Credit: Associated Press/Indiana Gazette)

10 wild stories about Frank Sinatra

“Alcohol may be man’s worst enemy, but the bible says love your enemy.”

That’s Frank Sinatra for you. The ever-charming and witty personality who didn’t waste a single chance to entertain people. Undoubtedly the most influential artist of the 20th century, he glided smoothly through various professions gifting the world with unadulterated pleasure. He once said, “I would like to be remembered as a man who had a wonderful time living life…” and that’s precisely how we have remembered him.

Apart from being a power-packed performer, Sinatra was a sight for sore eyes. We’ll all probably agree that he was one of the most stylish celebrities who was always impeccably dressed in custom-tailored tuxedos and stylish pin-striped suits. His deep blue eyes which scored him the nickname “Ol’ Blue Eyes” and his magnetic persona were like sugar dust and cherry on the cake.

Sinatra wouldn’t have become Sinatra if it wasn’t for his wild antics. His wife, Barbra Sinatra wrote, “A big part of Frank’s thrill was the sense of danger that he exuded, an underlying, ever-present tension only those closest to him knew could be defused with humour.” Sinatra had extreme mood swings which ranged from violent attacks on journalists for writing bad reviews to overwhelming generosities such as buying Bobby Burns a Cadillac after fighting with him. His life is full of such insane stories that will shock people as well as make them giggle.

So, let’s take a look at the legend’s colourful life on his 105th birth anniversary.

The 10 rarely-told stories about Frank Sinatra:

10. The crazy time spent in Vegas

Sinatra turned to Las Vegas after his career stall in the 1950s and became one of its best-known residency performers. The intoxicating atmosphere of Vegas with its casino nights and champagne fountains furthered Sinatra’s inbred eccentricity.

In 1967, his gambling debt ran up to $500,000 at the Sands one night. Being sloshed, he then confiscated a golf cart and drove straight through the entry smashing the glass into pieces. It didn’t end there, he tried to light up the curtains with his Zippo lighter but thankfully failed to do so.

Sands Hotel marquee in 1959 featuring Frank Sinatra and Joey Bishop. (Credit: Wikimedia)

9. The Rat Pack and their casino orgies

Sinatra became a part of a swing band in Vegas, consisting of Dean Martin, Sammy Davis, Jr., Joey Bishop, and Peter Lawford known as the Rat Pack. Lauren Bacall coined the phrase referring to the Hollywood drinking circle where her then-husband and her future fling Sinatra were present. The hard-partying group was led by none other than Sinatra.

Being a Casanova, Sinatra allegedly ran a kind of private brothel during his stay in Vegas. He supposedly hosted after-hours orgies in a casino health club’s steam room for the band where he hired hookers and invited showgirls. In his 2013 memoir My Way, Paula Anka recalled that Sinatra’s only rule was “no gang bangs.”

Revisit the great Frank Sinatra performing The Beatles song 'Something' live
(Credit: Pixabay)

8. That time he starred in a porn movie

Who thought the famous icon’s filmography would contain something as wild as this. At the age of nineteen, Sinatra grabbed the opportunity to debut as an entertainer in the year 1935.

According to the 2011 biography Frank Sinatra: The Boudoir Singer, Sinatra was offered $100 to appear in The Masked Bandit, a porn film. Without any inhibition, he featured in the film wearing a mask. Though once he became an established artist, Sinatra tried his best to stop the blue film from surfacing by calling his friends in the mob.

(Credit: Metronome magazine)

7. His connection with the mafia world

Sinatra became the stereotype of the “tough working-class Italian American.” He once confessed that he would have ended up leading a life of crime if it wasn’t for his interest in music. In fact, his Godfather Willie Moretti was an underboss of the Genovese crime family. When Sinatra went to the Mafia Havana Conference in 1946, the press got an air of it and published news with the headings such as “Shame, Sinatra”.

Though he denied any such ties with the underworld by stating, “Any report that I fraternised with goons or racketeers is a vicious lie,” he was once almost caught helping the mafias. At the airport customs in New York Sinatra was found with a briefcase containing $3million in cash. The federal agents, however, had to let him go as fans started flooding in almost causing a riot.

Frank Sinatra with fans in Pasadena. (Credit: John T. Burns)

6. He couldn’t stand rock ‘n’ roll

For Sinatra rock ‘n’ roll music was “the most brutal, ugly, degenerate, vicious form of expression it has been my displeasure to hear.” He proceeded to take names and diss the genre and its musicians by calling The Doors song ‘Light My Fire’ one of the worst records he ever had heard.

Surprisingly, his list of favourite songs contained The Beatles’ ‘Something’ penned by George Harrison. He even covered the song in his initial live performances.

Sinatra hated rock music but had a soft spot for The Beatles. (Credit: Norman Parkinson)

5. He got sick of performing his popular numbers

While musicians get bored of performing popular numbers all the time, they generally keep that to themselves. Sinatra, outspoken as he was, couldn’t be expected to do that.

His signature anthem ‘My Way’, which originated as a French pop song, was re-written by Paula Anka for Sinatra in 1969. This version became a sensation and was soon covered by various musicians. However, Sinatra was very bitter about it. He once told the audience in Los Angeles “of course, the time comes now for the torturous moment not for you, but for me.”

Frank Sinatra and Harry James, 1943. (Credit: CBS)

4. His battles with obsessive-compulsive disorder

As with people having OCD Sinatra also shaved, brushed his teeth, gargled with mouthwash obsessively. While he was with Tommy Dorsey and his band, he got the nickname “Lady Macbeth” because of frequent showering and switching his outfits.

He even dabbed himself constantly with lavender water to mask the smell of cigarettes and whiskey.

Frank Sinatra and Ava Gardner. (Credit: IISG)

3. He hated his own album Strangers in the Night

Not all the work artists do is close to them. But the intensity with which Sinatra criticised and loathed some of his works is definitely unique.

Strangers in the Night was a 1966 studio album by Sinatra whose title track also released as a single. The album marked his return to number one rank in pop charts. As we have seen before, he was allergic of anything that became too popular and reportedly called his own work ” a piece of shit” and “the worst fucking song I’ve ever heard.”

(Credit: Reprise Records)

2. His violent side

Van Heusen said that when Sinatra got drunk, it was “best to disappear.” But as it appears, Sinatra could be equally violent when he was sober. During the 1960s he once paid a waiter $50 to punch writer Dominick Dunne in the face at an elite Hollywood restaurant. Another time, after arguing with a woman about politics, he summoned a valet to hit her with a plate of barbecued spareribs.

When the 50-year-old Sinatra married the 21-year-old Mia Farrow in 1966, it caused some stir. But Sinatra lost it when Farrow was humiliated publicly by Woody Allen’s relationship with her adopted daughter. He asked for Furrow’s permission to hire someone to break Allen’s legs.

Dean Martin, Judy Garland and Frank Sinatra, 1962. (Credit: CBS)

1. The JFK connection

Sinatra though held different views throughout his life, was always active in politics. Of all the U.S. Presidents he associated with during his career, he was closest to John F. Kennedy. Sinatra would often invite Kennedy to Vegas or Hollywood and enjoy parties together. In the 1960s, when Kennedy was running for the Democratic party, his dad supposedly asked Sinatra to get Sam Giancana, the mafia boss to deliver votes anyhow.

After Kennedy became the president, he cut off ties with Sinatra primarily because his brother Robert Kennedy, who was a lawyer, went after the mafia gang and convicted 288 mobsters in 1963. Sinatra, who was enraged by Kennedy’s betrayal smashed up the helipad which he had constructed on the roof of his anticipating Kennedy’s arrival, with a sledgehammer. He also changed his allegiance to the Republic party after this. Though he snubbed off JFK from his life, he allegedly cried in his bedroom for three days after his assassination.

Frank Sinatra as Tony Rome. (Credit: Wikimedia)
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