Frank Sinatra’s Life: How Ol’ Blue Eyes Sang His Way To Stardom

Frank Sinatra is undeniably one of the most influential music artists of the 20th Century. His career spans over 70 years, over the course of which he has sold 150 million records and proven himself to be a timeless American icon. But how exactly did Ol’ Blue Eyes rise to his phenomenal success? Read on to see his meteoric rise to becoming an icon and how his brushes with the law — which sparked his infamous mugshot — never seemed to get in the way.

The Origins Of The Voice

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On December 12, 1915, Frank Sinatra was the only son born to Italian immigrants, Marty and Dolly. Sinatra’s birth was no easy feat and he was pulled out with the aid of forceps, the force of which caused severe scarring to his left cheek, neck, and ear.

The process also perforated his eardrum, which caused permanent damage. Sinatra weighed a whopping 13.5 pounds at birth, so it’s no wonder getting him out was such an ordeal. They placed him on the kitchen counter initially thinking he was dead until his grandmother ran him under some cold water.

Frank Sinatra Was Called “Scarface”

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Because of the damage caused at his birth, Sinatra underwent a childhood operation on his mastoid bone, which caused more scarring on his neck. Growing up, kids made fun of him by calling him “Scarface” and it upset him so much that he hated the doctor who delivered him. To make matters worse, he suffered cystic acne in adolescence which caused pitting in his cheeks.

Despite the confidence he exuded throughout his career, he might have been a bit self-conscious about his scars, which he would try to cover with makeup as an adult. As a result, he infamously hated being photographed from his left side.

Frankie Began Singing At An Early Age

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Sinatra’s parents owned and operated a tavern named Marty O’Brien’s during the 1920s. Despite the Prohibition, local officials refused to enforce the law and it was rumored that the Sinatra’s sourced their alcohol from the Mafia. Sinatra did his homework at the tavern and sometimes sang over the player piano for spare change.

Taking an interest in singing early in life, Sinatra allegedly would sing on street corners for pocket money. His mother Dolly was not fond of the idea of Frank becoming a singer, but she couldn’t deny that her son had talent, which she noticed when Frank was at least 11 years old.

Dolly probably never imagined her son would end up in jail, but one day he did — and you’ll never guess what for!

His Musical Pursuits Outweighed His Education

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Sinatra took his passion for singing more seriously than he did his studies. After finishing middle school, he attended A.J. Demarest High School where he would arrange bands for school dances. However, he was only enrolled in high school for a mere 47 days before getting himself expelled for “general rowdiness,” with the principal and his teachers noticing his lack of enthusiasm for learning.

With his parents’ disappointment, Sinatra’s father insisted that he find a job to avoid becoming a bum dropout. In addition to taking odd jobs from family connections, Sinatra would sing at other local bars and take elocution lessons from vocal coach John Quinlan.

Frank Sinatra’s First Big Break With Tommy Dorsey

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In 1935, Sinatra joined the 3 Flashes, a local Italian-American singing group who admitted they at first let him join since he had a car. By 1938, he became a singing waiter at a New Jersey roadhouse that was connected to WNEW radio station, where he performed live and started sharing his vocal talent with the world.

The following year, he joined the Chicago-based Tommy Dorsey band as a lead singer, earning $125 a week at the Palmer House. Tommy Dorsey became something of a father figure to Sinatra and he was so amazed by the kid’s talent, that he would almost forget to perform his own solos during shows.

Frank Sinatra Was Convicted On “Seduction” Charges

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You may have seen Frank Sinatra’s mugshot at one point, but the reason it exists is even more scandalous. In 1938, 23-year-old Sinatra was in a relationship with Nancy Barbato but while working at the roadhouse, he had an affair with another woman who tried to attack Nancy after she found out about her. Sinatra told the other woman to back off, but not before she went to the police, who initially arrested Sinatra on charges of seduction.

As it turned out, the other woman was married so the charges were changed to adultery. At the end of it all, Sinatra only spent half a day in jail and was released on a $500 bond.

This, of course, was nothing compared to the very public scandal Sinatra would find himself in many years later.

Sinatra Had A Family Before He Hit It Big

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In 1939, Sinatra married Nancy Barbato and their first child, Nancy Sinatra, was born the following year. In 1944, their son, Frank Sinatra Jr., was born. The family resided in their home state of New Jersey for their children’s early years until moving to Hollywood in order for Frank Sr. to pursue his budding career as a singer and actor.

After settling in California, the Sinatras welcomed their third and final child, Tina, in 1948. However, Sinatra’s rising popularity and rubbing elbows with Hollywood’s finest would lead to his first marriage’s demise, as you’ll soon learn.

Frank Sinatra Knew He Was Good On His Own

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Frank Sinatra recorded over 40 songs in his first year with Tommy Dorsey, which often became chart-topping hits. Due to Sinatra’s success, Dorsey reluctantly allowed him to record some solo songs in 1942, including “Night and Day” and “This Song is You.” Upon hearing his recordings, Sinatra reached a turning point in his career and realized he needed to go solo.

This led to a legal battle with Dorsey, who was contracted to 43% of Sinatra’s lifetime earnings. Things were settled by 1943 and although Sinatra’s relationship with Dorsey ended bitterly, Sinatra was already a rising solo star and burgeoning teen idol.

His Early Fans Were Paid To Scream, But The Hype Was Very Real

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Frank Sinatra debuted as a solo singer on December 30, 1942, at the Paramount Theatre in New York performing for four weeks after the Benny Goodman orchestra. This was the start of what was called “Sinatramania” as his appeal to teenaged “bobby soxers” revealed a whole new market for pop music. His fans called themselves “Sinatratics” and almost 1,000 fan clubs dedicated to him were reported in America.

Publicist George Evans reportedly had girls audition to be front row at Sinatra’s shows by seeing who could scream the loudest, paying them five bucks to help incite excitement among the audience.

The Bobbysoxers Of The Sinatra Era

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Frank Sinatra’s fans were so obsessive, they’d pin his pictures to their clothes, bribe hotel maids to let them touch his bed, and when they had the chance to see him in person, they’d aggressively try to steal the clothes off his person. In October 1944, Sinatra returned to the Paramount Theatre where bobbysoxers lined up in droves and waited all night to see him perform.

His shows accommodated up to 3,500 fans, many of whom refused to leave at the end of a performance, causing the 35,000 fans left outside to grow so anguished and rowdy, it was dubbed the Columbus Day Riot.

How Frank Sinatra Avoided The WWII Draft

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Already famous by the time World War II came around, he notoriously avoided getting drafted when he was classified 4F, meaning he was unfit for military service. Newspaper columnist Walter Winchell alleged that Sinatra managed to bribe his way out of the draft, paying $40,000 for the 4F classification but FBI probes sent to investigate this claim determined that it was false.

Sinatra’s permanently punctured eardrum was a major factor, as well as his claims of anxiety in crowds and commotion. Considering his celebrity, doctor’s didn’t question this and downplayed emotional instability as another factor. Sinatra was never able to live this down.

This and another scandal to come by the end of the ’40s would ultimately lead to the first demise in Sinatra’s career.

Breaking Into Hollywood Films

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As his singing career took off in the early ’40s Sinatra also ventured into film, making his debut in 1943’s Reveille with Beverly, with a cameo appearance as himself singing “Night and Day.” Sinatra starred alongside Gene Kelly in 1945’s Anchors Aweigh, which became a major success and was nominated for several Academy Awards.

Sinatra sang “I Fall In Love Too Easily” for the film, which was also up for Best Song. That same year, Sinatra was awarded an honorary Oscar for his role in the short film The House I Live In, which promoted racial and religious tolerance.

He Strayed Away From His First Wife… Many Times

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In Hollywood, Sinatra entered into a string of extra-marital affairs, most notably with Ava Garnder, which became public much to Nancy Sr.’s embarrassment. In 1950, Frank and Nancy legally separated, which allowed for Frank and Ava’s relationship to become more serious. After Frank and Nancy officially divorced in 1951, he married Ava Gardner later that same year.

A devout Catholic, Nancy Sr. never remarried. Though his affair with Gardner is just one of many personal transgressions throughout Sinatra’s life, by many accounts he was reported to remain a devoted father to his two daughters and son despite it all.

This was the beginning of a dim era in Sinatra’s career, which was marked by some drastic moments, as you’ll soon learn.

After Frank’s Marriage To Ava Gardner

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By the time Sinatra married Ava Gardner, his career was already in steady decline as his record releases failed to match the success of his first album, The Voice of Frank Sinatra in 1946. That, in addition to his extra-marital affairs and having not joined the troops during World War II, caused Sinatra’s popularity to wane.

Eventually, he was dropped by his label at the time – Columbia – and also lost his contracts with Hollywood studios. Sinatra was then forced to turn to Las Vegas, performing at hotels where it was clear his celebrity had begun to fade, as only a handful of people showed up to his shows.

The Hype Died Down Quickly

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In 1951, Sinatra began performing shows at the Desert Inn in Las Vegas and the Riverside Hotel in Reno, Nevada. By 1953, he began performing three times a year at the Sands Hotel and Casino, pioneering the trend of Las Vegas’s residency entertainers. But still, while his performances at the start of his career were filled to capacity, his shows in Vegas and other places were unable to compare.

Sinatra’s Vegas performances were reportedly half-filled by wildcatters and ranchers, while a performance at a 1,200-seat venue in Chicago was only filled with 150 people. In 1952, he had succumbed to performing at county fairs.

Sinatra Felt Hopeless

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Frank Sinatra fell into a deep depression during the early ’50s and attempted suicide on multiple occasions. Once while walking through Time Square, Sinatra saw a crowd of girls excitedly waiting for an Eddie Fisher concert. Sinatra felt so washed up that he returned to his apartment, put his head over the stove top, and turned on the gas before he was found in time by his manager.

His relationship with Ava Gardner had also grown so tumultuous, that at one point he walked into their room with a gun pointed at his head. A shot was fired as Gardner tried to wrangle the weapon away, though no one was hurt.

This was one of the lowest points for Sinatra, but he would soon pick himself up and be at the top of his game with a special group of friends.

His Amazing Career Comeback Includes An Oscar Win

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Frank Sinatra’s slump only lasted a few years before his career took a turn for the better in 1953 when he co-starred in the film From Here to Eternity and signed a seven-year contract with Capitol Records. In 1954, the film won eight of its 13 nominations, one of which was awarded to Sinatra for Best Supporting Actor in his role as Italian-American Private Angelo Maggio.

That same year, he released his first two records with Capitol — Songs for Young Lovers and Swing Easy! — the latter of which was named Album of the Year by Billboard. It was clear that Sinatra had made a remarkable comeback.

Sinatra Regularly Rubbed Elbows With Hollywood’s Finest

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While Sinatra steadily continued to reboot his career through the rest of the ’50s, he also made a particular group of friends during this time. It all started when Sinatra, just after having moved to Hollywood, began hanging out with Humphrey Bogart and the rest of his drinking buddies. Bogart often invited his Hollywood friends over to his home in Holmby Hills. That included the likes of Errol Flynn, Tony Curtis, Judy Garland, Dit Luft, Nat King Cole, and others. It was reported that when Bogart’s wife Lauren Bacall saw the group together after a night in Vegas, she said, “You look like a [expletive] rat pack.”

The Rat Pack Didn’t Actually Call Themselves That

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Sinatra liked having the company around and after Bogart’s death in 1957, he formed a group of his own. Sinatra was acquainted with Sammy Davis Jr., Dean Martin, Peter Lawford, and Joey Bishop having worked with them in show business and eventually, the group grew close. After Sinatra performed with Martin at the Sands in 1959, they set the precedent for performing together as the Rat Pack. They became known for their banter, drinking, and cool attitude with Sinatra as their unofficial leader. However, they preferred to be called “the Summit” or “the Clan” rather than the Rat Pack, which is what the public knew them as throughout the ’60s.

Frank Drinks A Gentleman’s Drink

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By the Rat Pack days, Frank Sinatra was at the height of his celebrity with a reputation for a boozy ladies man and host. If you ever wondered what his go-to drink of choice was, Sinatra was a man of class and therefore wouldn’t overcomplicate things.

Sinatra’s signature drink was two fingers of Jack Daniel’s whiskey with precisely four ice cubes and a splash of water. Calling it “a gentleman’s drink,” Sinatra liked to cup the drink, insulated by a cocktail napkin, being careful to never touch the rim.

With Sinatra’s career back on track, it wasn’t long before drama re-entered his life and affected his family.

Sinatra Starts His Own Record Label

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By the ’60s, Sinatra grew restless in his contract with Capitol Records which led to a years-long feud with producer Alan Livingston, who had signed the artist at his all-time career low. Eventually, Sinatra decided to form his own label, Reprise Records, which promised artists creative control and “complete ownership of their work, including publishing rights.”

To give the record label some credit and prove he was taking his music in a new direction, Sinatra began working with new producers such as Neil Hefti, Don Costa, and Quincy Jones. Sinatra’s first album with Reprise was 1961’s Ring-a-Ding-Ding!, which peaked at four on the Billboard charts.

Sinatra’s Label Supported The Artists

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Sinatra, of course, signed fellow Rat Pack members Dean Martin and Sammy Davis Jr. in the record label’s early years. Also included in the original roster were Bing Crosby, Redd Foxx, Jo Stafford, and Sinatra’s daughter Nancy. Because the acts signed to Reprise Records were all different genres, the Reprise LP logo was designed with several different versions.

A steamship represents pop records, for example, while an owl represented spoken word and comedy. For Sinatra’s own records, he simply used a picture of himself. Eventually, Sinatra would sell Reprise Records for a reported $80 million.

Frank Sinatra Jr. Gets Kidnapped

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With his career back on track, Frank Sinatra’s personal life was still not without drama. By this time, Sinatra’s son, Frank Jr., was following in his father’s footsteps and trying to make it on his own as a singer. After a performance at Harrah’s in Lake Tahoe on December 8, 1963, the unsuspecting Frank Jr. was kidnapped from his dressing room.

Authorities were immediately alerted and police roadblocks were set-up around the area, but the kidnappers managed to bluff their way out of Lake Tahoe and back to Southern California. The elder Sinatra worked closely with the FBI, who told him to wait for the kidnappers’ demands before taking action.

Though Sinatra enlisted the help of the FBI, you may be surprised at who else offered their assistance.

Sinatra Always Carried Dimes

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It was at this time Sinatra Sr. began the lifelong habit of carrying a roll of dimes in his pocket since he could only contact the kidnappers by payphone. The suspected kidnappers were 23-year-old Barry Keenan and Joe Amsler, who’d been following Sinatra Jr. for some time before making their move.

They employed a third conspirator, John Irwin, as the point of contact for Sinatra Sr., who was told to wait for the ransom instructions. Finally, on December 10th, Irwin passed along the demand for $240,000. The drop point was in between two school buses in the Sepulveda neighborhood of Los Angeles.

The Kidnapping Could Have Ended Way Worse

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After the money was collected, Irwin released Frank Jr. unharmed on Mulholland Drive in the Hollywood Hills. Frank Jr. was picked up by police and brought to his mother’s home in their trunk to avoid a public scene. Irwin confessed to his brother, who alerted the FBI in San Diego.

Since the FBI worked with Sinatra Sr. to track the ransom money, Keenan and Amsler were captured and arrested just hours later. There was an argument that the ordeal was a publicity stunt on behalf of Frank Jr., but this claim was debunked with a confession letter penned by Keenan. All three perpetrators were later convicted.

Questionable Sources Reached Out To Sinatra

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Frank Sinatra was wise to cooperate with the FBI on his son’s kidnapping, as he had offers of assistance from then-Attorney General Robert Kennedy and mob boss Sam Giancana. Taking help from Giancana might not have been the best choice, considering that Sinatra has long been suspected of having ties to the mafia.

These ties date back to his upbringing in Hoboken, New Jersey, where his parents allegedly used mafia assistance to stock their tavern with bootleg booze and his maternal uncles have had brushes with the law for their explicit involvement.

Despite his alleged connections with the mafia, Sinatra was soon rubbing elbows with some pretty significant political figures.

People Believed He was in with the Mafia

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Sinatra has been rumored to use mafia connections throughout his career. In order to get out of his contract with Tommy Dorsey, it was rumored that Sinatra’s mobster godfather Willie Moretti coerced Dorsey by holding a gun to his head. There was also a rumor that Sinatra only got his part in From Here to Eternity because someone planted a severed horse’s head in the director’s bed.

These claims were proven false, yet suspicions still arose when Sinatra was blatantly pictured with mafia bosses on a trip to Cuba. Sinatra has never admitted to direct involvement with organized crime, but with his New Jersey origins and his Italian-American heritage, it hasn’t stopped speculation.

The FBI had an Extensive File on Sinatra

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Frank Sinatra actually had an extensive file with the FBI. The file began after there was speculation that Sinatra avoided the draft with bribery, which was proven false. Sinatra also was flagged as a Communist sympathizer in the ’50s for his role in the short film The House I Live In from 1945.

President Hoover had started Sinatra’s file after a radio listener wrote to the FBI saying, “The other day I turned on a Frank Sinatra program and I thought how easy it would be for certain-minded manufacturers to create another Hitler here in America through the influence of mass hysteria.”

He Wanted To Be JFK’s Best Friend

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Given his clout at the time, Sinatra helped campaign and fundraise for the Democratic party during the ’60s. He became fast friends with then-candidate John F. Kennedy and the pair reportedly bonded over their pursuit of women. However, Sinatra’s alleged ties to organized crime caused their relationship to fizzle as JFK entered the presidency.

In 1962, when Sinatra was asked to host JFK at his Palm Springs estate, he prepared by building a helipad on his property out of his own pocket. But when JFK ended up staying with Bing Crosby, Sinatra was so upset he destroyed the new helipad with a sledgehammer.

Sinatra’s temperament may come as a surprise, but even more surprising are his real thoughts on one of his most popular songs…

Frank Sinatra’s Other Women

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Even before his marriage to Ava Gardner, Sinatra was known to be romantically involved with other Hollywood starlets, including Lana Turner, Judy Garland, Juliet Prowse, and Lauren Bacall, to name a few.

After his second marriage dissolved, Sinatra was romantically linked to Marilyn Monroe, who reportedly wanted to marry him, though not even a ladies’ man like Sinatra could handle the blonde bombshell for all that she was. By the time Sinatra’s career was back in full swing in the ’60s, he had married for a third time in 1966 to actress Mia Farrow.

Frank Marries Barely-Legal Mia Farrow

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Frank Sinatra’s relationship with Mia Farrow raised many eyebrows since at the time, Sinatra was 50 years old and Farrow was just 21. When she was still a teen, Farrow wandered from the set of Peyton Place to watch Sinatra film Von Ryan’s Express.

Sinatra married Farrow under the pretense that she would quit acting, which she agreed to do at the time. But after Farrow landed the lead role in Rosemary’s Baby, Sinatra served her divorce papers when filming went on for too long. Their marriage only lasted two years, but they reportedly remained close until his death.

What Frank Sinatra Really Thinks Of “My Way”

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In 1968, Sinatra recorded “My Way,” which Paul Anka adapted from the French song “Comme d’habitude” by Claude François. “My Way” became the best-known Sinatra song on the Reprise label, if not Sinatra’s best-known song ever. However, Sinatra reportedly grew to hate the song.

Reports say that Sinatra told songwriter Evan Drake in later years that he “hated boastfulness in others” and that he viewed “My Way” as a “self-aggrandizing tribute” to himself. Though Sinatra wasn’t a fan of it, “My Way” became a successful hit and has been recorded by more than 60 artists.

It was while performing “My Way” that Sinatra had an on-stage scare in 1994.

Frank Sinatra’s “Retirement”

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After the lukewarm reception to his 1970 album Watertown and having left his residency at Caesars Palace, Sinatra announced his retirement at age 56. In a 1971 interview with LIFE, Sinatra said, “I’ve had enough. Maybe the public’s had enough, too. I’ve got things to do. Like the first thing is not to do anything at all for eight months, maybe a year.”

He continued, “Physically, the voice is a long way from going. Hell, I just quit, that’s all. I don’t want to put any more makeup on. I don’t want to perform anymore. I’m not going to stop living. Maybe I’m going to start living.”

Sinatra Topped Off His Career With A Comeback Tour

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Sinatra’s self-imposed retirement didn’t actually last very long. In 1973, Sinatra released Ol’ Blue Eyes Is Back which ranked number 13 on Billboard. That year a television special, Magnavox Presents Frank Sinatra, reunited Sinatra with Gene Kelly.

Sinatra also returned to Vegas and embarked on a worldwide comeback tour, where he came under fire in Australia for referring to the press as “bums, parasites,” and other expletives after journalists were aggressively following Sinatra’s every move. Instead of apologizing to the country during a televised concert, Sinatra said, “I love your attitude, I love your booze.”

Sinatra’s Fourth And Final Wife Is The Least Memorable

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In 1976, Sinatra married his fourth and final wife, Barbara Marx, who was formerly married to actor Zeppo Marx. While Barbara has survived as Sinatra’s longest-serving wife, she is relatively unknown and unpopular compared to his former wives. Some reports say that Barbara was in an endless pursuit to get Sinatra to marry her, even going so far as to convert to Catholicism.

Barbara’s relationship with Sinatra’s three children was notoriously stormy, if not nonexistent. Despite this, Sinatra remained married to Barbara until his death and much of the information about him can be found in Barbara’s memoir, Lady Blue Eyes.

Sinatra Initially Didn’t Want To Sing “New York, New York”

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In 1980, Frank Sinatra released Trilogy: Past Present Future, for which he rerecorded “Theme from New York, New York,” from the 1977 film by Martin Scorsese. The hit was written for and performed by Liza Minelli in the film, but Sinatra’s version quickly became one of his signature songs.

In an interview with Telegraph, Barbara Marx said that she was the one who convinced Sinatra to include the song in his shows: “[He] said, ‘No, that’s Liza’s song, and I’m not going to do it.’ So I waited a while and brought it up again and finally, he sang it and it just took off.”

In His Old Age, Sinatra Had Loyal Fans

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Frank Sinatra continued to make music and perform through the late ’70s and the ’80s, despite getting older. In 1982, Sinatra signed a three-year contract worth $16 million with Golden Nugget in Las Vegas where many have noted that by then Sinatra’s voice had grown dark and coarse.

Though Sinatra’s voice wasn’t what it used to be, people still came to see Ol’ Blue Eyes perform and were in awe of his presence. By this time, Sinatra performed often for charities and donated much of his earnings to different causes.

Sinatra’s Best-Selling Album Was Controversial

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In 1993, Sinatra released Duets with Capitol Records. Duets became his best-selling album and it reached number two on Billboard upon its release, becoming the only Sinatra album to ever achieve a triple platinum certification. Duets featured Sinatra’s greatest hits with accompaniment from younger singers of various genres. As successful as Duets was, it was hotly criticized for the fact that Sinatra never actually joined the younger artists in the studio. Sinatra didn’t actually rerecord his songs, probably because his voice was different by the ’90s, and the guest singers were instructed to sing on top of his vocals in a complementary way.

Sinatra Collapses At One Of His Final Concerts

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At a concert in Richmond, Virginia in 1994, Sinatra fainted and collapsed on stage while performing “My Way.” During the last chorus of the song, onlookers told The New York Times, “In a real clear voice, he said, ‘Get me a chair,’ then he fell to the floor. When they brought a wheelchair, everybody clapped, because they didn’t seem to need a stretcher.”

At this point, Sinatra was already 78 years old and though he was still performing live, there have been reports that his memory would begin to fail him while on stage and he wouldn’t be able to remember the words to some of his songs.

Frank Sinatra Almost Made It Out Of His Century

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In his later years throughout the ’90s, Sinatra’s health was failing him as he was frequently hospitalized for heart and breathing problems, as well as high blood pressure, pneumonia, and bladder cancer. In 1998, Frank Sinatra passed away in Los Angeles at the age of 82 after a heart attack.

He was buried in a blue business suit with mementos that family members put into his casket, including cherry Life Savers, Tootsie Rolls, a bottle of Jack Daniel’s, a pack of Camel cigarettes, a Zippo lighter, and a roll of dimes. “The Best Is Yet to Come” is engraved on his tombstone and it was the last song Sinatra performed in public in 1995.