoid questions about his DNA. Mia claims she and Frank never really split up, suggesting that he may be Ronan’s real father. See the resemblance?
While never confirming or denying this, Ronan joked, “Listen, we’re all *possibly* Frank Sinatra’s son.”
He attempted suicide
Even celebrities get down in the dumps sometimes. Frank was no stranger to that. In the early 1950s, his career had hit a snag. While in Times Square, he saw girls clamoring to see Eddie Fisher, not him.
So Frank went home and stuck his head in the oven.
Thankfully, his manager found him, alive and weeping on the floor. This wasn’t the only time Ol’ Blue Eyes tried to off himself.
He made three suicide attempts while married to Ava Gardner. On one occasion, he held a gun to his head, threatening to pull the trigger. She was able to wrestle the gun away, an errant shot firing.
A famous actress first called them the “Rat Pack”
Frank, Sammy Davis Jr., Dean Martin, Joey Bishop, and Peter Lawford made up the Rat Pack. At least the one most of us think of. Earlier versions consisted of other Hollywood stars, including Humphrey Bogart and Judy Garland.
They were known as the Holmby Hills Rat Pack. Thanks to Bogart’s wife.
Humphrey was married to actress Lauren Bacall until his death in 1957. She derogatorily identified Bogart and his buddies looking like a pack of rats upon their return home one night.
Sinatra and friends actually called themselves something else: “The Summit.” This was a play on the Paris Summit—a gathering of world leaders.
He threatened Woody Allen
No stranger to controversy, Sinatra often found himself the subject of many rumors. Namely, that he was part of the mob. Or at least friends with them.
If you like mafia films, you know that one thing those guys are good at is hurting people to send a message.
When Frank learned that Woody Allen had had an affair with adopted daughter Soon-Yi Previn, he offered to have Woody’s legs broken. At least according to Allen’s wife, and Frank’s ex, Mia Farrow.
But according to Woody’s biographer, Frank actually wanted Allen killed! He’d asked the mob, who felt the punishment didn’t fit the crime.
The strange “My Way” killings
Chalk this one up to… coincidence? Hopefully, anyway. “My Way” is one of Sinatra’s most beloved songs. It was actually a French song with lyrics re-written by Paul Anka.
Anka then pitched it to Frank, who recorded it in 1968. But that’s not the weird part.
Since 2000, up to a dozen people have been murdered in the Philippines just after—or during—a performance of “My Way.” In 2007, as a karaoke singer performed the song, he was shot dead by a security guard. The reason? He was singing it off key, the guard said.
The phenomenon has led to some bar owners refusing to play the song.
Bridging the gap
The Chairman of the Board wasn’t merely a singer and a movie star. He was also a film director. Under his Artanis Productions, Sinatra made his directorial debut in 1965.
The film was called None But the Brave. Most interesting about it was who he partnered with.
Joining Artanis was Toho Studios. The marriage of the two companies made the World War II movie the first Japanese/American co-production created in the United States. And it came just twenty years after the two nations were at war.
Critics weren’t crazy about it, but showing Americans the Japanese perspective hadn’t been done before.
He could have been the hero in Die Hard
Imagine Frank Sinatra as John McClane. Can you see him running around the Nakatomi Plaza with his shoes off, blowing away terrorists and delivering snappy one-liners?
Having a tough time replacing Bruce Willis with Frank? Well, it could have happened.
Die Hard is actually an adaptation of a novel by Roderick Thorp called Nothing Lasts Forever. The book was a sequel to Thorp’s 1966 novel, The Detective. The film adaptation (same title) stars Frank as Detective Joe Leland.
So Sinatra was given a right of first refusal for the sequel. He refused. Leland turned into McClane, and Die Hard was born. Yippee-Ki-Yay!
He was arrested for a surprising crime
When we think of Frank Sinatra, many things come to mind. His voice, his hats, his eyes. We also think of his bad boy reputation.
Sinatra had some trouble with the law as a young man. And it had nothing to do with the mob.
Frank certainly had a way with the ladies. Wives, girlfriends… others. In 1938, he was arrested in New Jersey. His mugshot has since become quite infamous. The charge? Seduction!
The woman he’d been arrested for seducing, it turned out, was married. So Frank was then charged with adultery! It didn’t take, however, and the case was dismissed.
His son was kidnapped
If you’ve watched enough movies, you know a great way to make a quick buck is a good old fashioned kidnapping. It helps if the person you hold for ransom is the child of a celebrity.
There’s big money in it, and it always works out. That’s what Barry Keenan and Joe Amsler thought anyway.
These two geniuses nabbed Frank Sinatra Jr. after he’d performed at a Lake Tahoe lodge. They took him to a secure location and demanded $240,000.
Unwilling to risk his son’s life, Frank Sr. gave the money to the FBI. The kidnappers were soon captured and the money was returned. Good try, guys.
The FBI watched him closely
Here comes that mafia rumor again. How could a sweetheart like Frank have any involvement with organized crime? Well, regardless of your opinion on the matter, there were others who believed the man was far from pure.
What began in the 1940s would last for decades.
The FBI’s watching him, that is. If they spied on Martin Luther King, why not Frank Sinatra? Over the years, the Bureau kept documents on Frank numbering in the thousands.
Whether it was his suspected involvement with the Communist Party or his many contacts who were under racketeering investigations, Sinatra was carefully looked at until 1985.
He wasn’t a Yankee fan
Perhaps no song is more closely associated with a sports team than Sinatra’s “New York, New York” is with the Yankees.
If you’ve ever been to Yankee Stadium or watched a Yankee home game on television, you heard the song blast through the park after the game ended.
Frank was a huge baseball fan. Most have assumed that his heart belonged to the Yankees. It would only make sense, considering the song.
But no. Frank grew up a New York Giants fan (before they moved to San Francisco). Later in life, when he relocated to Los Angeles, the Dodgers became his team.
He (probably) had comedian Jackie Mason beaten up
Comedian Jackie Mason is a Tony and Emmy award-winning performer ranked on Comedy Central’s greatest stand-ups ever.
He’s got fans all over the world. But there’s one guy he never appealed to. Yup, Frank Sinatra. Why not? Glad you asked.
In one of his acts, Mason made a joke at Sinatra’s expense. Apparently that’s something you just don’t do. And Mason found out the hard way.
He was later beat up and threatened in his hotel room by some gangsters for the dig he’d taken on stage. Mason was never able to confirm it was Frank who ordered the beating, but he thought it a safe assumption.
He didn’t start as a jazz singer
Sinatra is practically his own genre of music. His jazzy style has been copied over the years, but no one did it better than he did.
However, like many artists, it took some time for him to figure out his signature sound.
When he first broke out in the early 1940s, Frank was the lead singer of a vocal group called the Pied Pipers. They often accompanied big band act, the Tommy Dorsey Orchestra.
These performances earned Sinatra scores of adoring female fans called “bobby soxers.” They were predecessors to the sorts of crowds that Elvis Presley and the Beatles would later endure.
He wasn’t a model student
Though his talents were one of a kind, he wasn’t good at everything he attempted. One of Frank’s weak points was education.
Lots of artists have trouble staying focused in school. Their minds are preoccupied with their craft. But that’s not what plagued Ol’ Blue Eyes.
No, Sinatra had trouble behaving. Known for his explosive temper, he was prone to fights and other mischief. As a result, he was expelled from high school.
Ironically, a prestigious arts school in New York is still named after him—Frank Sinatra School of the Arts High School. What’s more, he’s got a building at Hebrew University in Jerusalem named after him as well!
Man of faith
Like many New Yorkers (and New Jersey-ers) of Italian descent, Frank grew up Catholic. He would abandon Catholicism in his adulthood, even becoming outspoken against organized religion.
But when he was advanced in age, Sinatra returned to his faith. So what sparked this?
On January 6th, 1977, Frank’s mother Dolly boarded a plane in Palm Springs. It would crash into a mountain, killing all four people on board.
Sinatra had a very difficult time coping with her sudden loss. As a result, he became a practicing Catholic again. He would remain in the church until his death in 1998.
A grief shared
The loss of Frank’s mother was a crushing blow. Curiously enough, a decade later, he was able to empathize with a good buddy in a particularly eerie way.
Frank and former Rat Pack member Dean Martin were linked again in 1987, but not how they wanted to be.
The 1977 plane crash that killed Dolly Sinatra happened on Mount San Gorgonio in California. Ten years and two months later, Dean Martin’s son, Dean Paul Martin, a Captain in the National Guard, was killed when his fighter jet went down.
Most bizarre about the crash: it happened on Mount San Gorgonio.
The Ava affair
Sinatra’s first wife was Nancy Barbato. The two were married from 1939 to 1951. Years before their relationship came to an end, Frank saw a photo in a magazine of actress Ava Gardner.
He made a promise to himself that he would marry that woman.
Apparently “Swoonatra” didn’t take his vows very seriously. At some point before he and Nancy’s divorce, Frank met Gardner in the flesh. An affair began.
When Nancy learned of it, she was done with him. As for Frank, he made good on his promise. He married Gardner that same year. Unfortunately, that marriage didn’t end well either.
A fighter against injustice
Sinatra was a man ahead of his time. Coming of age as World War II raged overseas, he made music unlike any other and would later extend an olive branch to Japan (through film, anyway).
He also loathed injustice. Discrimination and racism made his blood boil.
On one occasion, Frank insisted that singer Nat King Cole, a personal friend of his, join him in the dining room of a hotel. Here’s the kicker: it was a segregated hotel.
Sinatra even threatened to remove all his business from the hotel if anyone stood in the way of he and Cole.
He was wildly jealous
As many women as Sinatra romanced in his life, marrying the right one proved difficult for him. His relationship with Ava Gardner was rather volatile.
They divorced six years after they wed. She blamed their downfall on his many affairs. Frank had another version of the events.
He said that Gardner couldn’t get over her former boyfriend Peter Lawford. Lawford was, of course, another member of the Rat Pack. Sinatra burned with jealousy over this.
One night, he called Lawford and told him if he was ever seen with Ava again, Frank would send guys to break his legs. Seems reasonable enough.
He pulled one of his own movies from theaters for a bizarre reason
As famous as Sinatra is in the world of music, Lee Harvey Oswald may be his equal in the assassination industry. The two men have a deeper connection than you think.
And no, Frank wasn’t at all involved in that incident in Dallas… we don’t think.
Oswald had watched Sinatra’s film, Suddenly, just days prior to becoming the most famous man in America. Word is, he enjoyed the picture.
Well, when Frank heard that, he was none too pleased. He implored United Artists to completely remove Suddenly from circulation. Extreme, yes. But Sinatra wanted no association with that man and did whatever he could to prevent one.
Aside from “New York, New York,” La Voz (another of his nicknames) had one other connection to the New York Yankees.
And this one’s almost too good to be true. It involves not one, but three American icons in the same place. Well, almost.
Yankees slugger Joe DiMaggio, in addition to being one of the finest ballplayers who ever lived, was married for a time to the incomparable Marilyn Monroe. And Frank was once her lover.
One day, Sinatra and DiMaggio attempted to raid her apartment to catch her with another man. Turns out, they barged in on a secretary named Florence Kotz! Swing and a miss, guys!
His last performance
Frank died on May 14, 1998 at the age of eighty-two. He had performed up until early 1995. His swan song, it turned out, came on February 25th of that year.
About 1,200 people showed up to the Palm Desert Marriott Ballroom. Little did they know what they were in for.
It was the last night of a golf tournament at the hotel. Sadly, it would also be the very last time Sinatra sang before a crowd. His final song? “The Best is Yet to Come”
Appropriately, those are the same words found on Sinatra’s tombstone in nearby Cathedral City, CA.
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