Across all of entertainment history, few performers have secured the legendary status of Frank Sinatra. When a celebrity counts among their nicknames the likes of ‘The Sultan of Swoon’, ‘The Chairman of the Board’ and even just ‘The Voice’, it’s difficult to overstate their contributions to the world of music and film. With his signature sharp suit and trilby hat, Frank Sinatra created an image of charm and glamour that we now see as indicative of the era as a whole.

However, Sinatra is a far more complicated and interesting figure than just the man at the head of the Rat Pack. From his alleged involvements with the Mob to his numerous salacious affairs, Sinatra’s life itself often played out like a 50s gangster movie. That drama was also balanced by a profound sense of kindness, as seen in how he treated his collaborators, friends and even the President of the United States. Today, we’re digging into the complicated history and legacy of this award-winning musician and actor – looking at the secrets, the scandals and the songs.

1. Born blue

Frank Sinatra had a troubled life from the start, and by the start, we mean the very beginning. When Sinatra was born, he was blue and not breathing, and the birth had been so troubling that the doctors in the room just assumed that he wouldn’t make it.

Given how difficult the birth had been for his mother Dolly Sinatra, the doctors opted to keep the focus on her to ensure that she pulled through this difficult ordeal. As a result of this, in his first moments, Frank Sinatra was given very little medical attention, as the doctors were more focused on keeping his mother alive.

2. Grandma to the rescue

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Given that the doctors in the room when Frank Sinatra was born were both convinced that he wouldn’t make it and knew that his mother’s care was of higher priority, there is a high chance that one of the greatest singers the world has ever known might have died as a baby.

Thankfully for him, and for the world at large, the doctors weren’t the only ones in the delivery room that day. Frank’s grandma was also present, and it was she who took the blue baby and ran his face under a cold tap, which shocked him enough to take his first breaths and convince the doctors to pay attention. Good old grandma.

3. Scarred for life

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Sinatra might have survived his rough entry into the world, but he didn’t make it out entirely unscathed. The difficult delivery left Sinatra with a burst eardrum in one ear, a difficult malady for a future career musician and singer to have to deal with.

The delivery also left him with scarring on his left cheek, neck and ear, which remained with him for the rest of his life. These scars are often painted out of photographs of him from the early years, but are faintly visible in much of his film and TV work, beneath the make-up.

4. Terrible teens

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The scarring that Frank Sinatra received during birth was unfortunately not the end of his cosmetic troubles. As a young pre-teen, Sinatra had to undergo a surgical operation on his mastoid bone, which left a mass of scarring on his neck even after he had fully healed from the operation.

As if that wasn’t bad enough, Sinatra also developed cystic acne in his teen years, which left him with further scarring on his face and neck, as well as an uneven skin texture that remained with him throughout his life. However, none of those things would stop him from having immense success with the ladies later in life…

5. Cruel schoolmates

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Despite the extraordinary person that Frank Sinatra would grow into in later life, he was not immune from one of the saddest banalities of most people’s school years: bullying. Sinatra was not ignorant of the teasing that went on at his school, as his classmates would often call him Scarface and mock his appearance.

Sinatra was famously raised Roman Catholic but was a staunch critic of organised religion throughout his life. There’s no knowing if his doubt began in his school years when his religious upbringing did nothing to stop his fellow classmates from picking on his physical insecurities.

6. Boxing clever

Frank’s father was called Antonio Martino Sinatra, but he spent much of his life going by Marty O’Brien. O’Brien was predominantly known as a boxer who fought matches in the bantamweight class, which focused on opponents between 115lbs and 118lbs.

O’Brien also spent almost a quarter of a decade working as a firefighter in the Hoboken Fire Department, and in that time he managed to work his way up to the rank of captain. O’Brien managed to accomplish this while also being almost illiterate, which only increased Frank’s esteem for him.

7. Deliver us from evil

Frank Sinatra’s mother, Dolly Sinatra, was just as much a singular individual as her husband. Dolly worked predominantly as a midwife, earning $500 for each delivery she successfully completed. However, she also had a gift for languages, and also worked as a translator in the multicultural area where Frank grew up.

Throughout their local area, Dolly was known as a strong and forceful personality with a nurturing streak and an affinity for justice. Her legacy is a complicated one, though, owing to the numerous causes she committed herself to over the years.

8. A business on the side

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Throughout Dolly Sinatra’s life, she was plagued by rumours about a secondary business that she ran in addition to utilising her skills as a midwife. Many said that she also ran an underground abortion clinic, secretly offering help to women and girls who had found themselves in trouble.

Dolly Sinatra’s secondary, more secret business predominantly offered help to the local population of Italian Catholic schoolgirls. This business earned her the nickname Hatpin Dolly, both from her detractors and those who were grateful for the services that she offered.

9. Standing up for your beliefs

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Dolly Sinatra’s secret career as Hatpin Dolly was not the only way in which her commitment to her beliefs came through. A fervent Democrat, she often campaigned for progressive causes that she believed in, especially the women’s suffrage movement when it came to America.

Dolly Sinatra was well known amongst the Democrats of her area, and she once even volunteered to chain herself to a building to fight for women to get the vote. These actions did cause her to be much admired in those particular political circles, even if she was derided outside of them.

10. A mother’s secret

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For the most part, stories of Dolly Sinatra’s life paint a flattering picture. They show her to be a hard worker, and a woman who was committed to her principals with an altruistic streak.

With that said, not everything about Dolly Sinatra was idyllic. At least according to Frank Sinatra’s fourth wife Barbara, Dolly Sinatra also physically abused Frank Sinatra while he was growing up, with Barbara alleging that Dolly definitely “knocked [Frank] about a bit”.

11. Performing for pennies

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Frank Sinatra’s love of music started early, with his first gigs consisting of him sitting atop the piano at his family’s tavern, singing along to the pianist’s accompaniment. Kind patrons would often tip him pennies as they listened to him sing, meaning the first money Sinatra ever made was through performing.

However, many have speculated that this establishment was an illegal, Prohibition-era speakeasy, and so business couldn’t exactly be above board. If that was the case, then Sinatra’s first pennies were indeed made through performing, but they were also made illegally.

12. Best dressed

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Like many working-class families of the time, Frank Sinatra’s parents struggled to get by during the Depression. However, they did have enough excess money for the occasional vice, and Dolly Sinatra had very particular views about what that money should be spent on.

With any money the family had to spare, Dolly would pay for high-quality clothes for her son, leading to Frank becoming known as “the best-dressed kid in the neighbourhood”. Given that Sinatra later became known in part for his sharp suits and trilby hats, the fact that he set himself apart early using fashion seems appropriate.

13. Prom performances

When Frank progressed to high school, he was already more interested in music than he was in his lessons. He spent most of his time organising bands to play at the school’s various functions, such as prom, and begged the teachers to be allowed to perform with them.

However, for as much as his fellow students were unkind to Frank, his teachers were doubly so. One teacher even famously told him that he had “no real talent for anything”, especially not music. Undeterred, Sinatra continued to be an integral part of his school’s music program.

14. General rowdiness

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Frank Sinatra had a lot of factors working against him at school. He was insecure about his facial scars and acne, he was bullied by his fellow students, and his teachers were both derisive and dismissive towards him. With all of these problems, it’s a wonder that Sinatra found the guts to walk in each day and pick up a pen.

The constant chorus of doubts voiced against Sinatra every day did have an effect on his schooling. Sinatra found it hard to concentrate, and developed a reputation for being loud and disruptive. He was expelled from high school after just 47 days, with his teachers citing “general rowdiness” as the reason.

15. A Jersey delivery boy

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Sinatra’s expulsion from school angered both of his parents, who wanted him to get an education and make something of himself. To please his mother, Sinatra enrolled in business school, but he only lasted for 11 months before dropping out.

Instead, Frank moved to New Jersey and became a delivery boy for the Jersey Observer, alongside his godfather Frank Garrick. Following that, he worked at various shipyards around the coast, putting his small earnings towards his first professional vocal lessons.

16. Two girls are better than one

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Frank Sinatra’s early days in New Jersey as he struck out on his own were fraught with drama, and much of that drama was of his own making. Most of Sinatra’s early problems came down to the fact that he was allergic to monogamy, in one instance dating two women at once without telling either of them.

For a time, Frank was seeing both Toni Della Penta and Nancy Barbato, without either of them knowing of the other’s existence. With that said, it didn’t take either girl very long to figure out that they were being played, and Sinatra soon found out the consequences of messing the women in his life around.

17. A dangerous cat fight

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When the two women realised that they were being cheated on, Toni Della Penta went so far as to attack Nancy Barbato in the street. Unfortunately, Della Penta was pregnant at the time, and she suffered a miscarriage either due to the stress of the situation or the altercation itself.

After this incident, Della Penta remained both dedicated to Sinatra and absolutely furious with him, and she swore she would get revenge on both Frank and rival Barbato. Della Penta turned out to be true to her word, and the resulting drama was something right out of a soap opera.

18. Making a commitment

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Della Penta resolved to give Frank an ultimatum, and told him to choose between her and his other girlfriend, Nancy Barbato. Unfortunately for Della Penta, Sinatra told her that he was committed to making a life with Barbato, and couldn’t see Della Penta anymore.

Toni Della Penta was already furious at this news, but became even more incensed when Frank told her that Barbato was pregnant with his child. This announcement was actually a complete fabrication on Sinatra’s part, as Barbato was not pregnant at all, but the news did its job at driving Della Penta away.

19. Jail for seduction

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Unfortunately for Frank, this was not the end of the trouble. As a last resort, Toni Della Penta took the story of Sinatra’s cheating ways to the police, as in those days a man could be arrested for endangering the reputation of women in this way.

Sinatra went to jail on a morals charge of seduction, and Della Penta soon joined him behind bars. Instead of seduction, Della Penta was charged with assault, after she got into a gratuitous fight with Sinatra’s mother Dolly. Della Penta had gone to speak to Dolly in a rage, hoping Sinatra’s mother would take her side, but things didn’t exactly work out in her favour.

20. Not a happy marriage

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Once Frank got himself out of jail, he was true to his word and married Nancy Barbato on the spot. Their first child, Nancy Sinatra, was born later that year. It should have been a happy resolution to a tumultuous set of circumstances, but their marriage was just as chaotic as the situation it was born out of.

Throughout the 12-year-long marriage, Frank indulged in numerous extra-marital affairs, which were well publicised in the gossip magazines and barely hidden by the man himself. This led Sinatra and Barbato to fight constantly, a world away from the happy-go-lucky young couple they had been when Sinatra was working as a New Jersey lifeguard.

21. Designated driver

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When Sinatra wasn’t getting into salacious relationship drama, he was attempting to begin his career as a professional singer and performer. His first step on the ladder was befriending local group The Three Flashes in 1935, which he did by asking his mother to ask them to let him join.

The group obliged and found humour in the fact that the much younger man doted on the group so loyally. Fred Tamburro, the group’s baritone, even said later: “Frank hung around us like we were gods or something”. Most of the reason Sinatra was allowed to join the group had to do with the fact that he had a car and could drive, so he could ferry the other members of the group to and from gigs.

22. An important audition

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Frank soon grew tired of being a glorified chauffeur, however, and pressed the group to let him join in on their very next audition. The audition in question was for a musical slot on the Major Bowes Amateur Hour, a proto-singing competition which gave out prizes to those groups that won the hearts and votes of the audience.

The group successfully made it onto the show, and managed to win the competition handily. Renamed The Hoboken Four after the addition of Sinatra, they attracted 40,000 votes and won a six-month contract to perform on stage and on radio around the United States. Sinatra was promoted to lead singer, and became a huge hit with local audiences.

23. Band-hopping

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Ever-restless, it wasn’t long before Sinatra jumped ship from The Hoboken Four, this time opting to become the lead singer in the Tommy Dorsey band, replacing Jack Leonard. Before this, Sinatra had been performing with the Harry James band, but had grown frustrated with the lack of upward momentum and success.

For a while, Sinatra had been contented to stay, thanks to being encouraged to do so by his good friend Hank Sanicola, who also worked as the pianist for the group. However, Sinatra eventually insisted on being released from his contract, hoping that the Tommy Dorsey band would help him find the kind of fame he felt he deserved.

24. A musical father figure

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Frank Sinatra once famously said in an interview “The only two people I’ve ever been afraid of are my mother and Tommy Dorsey.” This was more appropriate of a thing to say than even Sinatra knew at the time, as he soon became a kind of surrogate son figure for infamous band leader Dorsey.

Dorsey had handpicked Sinatra to join his group, and made sure to take Sinatra under his wing personally as well. Sinatra sought to imitate a lot of Dorsey’s habits, even cultivating his own interest in toy trains because he knew that Dorsey admired them.

25. A family honour

Even when Sinatra was feuding with other members of the band, in particular, drummer Buddy Rich, the bond between Sinatra and Dorsey remained strong. In particular, each encouraged the other to become more and more of a demanding perfectionist, a trait which would become toxic later in their careers.

However, Sinatra still held Dorsey in the utmost esteem, and eventually bestowed on him the highest honour he could think of. In 1940, Sinatra asked Tommy Dorsey to become the godfather to first daughter Nancy, who was born in June of that year. Dorsey gladly accepted, bonding the two professionals together forever.

26. An unfair contract

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Despite the personal admiration Sinatra had for Tommy Dorsey, and the mounting success that they had found professionally together, all was not so idyllic behind the scenes. When Sinatra had band-hopped to join up with Dorsey, Dorsey had locked him in an ironclad contract, which entitled Dorsey to a portion of Sinatra’s lifetime earnings.

As well as entitling Dorsey to a stack of Sinatra’s money that he could have theoretically made without him, the contract was also incredibly difficult to be released from. Sinatra’s usual habit, of simply asking to be released from the contract and going on his way, was not going to work in this instance.

27. A broken friendship

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Eventually, Sinatra made the drastic decision to bank on the response he got from audiences whenever he went out on stage, and assume he could make it as a solo artist. Despite this seeming like a no-brainer now, it was an immense gamble at the time, as Sinatra risked losing his entire career.

After Sinatra had made the decision to go it alone, he was forced to sue Tommy Dorsey to get out of his contract. The legal battle was nasty and protracted, but Sinatra eventually won, and was granted the ability to begin recording solo music away from Dorsey’s group. In response, Dorsey bitterly remarked to Sinatra after the verdict: “I hope you fall on your ***”.

28. Getting the Mob involved

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Even if you only take the most mundane version of the story, the spat between Sinatra and Dorsey got pretty nasty. However, there are also those who believe that what really happened was even grimmer than the public version of events. Simply put: many have theorised that Sinatra got out of his contract by doing more than just pursuing legal action.

Sinatra’s professional break-up with Tommy Dorsey was the first time that rumours of connections to the Mob began to seriously plague him, and it wouldn’t be the last. Soon, newspapers were buzzing with the idea that Sinatra had sent a gangster to Dorsey’s house to threaten him, scaring him so much that Dorsey agreed to let Sinatra go for just a few thousand dollars. Yikes.

29. Professional fangirl

Throughout the 1940s, Frank Sinatra was the definition of a heartthrob. Mocked for his skinny frame and facial scarring as a youngster, now women flocked to Frank for his dazzling blue eyes and apparent sensitivity.

Women would scream themselves hoarse at Sinatra’s concerts, though that was at least partly because some were paid to do so. As unbelievable as it sounds, Sinatra’s manager and publicist George Evans held auditions to find the loudest cheering girls, and paid them to sit in Frank’s audiences and scream. It was an odd way of building hype, but it worked.

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30. A riot for seats

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In fact, George Evans may have made a mistake by playing up the already fervent Sinatra-fever. Soon Frank’s popularity grew to dangerous levels, with crowds of girls following him everywhere he went. In a kind of proto-Beatlemania, Frank Sinatra became an unparalleled star in the eyes of his young teen fanbase.

This incredible energy surrounding Sinatra came to a head when one of his shows sold out quickly, leading to a mass of 35,000 fans outside attempting to get into an already full venue. The authorities tried to turn the crowd away, but this only led to a riot as the mass of people attempted to catch a sight of Ol’ Blue Eyes.

31. Not fit for war

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Sinatra’s popularity was reaching new heights when world events threw a spanner in the works. Despite being a major celebrity, Sinatra was destined for the draft when it became evident that America would be joining World War II. However, when it came time for him to be medically assessed, Sinatra was categorised as 4-F, meaning “registrant not acceptable for military service”.

The official line was that Frank could not serve thanks to his perforated eardrum. However, many speculated that he had instead bribed a doctor with $40,000 to say that he could not fight in the war. The truth is somewhere between the two stories: Sinatra was denied the ability to fight thanks to his mental instability and depression, but that was not released publically so as not to destroy his career or reputation.

32. Going on tour

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The rumours about Sinatra paying a doctor to avoid the draft were so prevalent that eventually the FBI was forced to step in and investigate them. Thankfully, they quickly found that the story was without merit, clearing Frank to contribute to the war effort in his own way.

Towards the end of the war, Sinatra entertained the troops by participating in many OSO shows, usually with American comedian Phil Silvers. These tours were intended to boost morale by entertaining the soldiers overseas, and they were also broadcast domestically on the radio to boost morale at home as well.

33. A Christmas gift

Despite serving his country the best way he knew how, and managing to keep rumours of his Mob connections at bay, Sinatra’s personal life continued to dent his pristine public image. One Christmas, Sinatra’s wife Nancy went to fetch something from Sinatra’s car, and discovered a gorgeous diamond bracelet on the front seat.

Believing it to be a sloppily hidden Christmas present, Nancy didn’t say a word about it, and waited patiently to be presented with the gift come Christmas Day. Unfortunately for her, Nancy was about to live out a real-life version of Love, Actually, as the bracelet wasn’t actually meant for her.

34. The wrong recipient

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Nancy found out that the gift her husband had bought was not intended for her in the worst possible way. Every year, the Sinatras threw a grand Christmas party, with many celebrities and other influential figures in attendance. It was at this glamorous party that Nancy discovered the truth.

While attending to her hostess duties, Nancy noticed the actress and model Marilyn Maxwell talking in the corner of the room. On her wrist was the beautiful diamond bracelet that she had seen in her husband’s car earlier and assumed was intended for her. When no gift was forthcoming from her husband, and he continued to pay attention to Maxwell all evening, Nancy’s suspicions were confirmed.

35. A second affair

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When confronted by his wife, Frank was forthcoming about his flirtation with Maxwell. However, he opted to simply maintain that it had not meant anything. Nancy forgave him, but a second affair soon followed the first, and this one Nancy found far more difficult to forgive.

While Nancy was at home, pregnant with what was to have been their fourth child, Frank had struck up a friendship with Lana Turner, the pin-up model and film actress. That friendship clearly blossomed into something more, with the pair frequently making time to see each other. When Nancy found out, she was allegedly so furious that she terminated her pregnancy, unable to believe that Frank could be faithful to her.

36. Romantic getaway

The final straw in came in 1949, when the press reported on Frank being seen with Hollywood legend Judy Garland. The pair were on a romantic beachside holiday, but were discovered by journalists and photographers despite their attempts to be stealthy,

Garland had just suffered a mental breakdown due to her hectic schedule and had gone to meet with Frank after finishing up an extended hospital stay. The official line was that Sinatra, as someone who had worked with Garland in the past, was just there to comfort and support her during her recovery, but the rumours suggested otherwise.

37. An unceremonious end

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Nancy had always struggled along in her relationship to Frank despite his infidelity, but by the end of the 40s, Nancy was barely keeping up appearances. The pair had three children together, Nancy, Frank Jr,, and Tina, but even that could not prevent the relationship from breaking down by the start of the next decade.

Nancy had slowly been worn down by the highly public accounts of her husband’s various affairs, but the breaking point came when Frank himself announced his love for another woman. Early in 1950, Frank admitted to Nancy that he had been seeing Ava Gardner, and intended to keep doing so. The pair were divorced on Valentine’s Day the same year. How romantic.

38. A new obsession

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Sinatra had many dalliances with celebrities over the years, but his obsession with Ava Gardner was different. The first time he ever saw her picture in a magazine, Sinatra became obsessed, and promised himself that he would one day ask her to marry him. When they met for the first time, Frank was smitten, but Gardner was initially unimpressed.

Sinatra continued to doggedly pursue Gardner for years, and she slowly began to warm up to him in response, captivated by his talent and sensitivity. By the time Sinatra announced his split from Nancy in 1950, Gardner was just as obsessed with Sinatra as he was with her, and the pair began planning a wedding.

39. A second marriage

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Sinatra and Gardner were married mere months after Sinatra divorced Nancy. In November, 1951, the pair officially tied the knot. Frank insisted that his marriage to Nancy had been over emotionally long before he even met Gardner, even if the public quietly doubted that story.

However, though Gardner and Sinatra were undoubtedly one of the most beautiful and in-demand couples in the entertainment world, their marriage was not as idyllic as the many gorgeous pictures of them together suggested. After sneaking around together for years, and Sinatra even going so far as to leave his childhood sweetheart for Gardner, there was a lot of pressure on the relationship.

40. An imperfect relationship

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In addition to the pressure of Sinatra leaving his family for Gardner, there were other strains being put on the relationship. Both parties loved their vices, and were fond of drinking heavily, gambling and getting into altercations with each other in public.

Gardner had been married twice before being wed to Sinatra, and she was torn between loving his sensitive and gentle personality and resenting it. She allegedly remarked to her second husband, Artie Shaw: “With him [Frank], it’s impossible… It’s like being with a woman. He’s so gentle. It’s as though he thinks I’ll break, as though I’m a piece of Dresden china, and he’s gonna hurt me.”

41. Completely speechless

The early 50s brought upheaval and instability for Sinatra. As his dramatic personal life began to make headlines more often than his music, and as new singers began to come up and gain prominence, things started to topple in several areas of Sinatra’s life.

Perhaps the most tragic was the death of Sinatra’s loyal publicist George Evans, who passed from a heart attack in 1951, the same year that Sinatra married Gardner. Whenever Sinatra dealt with personal difficulty or depression, he also suffered physical symptoms, such as painful throat haemorrhages and a total lack of voice. This only exacerbated Sinatra’s problems, as he would find himself unable to distract himself from his problems by working.

42. A gift for a gangster

Around this time, the rumours of Sinatra’s connections to the Mob also became even more inescapable, with the press latching on to several pieces of anecdotal evidence to show that Sinatra was friends with some powerful but dangerous people. One of the most speculated friendships was between Sinatra himself and Sam Giancana, a famous gangster who was the boss of the Chicago outfit from 1957 to 1966.

For a period of his life, Giancana was never seen without a sapphire friendship ring, and many alleged that it had been given to him by Sinatra, as a reference to Sinatra’s nickname Ol’ Blue Eyes. Similar stories abounded that Frank Sinatra also introduced Giancana to his long-term partner and mistress, Phyllis McGuire.

43. Insufficient funds

Sinatra’s career downturn was cemented when he realised that he was not selling out the huge rooms he could have filled just a couple of years prior. Instead of hoards of teenage girls rioting when they were unable to score tickets to his shows, Sinatra was struggling to fill small theatres designed to seat 1,200 people. This observation came with another, more problematic, realisation on its heels – Sinatra was about to make far less money for the year than he was accustomed to.

Sinatra’s sharp decline in popularity led to him being unable to pay his back taxes, and so he was forced to ask two separate record companies to front the money for him. One refused, while the other agreed to pay so he would not have to declare bankruptcy. However, both record labels also dropped Sinatra from their roster on the spot, believing that his career was over.

44. City of sin

Needing money, and needing it fast, Frank had to come up with a plan. Instead of playing in the wholesome mid-American venues he was used to, Sinatra instead made the leap and moved out to Las Vegas, where he believed he could make his money back much faster.

First at the Desert Inn and then at the Riverside Hotel, Sinatra began working as one of the first resident entertainers in Las Vegas. The decision did stabilise some of the cashflow issues Sinatra was having, but it only increased the public’s perception of the singer as hedonistic and self-absorbed. Meanwhile, he began to play in smaller and smaller venues, soon being unable to draw a crowd of more than 150 people.

45. Dropped by the label

By April 1952, Sinatra was playing the smallest shows of his career so far, flying between Las Vegas and Los Angeles and being asked to be the featured performer at the Kauai County Fair in Hawaii. Sinatra’s fanbase was dwindling, and his record label had definitely noticed.

Columbia began to remark that they could not even give away Frank Sinatra’s records, and the recording sessions he was brought in to do were fraught with trouble. Though his voice was thankfully back and intact, Sinatra was tense and embarrassed throughout the recordings, and his sour attitude was visible to everyone watching in the studio. The next year, in 1953, Sinatra was dropped by both Columbia and MCA.

46. A tentative comeback

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The glimmer of hope that signalled the distant prospect of the Frank Sinatra revival was the movie From Here to Eternity. The romantic war drama starred Burt Lancaster and Montgomery Clift, but featured Sinatra and Donna Reed in supporting roles.

The film was an instant hit with both audiences and critics, and many remarked on Sinatra’s performance specifically, with Newsweek stating: “Frank Sinatra, a crooner long since turned actor, knew what he was doing when he plugged for the role of Maggio.” The reason Sinatra was given the part caused endless speculation, with most agreeing that Ava Gardner had used her Hollywood influence to ensure that Sinatra got an audition.

47. Winning over the Academy

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Sinatra didn’t just win over critics and audiences with his performance in From Here to Eternity, he also impressed the Academy. Sinatra won the Oscar for Best Supporting Actor for his work on the film, with Donna Reed also winning an Academy Award for Best Supporting Actress.

As if that were not enough, the film also picked up two more huge Academy Awards: Best Picture and Best Director for Fred Zinnemann. From Here to Eternity also took home Oscars for Best Screenplay, Best Cinematography for a Black and White Film, and Best Film Editing. Not a bad movie to stake your comeback on.

48. Inspiring a classic

Despite the award giving Sinatra’s reputation and own self-esteem a much-needed boost, not everything was on the up and up. Though the more popular narrative was that Ava Gardner had used her pull to secure Sinatra a role in the film, not everyone was convinced that it was her doing.

The rumour of Mob connections that had plagued Sinatra throughout his life reared its ugly head again, with speculation that Sinatra had paid a gangster to threaten director Fred Zinnemann with physical violence if he was not cast in From Here to Eternity. The rumour even went on to inspire the character of Johnny Fontane in The Godfather.

49. A second broken heart

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Just as his career was back on the up and up, Sinatra’s personal life came crashing down around him once again. After an especially tumultuous period between Sinatra and Ava Gardner, even by their own standards, the couple announced they were separating in 1954.

The pair were not officially divorced until 1957, as both had huge, complicated estates and a number of affairs to get in order, but their romantic entanglement was done. After a cooling-off period, however, Gardner and Sinatra did remain fast friends, with Sinatra often pulling strings in his more successful years to get Gardner involved in promising projects. As Ian McKellen would remark years later: “If you had married Sinatra, you didn’t need an agent.”

50. A new golden age for Frank

Despite his personal life remaining somewhat shambolic, Sinatra spent the mid-1950s working harder than ever before, hoping to capitalise on the success of From Here to Eternity and gain momentum. In 1955, Sinatra released his first 12 inch LP, named In the Wee Small Hours, which has gone down in history as one of the first concept albums to maintain one thesis statement all the way through.

In the same two-year period, Sinatra embarked on his first-ever tour of Australia, and recorded Songs for Swingin’ Lovers, considered by fans to be one of his best albums. The record featured a cover of Cole Porter’s song I’ve Got You Under My Skin, and Sinatra took exceptional care recording. As Cole Porter was Sinatra’s childhood idol, Sinatra recorded the track with a 56-piece symphonic orchestra, and made sure to do 22 separate vocal takes.

51. Warming up the Cold War

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So many rumours were flying around regarding Sinatra that at points they seemed contradictory. For every gossip column alleging that Sinatra was in the pocket of the Mob, others said that he had communist sympathies and was anti-American, a particularly damaging rumour that reduced his influence in certain political spheres.

This rumour was not exactly put to bed in 1959, when Sinatra was chosen to be the master of ceremonies at a luncheon attended by Nikita Khrushchev. Sinatra performed for the leader of the Soviet Union, and even shook his hand, as part of an effort to de-escalate the Cold War and bring Russia and America back into civilised conversation.

52. A Presidential friend

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Just like his mother before him, Frank Sinatra was a staunch Democrat for much of his life, and was vocally supportive of a number of progressive causes. In particular, Sinatra harboured a great amount of admiration for John F. Kennedy, and personally endorsed him and campaigned for him to be President.

Once Kennedy was elected, the two became close acquaintances, with Kennedy opting to stay at Sinatra’s mansion any time an official visit or state event called for him to be nearby. Kennedy’s friendship was also a great boon to Sinatra, as it increased his reputation as an all-American singer that the public could rely on and trust.

53. Divided loyalties

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Even though Sinatra admired Kennedy greatly, and Kennedy’s friendship much improved Sinatra’s public image, there was one reason that Sinatra occasionally came into conflict with JFK. While President, one of Kennedy’s biggest initiatives was empowering the police to take down the Mob, which was reportedly problematic for Sinatra for obvious reasons.

According to the rumours, the Mob were unhappy with Sinatra’s connection to and fondness for the whole Kennedy family, and frequently pressured Sinatra to distance himself from them. However, Sinatra continued to appear publicly with JFK and his family, until one day the President made his own loyalties clear.

54. A presidential snub

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Despite Sinatra being John F. Kennedy’s most vocal celebrity supporter, and even being invited to headline Kennedy’s inaugural ball when he was elected, Kennedy did eventually deal Sinatra a very public snub. The reasons why are unclear, but when Kennedy visited California in 1962, he did not stay at Sinatra’s mansion as usual.

Whether it was due to the increasing ubiquity of rumours about Sinatra’s Mob connections, or simply because the mansion was not deemed safe enough, Kennedy instead decided to stay with singer Bing Crosby. Unfortunately, Sinatra took deep offence to the President staying with one of his musical rivals, and didn’t exactly react in the most mature way.

55. Smashing up the good will

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Upon learning that President Kennedy would not be staying at his California mansion during his official visit, Sinatra decided to literally smash up the history the two had together. A helipad had been installed on the roof of Sinatra’s mansion specifically to allow for Kennedy’s safe arrival, and Sinatra took his anger out on it.

According to those who were watching nearby, Frank Sinatra mounted his roof and smashed up the concrete helipad with a hammer, by hand. This event marked the end of the close friendship between Sinatra and Kennedy, even though the singer remained a Democrat for a while longer before switching loyalties to the Republican party.

56. Striking out on his own

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By 1961, Sinatra decided he once again needed to take his career in a new direction. By this point, Sinatra had had cameo appearances in everything from Ocean’s 11 to Around the World in 80 Days, and had starred in huge hits such as Guys and Dolls and High Society. All together, Sinatra had appeared in over 35 films by this point.

This success led Sinatra to leave his record label in order to start his own. He created Reprise Records and marketed it to artists as a place where they could maintain creative control and eventually gain complete ownership of their own work, including publishing rights. This made the label hugely appealing, and its roster soon included Bing Crosby, Jo Stafford and Rosemary Clooney.

57. A horrifying phone call

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Just when everything appeared to be stabilising in Frank Sinatra’s personal life and career, his world was upended when he received some shocking news. On the evening of December 8th in 1963, his son, Frank Sinatra Jr., had been kidnapped from his hotel room in Tahoe.

Soon after a reeling Frank Sr heard the news, he received a personal phone call from the kidnappers responsible, who informed him that they would only be contacting him via public telephone boxes from now on, and laid out their demands.

58. A ransom demanded

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As expected, the kidnappers had targeted Frank Sinatra Jr for a reason: they wanted his father’s money. When pushed to put a number to their demand, the criminals insisted upon $240,000 of Sinatra’s fortune, about two million dollars in today’s money.

Curiously, when a panicked Frank Sr offered closer to three million dollars to ensure his son’s safety, he was refused. The kidnappers insisted on their original figure, and would not agree to either a penny more or a penny less. Frank frantically gathered the money and prepared to make the trade, but it never came to that.

59. A lasting impact

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In the end, Frank Sinatra Jr was released just two days after he was captured, and it was not necessary for Frank Sr to pay the ransom. However, despite the situation being resolved without any money changing hards or anybody getting hurt, it did have a huge personal effect on Sinatra himself.

Given that his son’s kidnappers told him that they would only communicate with him through public payphones, Sinatra spent the two days that his son was missing carrying rolls of dimes around in his pockets, so that he would always have the necessary currency to pay for a phone and pick up the phone. Even decades later, this habit remained with him.

60. Pleading insanity

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After Frank Sinatra Jr was released unharmed, it did not take long for the authorities to find the culprits. The whole team behind the kidnapping were immediately arrested and found guilty, but none served very long sentences. Part of the reason why was the odd details of the group being unwilling to accept more money, which didn’t seem to match their motive.

This odd choice began to make more sense when the ringleader of the gang pleaded insanity, and explained that he had not been of sound mind when he set up the scheme. The ringleader went on to win an appeal claiming that he was legally insane, which reduced his sentencing even further.

61. A May-September Romance

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In the years following his tumultuous relationship with Ava Gardner, Frank Sinatra continued to have a number of high-profile flings, but nothing as serious as his previous two marriages. After breaking off two engagements, one with actress Lauren Bacall and one with dancer Juliet Prowse, Sinatra seemed to step back from the dating scene. That is, until he met Mia Farrow.

Mia Farrow was 30 years Sinatra’s junior, but the two were infatuated with each other instantly. The relationship was filled with red flags from the beginning, with Farrow saying that she “behaved like a stroppy teenager” when she was with him, and Sinatra making allusions to her giving up on her acting career. Nevertheless, the two pursued the relationship.

62. Giving up on your dreams

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A little while into their relationship, Frank Sinatra announced his intention to marry Mia Farrow, but the proposition had a condition attached. Sinatra made it clear that if Farrow wanted to tie the knot with him, she would have to step back from the spotlight and abandon her acting career.

After a lifetime of being in high-profile and volatile relationships with other performers, Sinatra concluded that the only way to maintain a secure and happy marriage was to require his bride to step away from professional commitments. Shocking the media, since her star was very much on the ascendant at the time, Farrow agreed to leave the entertainment business and marry Sinatra.

63. An award or a marriage?

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Farrow initially kept her promise, living the quiet life and spending her days as a devoted housewife for around two years. Even though her friends revealed that she was bored and found the lack of work and stimulation difficult, Farrow committed to the life she had agreed to. That is, until Rosemary’s Baby rolled around.

Farrow was offered the now legendary part of Rosemary Woodhouse, and Sinatra tentatively agreed to let her shoot the project, despite feelings of uncertainty. However, when production overran by just a few days, Sinatra allegedly flew into a rage. Sinatra served Farrow with divorce papers while she was still on set, and the pair finalised the divorce in August 1968. For the rest of Sinatra’s life, the two would remain friends, and they even allegedly continued an on-off affair – Farrow would later hint that her son with Woody Allen, Ronan Farrow, might actually be Sinatra’s – but in total their marriage lasted little more than two years.

64. The fourth and final marriage

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After his relationship with Mia Farrow ended, it took almost a full decade for Sinatra to find someone he could be with for the rest of his life. In 1976 Sinatra married Barbara Marx, a woman who was no stranger to life in the public eye, not to mention high-profile marriages. Marx’s previous marriage had been to Herbert ‘Zeppo’ Marx of the legendary Marx Brothers, so she was well-equipped to handle Sinatra.

Though their relationship was not without drama either, it did represent both of their longest marriages. Barabara would later say of Sinatra that “he would snap at anyone for the slightest misdemeanour” but would have post-show highs that would take him “hours to come down from”, that he would spend in a state of “childish delight”.

65. A lifelong love

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Barbara and Frank Sinatra were married for 22 years, until Sinatra’s death in 1998. Barbara went on to live until 2017, but she never married anyone else, or had any other serious relationships. Even after Frank had died, she continually referred to him as “the love of [her] life”, and maintained total control over his likeness and name.

Frank’s first wife, Nancy Barbato, died just a year after Barbara in 2018, at the age of 101. Sinatra paid for the hospital bills of all of his wives when they needed it, even insisting on paying for Ava Gardner to see a specialist before she died in 1990.

66. Keeping clean

Despite her enduring love for him, Barbara Sinatra never had any issues with spilling the truth about her relationship with her husband. Barbara was consistently outspoken about details of their life together, from how Sinatra’s perfectionism affected her to the way he was consistently critical of his voice following shows in his later years.

However, one of the weirdest details that Barbara shared about her late husband was the fact that he was obsessed with cleanliness. According to her, in his later life, Frank would be in and out of the shower constantly, sometimes getting under the water 12 times a day in an attempt to feel clean and fresh.

67. A tragic plane crash

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By 1977, Sinatra was consistently performing in Vegas, specifically at Caesar’s Palace. His mother Dolly Sinatra, who was around 81 years of age at the time, had arranged to come and see him perform, making the trip from where she still lived in New Jersey. Dolly had come to see her son perform in Vegas before, and had developed a taste for gambling, even becoming notorious to those who worked at the casinos for her tendency to rig the slot machines so she could keep winning.

Unfortunately, this time, Dolly Sinatra did not make it to Vegas. The small private plane she was travelling in crashed over the mountains on the way to Nevada, killing everyone aboard. It was later discerned that the plane had crashed due to an error on the pilots’ part, something which enraged and saddened Frank.

68. A beachside recovery

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Always a consummate professional, Frank attempted to complete his run of shows at Caesar’s Palace, but the grief was understandably too much to bear. After just two shows out of his scheduled appearances, Sinatra cancelled all future shows, and retreated to Barbados in order to grieve, rest and recover.

His mini-retirement only lasted two months, during which he made no public appearances and asked for privacy from the press and from his fans. After that two-month period, Sinatra came out of isolation in order to perform for Princess Margaret at an official royal event in London.

69. The biggest hit of his career

Despite being many decades into his career by the late 70s, the biggest hit of Frank’s life was still on the horizon. Sinatra’s rendition of New York, New York, which he released in 1977, became one of the most iconic songs. It cemented his legendary status, and was considered by many to be the last high point in terms of showcasing his vocal ability.

Unfortunately for Frank, not everybody was happy with his rendition. The one person he really wanted to impress, the song’s original author, Fred Ebb, was not pleased with Sinatra’s take on the song. Ebb’s reasoning was simple: Sinatra had a reputation for adding his own lyrics and moving words around in the recording booth, which often infuriated the songwriters he worked with.

70. An unwanted fan

At the height of his popularity, Sinatra was probably the most beloved crooner on the planet. He had legions of fans and, unfortunately for him, that meant being admired by people he probably wished did not admire him. Specifically, Sinatra had a fan in Lee Harvey Oswald, the man who had killed his friend John F. Kennedy.

According to court records, Oswald admitted to watching Sinatra’s film Suddenly a few days before the infamous incident. Sinatra, having been a close friend and avid campaigner for JFK, was deeply disturbed to hear this. To assuage his own guilt, Sinatra asked United Artists to pull the film from circulation entirely.

71. A Republican roast

From the mid-70s onwards, a staple of television entertainment was The Dean Martin Celebrity Roast. The show, which ran from 1974 to 1984, was patterned on far more infamous and informal roasts held at the New York Friars’ Club. Guests included everyone from Bette Davis to Bob Hope, and George Washington was even roasted posthumously.

Frank Sinatra was roasted in 1978, and the panel of roasters consisted of Red Buttons, Gene Kelly and Don Rickles, among others. However, perhaps most unusually, Sinatra was also roasted by Ronald Reagan, who had also roasted George Burns and Bob Hope. Reagan had already had his time in the hot seat, having been roasted in 1973 when he was still a governor.

72. A political 180

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Sinatra grew up in a committed Democrat household, and continued to align himself with the Democratic party for most of his life, even campaigning for JFK for several years. However, his political affiliations changed completely when Ronald Reagan ran for President, as the pair had been great friends throughout Reagan’s Hollywood years.

Sinatra became a devout Republican and campaigned on Reagan’s behalf. He later said that his changing allegiances were a result of the Democratic party’s shifting values and policy focuses, which made him feel alienated. Sinatra even became Reagan’s official fundraising ambassador, quite a shift from his earlier progressive years.

73. The infamous biographer

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As Frank moved closer to his twilight years, rumours swirled about who would be the first author to compile a biography of his life. Out of all the names that people speculated about, only one was accompanied with an undertone of fear and infamy, and that was Kitty Kelley.

Kitty Kelley had previously written unofficial biographies for many other Hollywood stars, such as Jacqueline Kennedy Onassis and Elizabeth Taylor. Kelley was famous for digging up dirt about her subjects, and so many were curious about what she could reveal about the life of Ol’ Blue Eyes. Others were aware of her reputation as a “professional sensationalist”, and were convinced that any biography she wrote about Sinatra would simply make things up out of whole cloth.

74. An unsuccessful lawsuit

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Sinatra was aware of Kitty Kelley’s reputation as a biographer, and wanted nothing to do with it. As soon as rumours began to mount that he was Kelley’s latest target, he vocally objected, and even threatened to take the author to court to prevent her writing about him. When Kelley officially announced her intention to write about Sinatra, his threats became reality.

Sinatra spent two million dollars on a lawsuit to stop Kelley’s book being released, with the contents of the biography including details about his marriages, his various affairs and his connections to the mob. However, Sinatra later withdrew the lawsuit without giving a reason why, leaving Kelley free to publish the book entirely uncontested.

75. Doing it her way

His Way: The Unauthorized Biography of Frank Sinatra, was released in 1986. Once released, the book instantly reached number one on the New York Times Bestseller List, and also claimed the number one spot on bestseller lists in England, Canada, Australia and France. Kelley’s reputation as an author, which had previously focused on her tendency towards gossip and exaggeration, was now of a crusader for truth.

In the Washington Post, book critic Johnathan Yardley wrote: “His Way is such an improvement over her two previous books … that comparisons border on the pointless.” Despite the high praise, many of the anecdotes in His Way were also later proven to be false, such as the info Kelley received from Judith Exner, who claimed to be an ex-girlfriend of Frank Sinatra, a mistress to JFK, and a mistress to mafia leaders Sam Giancana and John Roselli.

76. Getting the gang back together

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In the late 80s, Sinatra expressed a desire to get the ageing Rat Pack back together. Sinatra had suffered a decline in his health throughout the decade, which his daughter Nancy blamed on the publishing of Kelley’s book. Despite not being fighting fit, Sinatra was determined to reunite with all his old friends and go on tour, so the dates were booked.

Unsurprisingly, the tour created a huge amount of buzz, and everyone was excited to see these ageing crooners working together again. Unfortunately, the tour was not going to be the smooth sailing victory lap that all of the performers were envisioning.

77. An uneasy alliance

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The Rat Pack reunited tour had problems from the very beginning. Though everyone was on edge thanks to the pressure of having to perform at their very best, most of the tension lay between Frank Sinatra and Sammy Davis Jr. For the majority of the tour, Sinatra refused to talk to Davis, thanks to Sinatra’s objection to Davis’ use of illicit substances.

Sammy Davis Jr also harboured animosity towards Sinatra. At the time, Davis was going through some financial difficulty, and claimed that Sinatra had promised him millions in exchange for doing the tour. Davis also claimed that he was receiving none of that money, and that Sinatra was skimming funds off of the top of the profits for himself.

78. Burying the hatchet

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The uncomfortable dynamic between Frank Sinatra and Sammy Davis Jr changed completely in 1989, when Davis was diagnosed with throat cancer. His diagnosis coincided with the end of one of the legs of the tour, so Davis was free to rest and pursue treatment. As a gesture of goodwill, Sinatra presented Davis with a gold watch on the last day of the tour, to thank him for his involvement.

Sammy Davis Jr died less than a year later in 1990, at the age of just 64. The legendary singer was buried with the gold watch that Frank Sinatra had bought for him at the end of the tour, forever immortalising him as one of the Rat Pack, and a great personal friend to Sinatra.

79. Losing the battle

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Sinatra’s health in the 80s unfortunately worsened, with the artist becoming increasingly frail. By his final concerts, Sinatra would frequently forget the words to his songs, and even become confused on stage. In addition, he was also dealing with a litany of health issues, from heart problems and breathing issues to pneumonia, dementia and bladder cancer.

Everything came to a head when Sinatra was rushed into care following a heart attack in 1998, with his wife Barbara by his side. The story goes that Barbara held his hand and told him to keep fighting, to which he heartbreakingly replied: “I’m losing”.

80. A last goodbye

Frank Sinatra passed away in May of 1998, with his wife Barbara by his side. At first, it seemed as though none of his nearby family could get to him on time, but later a darker narrative emerged. Sinatra’s daughter Tina later alleged that Barbara hadn’t contacted her or her siblings when their father had gone into hospital, and instead left them to find out too late.

As if that was not bad enough, Tina also claimed that Barbara Sinatra had done this on purpose, in order to be the lone tragic and heroic figure at Frank Sinatra’s side. This allegation caused a rift between Barbara and Frank’s children following his death, as they could not forgive the fact that they did not get a chance to say goodbye.