The Life and Times of Frank Sinatra: How a Legend Became His Own Worst Enemy

Does anyone here NOT know who Frank Sinatra is? Yeah, I didn’t think so. The whole world knows of Frank Sinatra, millions were real fans who listened to his music, and many saw his movies. But how many people know what his personal life was really like? How many people know that he had four wives, had the FBI following him for 40 years and that his son was kidnapped? And that’s just to name a few.

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The talented singer and actor with nicknames like The Voice and Ol’ Blue Eyes was basically America’s first teen idol. The crooner could make bobby-soxers faint, became an Academy Award-winning actor, and a pioneer of Las Vegas resident performers. But for Frank Sinatra, with the money and fame came turmoil. The man basically became his own enemy. See why…

This is the true and fascinating story of Frank Sinatra, a legend in the making.

It Started With a Traumatic Birth

Francis Albert Sinatra was born on December 12, 1915, in an apartment (at 415 Monroe Street) in Hoboken, New Jersey. He was the only child of Italian immigrants Natalina “Dolly” Garaventa and Antonino Martino “Marty” Sinatra. He had to be delivered with the aid of forceps, and he came out blue and not breathing.

Photo By Kobal/Shutterstock

Believe it or not, they thought the baby was stillborn and even laid him on the kitchen counter while the doctor attended to his mother. His grandmother went to pick up the newborn, held him under some cold water, and the tiny little Frank wailed out his first-ever tune. The future crooner, by the way, weighed a whopping 13.5 pounds. And those forceps left their mark on Sinatra’s face, leaving him with more than just a physical scar…

He Was Called “Scarface”

Those forceps caused severe scarring to Frank’s left cheek, neck, and ear, and even punctured his eardrum – damage that lasted a lifetime. Frank’s scar ran from the corner of his mouth to his jaw line and ear. A childhood operation done on his mastoid bone left major scarring on his neck. Pair that with the cystic acne that he suffered from during his adolescence, and you can understand where his nickname came from.

Frank Sinatra.
Photo By MGM/Kobal/Shutterstock

In his teen years, Frank was nicknamed “Scarface.” He was so self-conscious of his looks that he often applied makeup to hide the scars on his face. Even during his adult years and with the makeup applied, he still hated to be photographed on his left side. His physical insecurities didn’t end there either; Sinatra wore “elevator” shoes to boost his five-foot-seven height.

Marty and Dolly Sinatra

Sinatra’s biographers believe that his mother, Dolly, was the dominant factor in the development of his personality and self-confidence. According to Frank’s fourth wife, Barbara Marx Sinatra, Dolly was abusive to him as a child, and apparently “knocked him around a lot.” Dolly was energetic and driven and became influential in the town of Hoboken and in the local Democratic Party circles.

Ronald Reagan, Nancy Reagan, Mrs. Martin Anthony Sinatra, Frank Sinatra
Governor Ronald Reagan, Nancy Reagan, Vice President Spiro Agnew, hospital director Glen Bailey, Mrs. Martin Anthony Sinatra, Frank Sinatra at the opening of Palm Springs Desert Hospital, 1/15/71 Photo By Everett Collection/Shutterstock

Dolly worked as a midwife, earning $50 for each delivery, and allegedly ran an illegal abortion service for Italian Catholic girls (she was nicknamed “Hatpin Dolly”). While she had a gift for languages, Frank’s father, Marty, was illiterate. He was a bantamweight boxer who fought under the name Marty O’Brien. He also worked for the Hoboken Fire Department for 24 years.

The Best Dressed Kid on the Block

Frank spent a lot of his early years at his parents’ tavern in Hoboken, doing his homework and sometimes singing a tune on top of the piano music for spare change. The Sinatras weren’t poor by any means, though. During the Great Depression, Dolly gave her son money when he would go out with friends and to buy expensive clothes.

Photo By Globe Photos/Shutterstock

His neighbors described Frank as the “best-dressed kid in the neighborhood.” But Frank was excessively thin and small, and his skinny frame later became a staple of jokes during many stage shows. Despite all that, Sinatra was still known for his immaculate sense of style. He spent loads of money on custom-tailored tuxedos and pin-striped suits, which made him feel rich and important.

An Ear for Music

Sinatra had developed an interest in music at a young age, with a particular fondness for big band jazz. He listened to Gene Austin, Russ Colombo, Rudy Vallée, Bob Eberly, and he idolized Bing Crosby. Frank’s uncle, Domenico, gave him a ukulele for his 15th birthday, and the teenaged Frank would perform at family gatherings.

Bing Crosby
Bing Crosby. Photo By Otto Dyar/Kobal/Shutterstock

Sinatra went to A. J. Demarest High School (since renamed Hoboken High School) where he would arrange bands for the school dances. But Sinatra never graduated high school, having gone for only 47 days before finally being expelled for “general rowdiness.” To please his mother (something he always strived to do), he enrolled at Drake Business School only to leave after 11 months. School wasn’t for him, which is why he resorted to doing odd jobs to get by…

Finding His Voice

Dolly found Frank a job as a delivery boy for the Jersey Observer newspaper. After that, Sinatra was a riveter at the Tietjen and Lang shipyard. He would also perform in Hoboken’s local social clubs like The Cat’s Meow and The Comedy Club. He sang for free on radio stations like Jersey’s WAAT. It got to the point that Frank Sinatra was learning that his voice was his skill.

Frank Sinatra and Cuban orchestra leader Noro Morales
New York, New York: 1944 Frank Sinatra takes a break from dancing at the Stork Club to chat with Cuban orchestra leader Noro Morales. Photo By Underwood Archives/Shutterstock

His voice became a means to an end – a way to make money. And when he got to New York City, Sinatra found jobs singing for his dinner or even for cigarettes. But singing wasn’t the only thing he cared about. He wanted to improve his speech, so he took pronunciation lessons for a dollar each from vocal coach John Quinlan. John was the first person to notice his impressive vocal range.

From The 3 Flashes to the Hoboken Four

Sinatra began singing professionally when he was a teenager, but he never learned to read music, having learned it all by ear. It was in 1935 that he got his first break. His mother convinced a local singing group called The 3 Flashes to let him join. Fred Tamburro (the group’s baritone) said that “Frank hung around us like we were gods or something.”

the Hoboken Four

Tamburro later admitted that they only let Frank in because he owned a car, and he could chauffeur them around. When Frank learned that they were auditioning for the Major Bowes Amateur Hour, he begged the group to let him in on the act. With Sinatra, the group then became the Hoboken Four. They got the Major Bowes gig and each member earned $12.50 for the appearance.

The Road to Success Began

That appearance on the Major Bowes Amateur Hour show was the beginning of a promising career for the young, skinny, and talented kid. Their performance attracted 40,000 votes and won first prize, which was a 6-month contract to perform on stage and on the radio across the United States. It didn’t take long for Frank to become the group’s lead singer.

Teenage girls waiting for singer Frank Sinatra to arrive at the Paramount Theatre. 1945 in New York City.
Photo By Everett Collection/Shutterstock

And yes, it’s safe to say that the other three members were envious of Frank getting all the attention, especially from the girls. A few years later, in 1938, Sinatra found a job as a singing waiter at a roadhouse called “The Rustic Cabin” in Englewood Cliffs, New Jersey. That gig paid him $15 a week. It was in 1938 that he got arrested…

The Famous Mug Shot

Sinatra’s bad boy image was real, and it all began with his infamous 1938 mug shot. Do you know what he was even charged for? Well, the charge was for what we can say is the most “Frank Sinatra reason” ever: seduction. He was arrested by the Bergen County (New Jersey) sheriff and charged with carrying on with a married woman (aka adultery).

Frank Sinatra was arrested by the Bergen County, New Jersey sheriff in 1938 and charged with carrying on with a married woman. The charge was later changed to adultery and eventually dismissed. Source: Shutterstock

The charge was later changed to adultery but was eventually dismissed. So, who was the married woman that caused him to take one of the most famous mug shots ever? Nancy Sinatra. Well, she wasn’t a Sinatra at that point; she was Nancy Barbato back then. Anyway, she eventually left her husband and married Frank. Nancy became frank’s first (of four) wives.

When Frank Met Nancy

As it turns out, Sinatra had a thing for married women. He had several extramarital affairs, including ones with Marilyn Maxwell, Lana Turner, and Joi Lansing. But Nancy was the apple of his eye, at least for a while. He met her in Long Branch, New Jersey in the late 30s when he was 19 years old. It was during a time when he spent most of the summers working as a lifeguard. Remember, he was still a teenager at that time.

Frank Sinatra Jr, Nancy Sinatra Jr, Frank Sinatra
Frank Sinatra Jr, Nancy Sinatra Jr, Frank Sinatra in 1948. Photo By Snap/Shutterstock

It was after the “incident” at The Rustic Cabin (that led to his arrest) he married Nancy on February 4, 1939. Frank and Nancy had two children who they decided to name after themselves. Tina Sinatra became a singer; Nancy, as we all know, became a famous singer, too. And even Frank Jr. tried his hand at singing and was even kidnapped (which we’ll get to later).

His First Record Was in 1939

In 1939, Frank was performing with a group during a ‘Dance Parade’ show. And despite the low salary, he felt that this was definitely the break he was looking for, bragging to friends that he was going to “become so big that no one could ever touch him.” Harry James heard Sinatra sing on the Dance Parade show and signed Frank to a two-year contract of $75 a week.

Frank Sinatra, Nancy Sinatra
Photo By Kobal/Shutterstock

It was with the James band that Frank released his first commercial record called “From the Bottom of My Heart” in July of 1939. About 8,000 copies of the record were sold, but this was just the beginning. Thanks to his vocal training, he was now able to sing two tones higher, and was making more records, like “My Buddy,” “Willow Weep for Me,” “It’s Funny to Everyone but Me,” “Here Comes the Night,” “On a Little Street in Singapore,” and “Every Day of My Life.”

Frustrated and Ready to Move On

Sinatra became increasingly frustrated with the Harry James band, feeling that he wasn’t getting the kind of success he was looking for. The band’s pianist and his close friend Hank Sanicola convinced him to stay with the group. But by November 1939, Frank left the group to become the lead singer of the Tommy Dorsey band (replacing Jack Leonard). With the new band, Sinatra earned $125 a week, appearing at the Palmer House in Chicago.

Tommy Dorsey, Frank Sinatra
Tommy Dorsey, Frank Sinatra. Photo By Paramount/Kobal/Shutterstock

Frank Sinatra’s first public appearance was on January 26, 1940, with the Dorsey band at the Coronado Theatre in Rockford, Illinois. Dorsey later recalled: “You could almost feel the excitement coming up out of the crowds when the kid stood up to sing. Remember, he was no matinée idol. He was just a skinny kid with big ears. I used to stand there so amazed I’d almost forget to take my own solos.”

He Was One of America’s First Teen Idols

In the 1940s, Frank (or Frankie as he was then known) became one of America’s first teen idols. By 1941, Sinatra was a hit and was named Billboard’s Top Male Vocalist. He was the new “It” boy. But let’s don’t forget that he still saw himself as the “ugly” skinny kid. Sinatra later recalled a series of shows he did in 1942 at New York City’s Paramount Theater, that “The sound that greeted me was absolutely deafening. I was scared stiff. I couldn’t move a muscle.”

Bobby Soxer fans eagerly waiting to see Frank Sinatra outside the Paramount Theater. New York City, Oct. 12, 1944.
Bobby Soxer fans eagerly waiting to see Frank Sinatra outside the Paramount Theater. New York City, Oct. 12, 1944. Photo By Everett Collection/Shutterstock

Did you know that some of his screaming fans were paid? Not to take anything away from his talent and ability to wow audiences, but the bobbysoxer craze (due to the coed fans who wore Catholic school-style bobby socks) had a little unorthodox help. George Evans, Sinatra’s publicist, would audition girls for how loud they could scream. He paid five bucks and placed them strategically in different parts of the audience.

Tommy Dorsey Was Like a Father to Him

During his first year with the Dorsey band, Sinatra recorded over 40 songs. As his success and popularity grew, Frank begged Dorsey to let him record some solo songs. Dorsey gave in, and by January 1942, Sinatra recorded songs like “Night and Day,” “The Night We Called It a Day,” and “The Song is You.” After those 1942 recordings, Sinatra was convinced that he needed to go solo.

Tommy Dorsey, Frank Sinatra
Source: Pinterest

But Dorsey was a major influence on Sinatra, who saw him as a father figure. Sinatra would mimic Dorsey’s mannerisms and traits, becoming a perfectionist like him, and even adopted his hobby of toy trains. Sinatra later said how “The only two people I’ve ever been afraid of are my mother and Tommy Dorsey.”

Going Solo Came With Some Problems

In 1942, Frank wanted to go solo, but he was restricted by his contract with Dorsey, in which he had to give Dorsey 43% of his lifetime earnings in the entertainment industry. A legal battle went down, and they eventually settled in August 1943, but by 1942 Sinatra had stopped singing with the band. In September 1942, Dorsey said farewell to Sinatra, saying, “I hope you fall on your ass.” Their loving relationship had gone sour.

Frank Sinatra - 1942
Frank Sinatra – 1942. Photo By Rca/Kobal/Shutterstock

It was during this period that Frank’s ties to the mafia became apparent. Rumors started spreading in newspapers that Sinatra’s mob “godfather,” Willie Moretti, forced Dorsey to let Sinatra out of his contract while holding a gun to his head. Dorsey occasionally made harsh comments to the press, like “he’s the most fascinating man in the world, but don’t put your hand in the cage.” Dorsey and Sinatra never reconciled their differences by the time Dorsey died in 1956.

From Hollywood to Vegas

Sinatra tried to pursue an acting career in the early 1940s. And while films appealed to him, he was rarely enthusiastic about his acting, once saying that his “pictures stink.” His film debut was in an uncredited sequence in ‘Las Vegas Nights’ (1941), singing the song “I’ll Never Smile Again.” By the early 1950s, Sinatra’s professional career had stalled for a bit, and having felt rejected by Hollywood, he turned to Las Vegas.

Charity, Ed “Archie” Gardner, Danny Kaye, Frank Sinatra, Red Skelton in 1947. Photo By Snap/Shutterstock

It was in Vegas that he became one of the best-known residency performers as part of the Rat Pack. His debut was at the Desert Inn in 1951. He eventually became one of Las Vegas’s pioneer residency entertainers and a major figure on the strip throughout the 50s and 60s. The Rat Pack provided Sinatra with an outlet for expressive banter and wisecracks.

Why the FBI Followed Him for 40 Years

Okay, so I mentioned his ties to the mafia, which only means that now I have to talk about the part of Sinatra’s life that has to do with the mafia. Apparently, the FBI had been documenting his every move for about 40 years. It looks like his fans and critics weren’t the only people who wanted a piece of ‘Old Blue Eyes.’ The FBI was just as interested, just for different reasons.

Frank Sinatra signs his induction papers
Frank Sinatra signs his induction papers while Chief Clerk Mrs. Mae E. Jones helps out at local board No. 19-160 in Jersey City. Sinatra was exempted from military service due to a perforated eardrum. Photo By Everett Collection/Shutterstock

The FBI tracked Sinatra for decades, collecting a record of thousands of pages regarding his movements, words, and friendships. The files were made public after Sinatra’s death in 1998. It was during his rise to fame in the 40s that Frank attracted the attention of the FBI. It started when there were claims made of him paying a doctor $40,000 to declare him medically unfit for service in World War II.

Not Acceptable For Military Service

Sinatra never served in the military during World War II. On December 11, 1943 (at the age of 28), he was officially classified as “Not acceptable for military service” by his draft board due to his perforated eardrum. But according to U.S. Army files, Sinatra was “not acceptable material from a psychiatric viewpoint.”

Gene Kelly, Frank Sinatra
Gene Kelly, Frank Sinatra. Anchors Aweigh – 1945. Photo By MGM/Kobal/Shutterstock

But this emotional instability was hidden to avoid “undue unpleasantness for both the selectee and the induction service.” Even though the FBI dismissed the allegations of him paying to get out of the service, the rumor still persisted throughout his lifetime and even hurt his career in the late 40s. His excuse for not serving was watertight, but his ties to known Mafia members weren’t as squeaky clean.

He Denied His Connections to the Mob

Sinatra’s FBI file was like a guide to the era’s organized crime figures, but Sinatra continued to deny that he had any connections to the mob. He did, however, interact with Mafiosos, like Chicago mob boss Sam Giancana, who was a close friend of his. Sinatra supposedly introduced Giancana in 1960 to John F. Kennedy‘s campaign in an attempt to deliver union votes to the soon-to-be president.

Sam Giancana and Frank Sinatra
Sam Giancana and Frank Sinatra. Source: Pinterest

According to Tina Sinatra, her father played a gig at Giancana’s club in Chicago to repay the favor. Sinatra then introduced Kennedy to Judith Campbell Exner, who was Giancana’s girlfriend. During a years-long affair that followed that, Exner acted as a liaison between Kennedy and Giancana. Those ties were said to help in the plot for the Mob to assassinate Fidel Castro. But it never did in the end.

He Offered to Snitch on Them

Sinatra was proud of his friendships with people in the mafia and took tons of public photographs with known mobsters. He and his gangster friends shared similar passions – gambling, women, money – and they would meet in casinos and nightclubs. But it came to a point in time when Sinatra offered to snitch on some of the criminals he knew.

Frank Sinatra, John Kennedy
Frank Sinatra, John Kennedy. Photo By Moviestore Collection/Shutterstock

In 1950, Sinatra sent an associate to J. Edgar Hoover to offer to be an informant, perhaps to protect himself from rumors that he was involved with the Mob. But the FBI declined. Hoover’s aide wrote: “We want nothing to do with him.” Sinatra was never arrested for criminal behavior in connection to his Mob ties. The FBI didn’t focus only on the singer himself. Sinatra was such a high-profile star that he was regularly targeted for extortion or blackmail him.

Which brings us to his son’s kidnapping…

The Failed Kidnapping of Frank Sinatra Jr.

In 1963, things got all too personal when three men kidnapped Sinatra’s son, then 19-year old Frank Jr. Just two weeks after JFK was shot, Sinatra’s son was taken, hostage. On paper, the plan was thought out. But Barry Keenan, Joe Amsler, and John Irwin, who were former classmates of Frank Jr.’s older sister, got in over their heads. And it actually reads like a scene from a movie. But this really happened, folks.

Frank Sinatra Jr., (center), with his mother, Nancy Sinatra
S Frank Sinatra Jr. (center), with his mother Nancy Sinatra next to him, after his father (Frank Sinatra), paid a ransom of 240,000 dollars to kidnappers to release him, December 11, 1963. Photo By Everett Collection/Shutterstock

They arranged to kidnap the famous star’s son and hold him hostage for ransom money. The boys later admitted that they even considered kidnapping Bob Hope’s son, but chose not to as it would be “un-American.” They figured Frank Jr. was a better bet, and given his father’s history, it “wouldn’t be morally wrong” to make him suffer for a few hours.

But that was the plan. In execution, the plan went south…

The Kidnapping Didn’t Go as Planned

It started going downhill when during the kidnapping, the boys let the one witness to the abduction go free. Frank Jr. was at the Harrah’s Club Lodge in Lake Tahoe, and he was sitting in his dressing room with a friend at the time when he was abducted. Keenan and Amsler tied up Jr.’s friend with adhesive medical tape and blindfolded him before taking Jr. to their car.

Frank Sinatra Jr.
Photo By Everett Collection/Shutterstock

Within minutes, Jr.’s friend freed himself and called the cops. The FBI was brought in, and after getting a description of the car, they put roadblocks on the roads, but the kidnappers were long gone. The boys’ next mistake was when they made the ransom demand. Even though Sinatra offered them a $1 million reward for his son’s safe return, Irwin (who was in charge of orchestrating the ransom), only asked for $240,000.

The Three Stooges

At that point, the cops were aware that the kidnappers were clearly not seasoned pros. They advised the Sinatra family to pay the $240,000, as it would likely lead them to the kidnappers. Photos were taken of the money before it was dropped at the designated site, which was a Texaco gas station in Sepulveda, California. And then there was the third, and possibly most laughable slipup.

Barry Keenan (L), Joe Amsler (Center), John Irwin (R)
Barry Keenan (L), Joe Amsler (Center), John Irwin (R). Source: FBI,gov

The kidnappers intended to hold Jr. hostage for as long as it took to get the money, and possibly even longer, but in the end, he was released after just over two days. When Keenan and Amsler went to pick up the cash from the Texaco station, Irwin got nervous. Instead of waiting for the other two to come back with the money, he let Frank Jr. go free.

One of the Most Ridiculous Cases Ever

While Frank Jr. was picked up a few miles away in Bel Air, Irwin fessed up to his brother, who called the FBI. They located Keenan and Amsler just a few hours later, in possession of the ransom money. All three boys were convicted of kidnapping. In the end, the courts ruled that the kidnapping was simply a poorly-executed brainchild of three resentful students, looking for a spot in the limelight.

suitcase used for the cash provided by the Sinatra family
Kidnappers demanded a ransom of $240,000 for Frank Sinatra, Jr. Agents used this suitcase for the cash provided by the Sinatra family. Source: FBI,gov

The case could have ended in tragedy, but it ended up turning into a media frenzy and went down in history as one of the most famous, and equally ridiculous, kidnapping cases ever.

Meanwhile, Sinatra knew the government was tracking his activities. By 1979, he requested and received his FBI file (through the Freedom of Information Act). His file never ended up getting him in trouble, but it did include things not relating to the mob that some might find amusing. For example, the file begins with a letter that complains about the “shrill whistling sound” that came from Sinatra’s fans.

Sinatra Was His Own Worst Enemy

J. Randy Taraborrelli updated his biography on Frank Sinatra, revealing some new details on the star’s suicide attempts, love affairs, and failed marriages. As it turns out, Frank was tormented by his own inability to find love. When he and Nancy moved to Hollywood, he strayed from his marriage into extra-marital affairs, starting with actress Marilyn Maxwell. His affairs became public knowledge and it greatly embarrassed Nancy.

Ava Gardner, Frank Sinatra
Photo By Moviestore Collection/Shutterstock

Nancy and Frank announced their separation on Valentine’s Day in 1950, while Frank’s other affair with actress Ava Gardner became public knowledge. By 1951, Frank and Nancy were divorced, and Sinatra’s relationship with Gardner became more serious, which led to her becoming his second wife. She was married to him from 1951 until 1957.

His Marriage to Ava Gardner

According to Ruth Rosenthal, a friend of Ava Gardner’s, Ava initially hate Frank when she met him at MGM Studios. She thought he was “conceited, arrogant, and overpowering.” But they had a lot in common: they both smoked, drank, cursed, and loved violent sports. But this relationship was rocky from the beginning and uneven, as Frank was the one who loved her more than she loved him. “She pitied him more than she loved him,” Sinatra’s friend Sammy Davis Jr. said.

Ava Gardner, Frank Sinatra. marriage
Photo By Snap/Shutterstock

According to biographer J. Randy Taraborrelli, “She treated him cruelly, the way he’d treated every woman before, and it humbled him. Frank was devastated.” It was during their marriage that Sinatra made his third suicide attempt. Ava walked into the bedroom to find Frank seated on the bed, holding a gun to his head. As she tried to wrestle the gun away, a shot fired, but miraculously the bullet missed them both and hit the bedroom door.

Frank’s Suffering Was a Secret

The extent to which Frank Sinatra suffered was hidden until Taraborrelli exposed it in his updated biography, “Sinatra: Behind the Legend.” The book came out only months before the 82-year-old Frank’s death in 1998. There were now never before heard interviews with Frank’s friends, family members, and lovers who never spoke until he passed away. Frank described himself as “an 18-carat manic depressive.”

Lauren Bacall, Frank Sinatra
Lauren Bacall, Frank Sinatra. Photo By Kobal/Shutterstock

According to Taraborrelli, “he was a bipolar, moody, difficult man who drank heavily, with a sense of entitlement twisted by celebrity.” Sheer talent and fame aside, he was a womanizer, getting involved with women like Marilyn Monroe, Lauren Bacall, Lana Turner, and Jacqueline Kennedy. His problem was that he was never happy. “He always thought there was something better just around the corner.”

A Hard Fall

Gardner filed for divorce in 1954, but the divorce wasn’t settled until 1957. Sinatra blamed Peter Lawford (who had dated Gardner before) for their breakup, and it took Sinatra six years to forgive him. His divorce to Gardner devastated him, and his friend Jimmy Van Heusen even found him in the elevator of his New York City apartment with his wrists slashed.

Frank Sinatra and Donna Reed
1953 the 26th Academy Awards Frank Sinatra and Donna Reed Won Oscars For Their Supporting Roles in ‘From Here to Eternity.’ Photo By Globe Photos/Mediapunch/Shutterstock

Her power in Hollywood actually helped Sinatra get cast in the film ‘From Here to Eternity,’ and his Academy Award for Best Supporting Actor is what revitalized his film career. But their split had a profound impact on him, the songs he sang, and even on his voice. He would console himself in songs like “I’m a Fool to Want You,” “Don’t Worry ‘Bout Me,” and “There Will Never Be Another You.”

Long after their split, Sinatra was still dealing with Gardner’s finances in 1976. He even paid $50,000 for her medical bills.

Trying to Move On

His stormy marriage to Ava Gardner lasted six years. Sinatra perpetually sought love in the arms of a new woman. Sinatra then met and started a relationship with Lauren Bacall, who fell for Sinatra after the death of her husband Humphrey Bogart in 1957. Sinatra and Bacall were seen together a lot in public throughout 1957, and by 1958, they were engaged. But apparently, Sinatra denied ever intending to marry her.

Frank Sinatra, Lauren Bacall. 1957
Frank Sinatra, Lauren Bacall. 1957. Photo By Kobal/Shutterstock

During a secret engagement, Sinatra got cold feet and broke off their engagement without even telling Bacall. “He didn’t return her calls, didn’t tell her it was over,” Taraborrelli said. “It was cruel, sending her into a spiral of depression.” He had a pattern on shamelessly dumping women, as he did with the one and only Marilyn Monroe.

He Almost Married Marilyn Monroe

Frank met Marilyn in 1954 (while he was still married to Ava Gardner) as he was friends with Marilyn’s second husband Joe DiMaggio. But the two met again in 1961 and began an affair with her. Monroe had spoken about marrying Sinatra, but he broke things off later that year (around the same time he was seeing the actress and dancer Juliet Prowse).

Photo By Moviestore Collection/Shutterstock / Globe Photos/Shutterstock

Sinatra’s fling with Monroe occurred a year before her death from a drug overdose in 1962. During their relationship, Frank’s friends convinced him that he would be the one to blame if the famously unstable actress killed herself while married to him. Marilyn was also brutally dumped by Sinatra. The list of women in Sinatra’s life goes on and on, but we can move on to his third wife…

His Controversial Marriage to Mia Farrow

When Frank was 48 years old, he met 19-year-old Mia Farrow on a movie set. He was smitten. He told his close friend Dean Martin: “I’m tired of feeling sad, old and washed-up. We’re talking marriage already.” Dean told him, “Martin gasped: “Jesus Christ, Frank, I got Scotch older than this kid.” Farrow’s mother, actress Maureen O’Sullivan, also had something to say of their controversial relationship. “He’s having a mid-life crisis, but why can’t he get hair plugs and a sports car-like other men?”

Frank Sinatra, Frank Sinatra, Mia Farrow
Frank Sinatra, Frank Sinatra, Mia Farrow. Photo By Moviestore Collection/Shutterstock

Frank and Mia got married in 1966, but their marriage was a hell of a lot shorter than his previous two. After only 16 months, Farrow refused to abandon the movie that eventually made her, ‘Rosemary’s Baby,’ to appear in a forgettable film with her husband. Frank then filed for divorce.

Fourth Time’s a Charm

Frank swore off of famous actresses and moved on. He eventually met and married Barbara Marx, the former Las Vegas showgirl and ex-wife of Zeppo Marx. Barbara must have been smitten with the crooner because converted to Catholicism to marry him. The two were in love, but that didn’t stop him from demanding that Barbara sign a prenuptial agreement three days before their 1976 wedding, saying that if she doesn’t sign it, he would walk away.

Frank Sinatra and Wife Barbara Marx. 1976
Frank Sinatra and Wife Barbara Marx. 1976. Photo By Nate Cutler/Shutterstock

In Sinatra’s life, the fourth time’s a charm because she remained his wife up until his death. That doesn’t mean that everything was rosy, though. Apparently, her relationship with Sinatra’s children were consistently stormy – something Nancy Sinatra confirmed. Nancy claimed that Barbara didn’t even bother to call Frank’s children when the end of his life was near (even though they were close by), and thus his children missed the opportunity to be at their father’s side when he died.

Mr. Mumbles and Mr. Baldy

Sinatra had a preference for approaching movie roles in a spontaneous (rather than rehearsed) way, which earned him the nickname of “One-Take Charlie” in Hollywood. While in Hollywood, Sinatra, with his abrasive persona, was either loved or hated by his fellow actors. One major actor by the name of Marlon Brando wasn’t a fan of Sinatra’s.

Guys and Dolls - 1955. Marlon Brando, Frank Sinatra
Guys and Dolls – 1955. Marlon Brando, Frank Sinatra. Photo By MGM/Samuel Goldwyn/Kobal/Shutterstock

And apparently, the feeling was mutual. Brando apparently didn’t agree with those who said Sinatra is one of the most likable stars in Hollywood. The two didn’t hit it off when they co-starred in 1955’s ‘Guys and Dolls.’ Sinatra allegedly wanted Brando’s role in the movie, and referred to his co-star as “Mr. Mumbles.” Brando, on the other hand, nicknamed Sinatra “Mr. Baldy.”

His Comeback to Movies

For a while, Sinatra was in Las Vegas and off the Hollywood radar. But Sinatra was desperate to find a role that would bring him back into the spotlight. In 1953, Columbia Pictures boss Harry Cohn was getting flooded with requests from people across Hollywood to give Frank Sinatra a chance to star as “Maggio” in Fred Zinnemann’s ‘From Here to Eternity.’

Montgomery Clift, Frank Sinatra
From Here to Eternity – 1953. Montgomery Clift, Frank Sinatra. Photo By Snap Stills/Shutterstock

Sinatra got the role, and during production, became a close friend with Montgomery Clift (an Oscar nominee actor). Sinatra later claimed that he “learned more about acting from him than anybody I ever knew before.” After years of critical and commercial decline, Sinatra finally got an Academy Award for Best Supporting Actor for his role in the movie. The win helped his career, to say the least, and put him back on the list of top recording artists in the world.

Sinatra Had Two Hits Called “New York, New York”

Did you know that Frank Sinatra actually had two hits called “New York, New York”? The first single came out in 1949, from the movie ‘On the Town,’ and was written by Leonard Bernstein, Adolph Green, and Betty Comden. Then, 30 years later, Sinatra cut the theme from “New York, New York” by John Kander and Fred Ebb.

Frank Sinatra at The Albert Hall, London, Britain - Sep 1980
Photo By Andre Csillag/Shutterstock

Originally from Martin Scorsese’s 1977 movie, ‘New York, New York,’ Sinatra turned the tune into his signature song and even his onstage closer. Lyricist, Ebb, was pretty angry when Sinatra customized the lyrics to the song, adding the climactic phrase “A number one.” Then in 1993, Sinatra recorded the song yet again, but this time it was as a duet with Tony Bennett.

He Hated Some of His Songs

Barbara Sinatra, who died in 2017, claimed that “My Way,” one of Frank’s most beloved songs, did absolutely nothing for the singer. But that was a nice way of putting it compared to “Strangers in the Night,” which Frank bluntly called “a piece of sh*t” and “the worst f**king song I’ve ever heard.”

Frank Sinatra at the Long Beach Arena, California, America - 1994
Frank Sinatra at the Long Beach Arena, California, America – 1994. Source: Shutterstock

Speaking of bad songs, several people have died after performing the song “My Way.” Yes, it sounds strange and it really is. But ever since 2000, at least six people have died after, or even while performing Sinatra’s classic hit. Dubbed the “My Way Killings,” this strange phenomenon got so bad that there were some bar owners who removed the song from their playlist entirely.

He Had His Own Pasta Sauces

Did you know that Sinatra had his own line of pasta sauces? 1990 was a year in the post-Paul Newman, pre-Marky Ramone era in celebrity spaghetti sauce. And Frank sure filled the void. Despite being inspired by his mother’s own recipe, which I’m sure was tasty when she made it, the sauce was a flop. But you can find Mama Sinatra’s recipe online.

Frank Sinatra Pasta Sauce 3 Flavors

If we’re on the topic of strange but true Frank Sinatra food facts, then maybe you’’ appreciate this one. Sinatra reportedly took some tootsie rolls to the grave. According to the celebrity expert Alan Petrucelli, Frank was buried with some Tootsie Rolls. And not just that; he also had other stuff that he loved buried with him, like cigarettes, a lighter, and a bottle of Jack Daniels.

He Was the First John Mcclane

If you think some action-loving Hollywood scriptwriter came up with the idea for Die Hard, you can think again. The movie was actually based on Roderick Thorp’s crime novel, “Nothing Lasts Forever,” from 1979, which was a sequel to his 1966 novel, “The Detective.” And since Sinatra starred in the film adaptation of ‘The Detective,’ he was offered the role in its sequel. But at the age of 73, he correctly turned it down.

The Detective - Movie
Source: Amazon

Another random fact: Sinatra was an honorary tribal chief. He was titled the “Order of the Leopard,” which is the highest honor in Bophuthatswana (a quasi-nation state in South Africa). The honor was a given as a token of appreciation by President Lucas Mangope for Sinatra’s performances at the defamed (and later boycotted) Sun City casino.

His Last Tune

The last song Frank Sinatra ever performed on stage was “The Best is Yet to Come.” On February 25, 1995, he sang the tune for an audience of 1200 people on the last night of a golf tournament that had been named for him. Those words, “The Best is Yet to Come,” are written on his tombstone. Sinatra died with his wife at his side on May 14, 1998, after a heart attack.

The Ultimate Event' Concert at the Royal Albert Hall Liza Minelli Frank Sinatra & Sammy Davies Jr
The Ultimate Event’ Concert at the Royal Albert Hall Liza Minelli Frank Sinatra & Sammy Davies Jr. Photo By Alan Davidson/Shutterstock

He was 82 years old, and for the last few years of his life, he was in ill health and frequently hospitalized for heart and breathing problems, high blood pressure, pneumonia, and bladder cancer. He was also diagnosed as having dementia. The funeral was held at the Roman Catholic Church of the Good Shepherd in Beverly Hills, with 400 mourners in the Church and thousands of fans outside.