Frank Sinatra: 12 Things You Never Knew About Ol’ Blue Eyes

by Jess Catcher
Jess grew up in Oklahoma before moving to New York to become a writer. She has a cat named Agnes.

It has been 19 years since legendary crooner Frank Sinatra passed away on May 14, 1998, but his memory remains alive and strong thanks to the many fans who still cherish his music and films.

Since releasing his debut album back in the 1940s, generation after generation has fallen for his smooth vocals and charming smile. It’s just impossible to deny Frank’s impressive catalogue of performances across the entertainment industry.

Frank was also no stranger to rumors and gossip in his day. However, I had no idea how much was really hiding under the surface of those piercing blue eyes, and for how many years.

Of course, nothing ever knocked “The Chairman of the Board” so far down that he couldn’t dust himself right back off again — not even as a baby, on the very day he was born.

Take a look to learn more about Frank Sinatra, and SHARE the surprising details about this incredible man’s life and career with your friends!

1. His Birth Was Quite Traumatic

frank sinatra as a baby

He was a hefty 13.5-pounds when his mother, Natalina “Dolly” Garaventa, endured a traumatic labor that forced the doctor to not-so-gently remove Frank with forceps. At first, he was blue and not breathing. The doctor believed he hadn’t survived and ignored him to tend to Dolly instead.

Luckily, his grandmother was also in the room and quickly stuck him under cold water, which revived the infant. Frank also suffered injuries from the forceps, including a punctured eardrum that remained that way for the rest of his life.

2. He Was Bullied At School

young frank sinatra with hoboken four

Those forceps also left scars across the left side of his face, along his mouth and jawline. That, in addition to a bout of particularly awful cystic acne, earned young Frank the nickname “Scarface” from his more cruel peers.

3. He Was Arrested For Being Too Amorous

young frank sinatra at rustic cabin

How did he end up with a mugshot?

In 1938, Frank was working as a singing waiter at roadhouse bar called the Rustic Cabin, shown above. It was there that he ran into trouble with the law after he indulged in relations with a woman who turned out to be married. He was first charged with “seduction,” which claimed he wooed her “under the promise of marriage.”

His bail was set at $1,500, but when the authorities discovered the woman had a husband, the charge was lowered to “adultery,” and the amount was lowered to $500 before being dropped entirely.

4. His Early Fans Were Paid To Scream

young frank sinatra

While getting his start in the beginning of the 1940s, his publicist George Evans wanted to make sure his shows created quite a frenzy. To ensure this, he offered 20 girls in attendance $5 each. The terms? They had to occasionally whip up the excitement by screaming ecstatically.

Not a bad gig for the girls, considering $5 was the equivalent of about $75 today!

5. His Lengthy FBI File Started In 1943

frank sinatra recording

Long before rumors of mob affiliations began swirling around the crooner, his massive popularity caught J. Edgar Hoover’s attention and inspired suspicions regarding the power he could wield over “hysterical” fans.

The file also accuses Frank of having paid $40,000 for a doctor to get him out of being drafted during World War II.

6. A Short Film Got Him In Hot Water

frank sinatra filming

In 1945, Frank played a fictionalized version of himself in The House I Live In. In it, his character lectures a group of young boys for bullying a Jewish boy. He points out to them that they were all Americans, regardless of their race or religion.

Ironically, the uplifting message later caused him and those associated with film to be labeled “communist sympathizers” during the investigations by Senator Joe McCarthy and the House Un-American Activities Committee.

7. He Struggled With Depression

frank sinatra recording

Despite the air of confidence Frank always put on display in public, he secretly battled intense inner demons and even made attempts to take his own life — at least three times.

8. He Had A Feud With Marlon Brando

marlon brando

Tensions were high when the pair were cast alongside each other for the film adaptation of Guys and Dolls.

Frank was jealous of Marlon snagging the more prominent role despite having less experience as a singer. Among their many arguments on set, Marlon would also taunt him by purposely flubbing his lines in the scene where Frank’s character was eating cheesecake — knowing how much the singer hated the dessert — forcing him to eat slices until he felt sick.

9. There Is An Asteroid Named After Him

sinatra asteroid

The celestial rock was discovered by Belgian astronomer Eric Walter Elst in 1989 and officially dubbed “7934 Sinatra.”

10. He Tried To Sell Pasta Sauce

frank sinatra

Using the recipe passed down by his mother, Frank’s sauce lined grocery store shelves back in 1990, under the name Artanis (his last name spelled backwards). It ultimately failed to find the same success as his contemporary Paul Newman’s line of food items.

11. His Duet With Nancy Made Chart-Topping History

frank and nancy sinatra

In 1967, their version of “Something Stupid” became the first (and remains the only) father-daughter duet to ever reach number one spot on the Billboard Hot 100 charts.

12. He Was Buried With A Few Of His Favorite Things

frank sinatra

According to a book that takes a closer look at celebrity deaths, Frank’s loved ones gave him final gifts at his funeral, including bourbon, cigarettes, a roll of dimes to call his friends and family from heaven, a dog treat to feed any pups he might find up there, and his favorite candy: Tootsie Rolls.

Did you learn something new about Ol’ Blue Eyes?

Be sure to SHARE all these fascinating Frank Sinatra facts with your friends!