Sinatra is considered by many to be the greatest entertainer of the twentieth century. His recordings came to epitomize American popular singing at its finest, with a style that maintained fidelity to a song’s lyric and mood while imbuing it with subtle elements of jazz beat and phrasing ranking among the most famous singers in the history of pop music. Tremendously influential on 20th century music, Sinatra set his own ground rules and as a song stylist, was peerless. Sinatra's talent came from combining a vulnerability in a gritty image as one of the regular neighbourhood guys that made it big due to his distinctive phrasing in singing, learnt from Tommy Dorsey’s phrasing with his trumpet. Sinatra also developed his style, copying teenage idol Bing Crosby, as did Dean Martin and many of the crooners of his era. He wasn’t only a crooner, Sinatra adopted the name Swoonatra by fans, as he was highly popular with teenage girls or “bobby soxers” as they were called in his day, but this wasn’t always the case. In the early 40’s Sinatra’s career was up and down, and for a period of time Sinatra paid girls to cheer and applaud him, to help lift his success and appeal.

He was scarred on his ear, neck and cheek – and his eardrum pierced – all by the clumsy use of forceps at birth, which caused him to be teased as a child. Unfortunately because of the troublesome birth and the damage it caused to his mother’s body, Dolly could never be able to have another child.

Volatic, stubborn, vengeful but also extremely loyal, Sinatra was generous, gentlemanly and lead a massively self indulgent lifestyle along with a humble career, that saw him redefine the image of an idol. Sinatra had the embodiement of the swinger and was the quintessential middle aged playboy stereotyped with the hard drinking, high living clique. Although Sinatra was a drinker, he had a habit of leaving drinks everywhere, giving the impression that he was a heavy drinker, why by rights, he wasn’t at all but was known to over indulge in alcohol on many occassions. Sinatra, a smoker of many years, never inhaled when smoking, afraid that it would damage his voice – the one thing that was reinforced as being eternally precious to him after his throat hemorrhage in the 50s. Frank felt a trickle at the corner of his mouth whilst performing one night. Thinking it was saliva, he wiped it away with his white hankerchief. It was blood. Later, it would be diagnosed as a submucosal hemorrhage

A man of extreme contradictions, he inherited a quick temper from his mother Natalie and adopted a hot temper and lashed out – punching and what have you – at anyone or anything that set him off, which made his outings front page news which didn’t exactly please MGM studios whom he was under contract with since 1944 that was eventually cancelled by Louis B Mayer. According to Peter Lawford, one night Sinatra was in a rage, he pushed a girl through a plate glass window and almost severed her arm from her body. "When somebody called me a 'dirty little guinea', there was only one thing to do - break his head". These words came from the mouth of Frank Sinatra. It is well known that Sinatra assaulted and almost killed Frederick R. Weisman (the president of Hunts Foods) by smashing him over the head with a telephone in the Polo Lounge of the Beverly Hills Hotel on June 8, 1966. The reason? A petty argument between strangers about the boisterousness and rude language being used by Sinatra and his party. Due to subsequent anonymous threats to Weisman and his family, no charges were ever brought against Sinatra. Sinatra’s arrogance and temper were always his own worst enemies. His true life story is not about a man who did things "His Way" it's about a man who couldn't control himself and constantly tried to weasel out of taking responsibility for his own (self-)destructive actions.

Mr. and Mrs. Tony Bennett and his wife witnessed a 1967 incident at the Fonainbleau hotel coffee shop in Miami where Sinatra insulted a janitor who asked for his autograph. Sinatra called his "dago secret service" then punched out the janitor and left him bleeding on the floor. After making jokes in his Las Vegas act about the age difference between Frank Sinatra, 50, and his new bride Mia Farrow, 21, comedian Jackie Mason was repeatedly warned by friends of Sinatra to drop that material from his routine. Three bullets were pumped into his Vegas hotel room, shattering the glass doors and lodging in the mattress of his bed. Later, Mason had his faced re-arranged (including broken nose and cheekbones) by a man who repeated the warning about the Sinatra jokes.

He may have been hot tempered, but was also particularly sympathetic to the victims of automobile accidents. When he found out that a young girl (the niece of a music publisher) had been paralyzed ion a car mishap and was a fan of his, he went to the hospital and sat with her for hours, talking to her even though she could not respond. When Lee Remick’s husband was in a car crash, Remick and her mother flew to LA and stayed at the Beverly Hills Hotel for a week until she was told he would live. When they checked out, they learned that Sinatra had paid the hotel bill. She could not remember having ever met Frank.

For as many girls who swooned over him, there were that many problems in his personal life. He was a man of contrasts. The same man who sent teenage girls into faints was known for his brawls in public. He was a star with a lot of problems, and one of the biggest issues was his use of women. From his upbringing with his mother to quarrels with his many lovers, he and women were like gasoline and matches. Although Sinatra is an icon of the twentieth century, he had more than his fair share of a superstar's personal problems.

No one could bear a grudge like Frank and it was worse if there was gossip involved, as he would believe gossip before he would his best friend. George Jacobs was at the Candy Store which was a disco in Beverly Hills, where he came across Mia. After a few dances he left her and went home. The next afternoon when he reported for work at the Palm Springs compound, he found his key didn’t fit the lock. He had been dismissed from Sinatra's service, never to re enter, nor try to contact him, with no explanation, no apology no nothing.

Although he had erratic sides to his personality, it was the Rat Pack that bought out his arrogant and self absorbed side, as his fame was at an all time high and he was taking advantage of that and milking it for all it was worth. Sinatra ruled the world on his own terms. The one thing Sinatra hated was to be alone, as he became anxious and fearful and bored easily. He was like a hyperkinetic kid - he couldn’t sit still, and he couldn’t be alone. He’d astonish his co-stars by showing up on the set at 7am, straight from some all-nighter, dressed in his tux, his tie undone, and his stubble starting to show, duck into make-up, and come out an hour later as fresh as a daisy and in perfect control of his part. This need not to be alone may explain why Sinatra had so many marriages, and developed the Rat Pack. Due to this fear, he forced people to stay up until early hours of the morning with him, to keep him company and would scald anyone who went to bed early or tried to get out of his gatherings at night. His acquaintances who sat up with him every night until he could go to sleep; endured the continual brawls and cherry bombs and drinking until the last bottle was empty and the last song sung agree that Frank was a sick guy in many ways, and that sickness became a heavy burden for those close to him after a while.

Even though he hated being alone, he didn’t like to be crowded and had specific tastes when it came to people and especially women. Sinatra was prudish or old fashioned when it came to women that he wanted to socialize with, and the women in his family. The prostitutes and chorus girls that he had frequent affairs with, he accepted them for who they were and their less than virginal appearances, but was very strict on his children and very picky about women he had in his life that were there to stay, preferring girly girls as he didn’t like women who smoked, wore makeup and exploited their sexual appeal. His children rarely came to the Compound, which was Sinatra’s “bachelor pad”, that he didn’t want them to see. When they came down to Palm Springs, he made me get rid of all evidence of whatever women visitors had been around. He was very prudish and old-fashioned in thinking he could shield his children from his playboy reputation.

Sinatra was a very vain man, always primping himself and showering at least 4 times a day. Some say that he had a cleanliness complex, that he inherited from his mother Dolly. When he began to bald, he painted his bald spot and always wore wigs, to deceive the public in believing that he wasn’t loosing his hair. He hated going bald, because it was the one thing he couldn’t control. Frank was always paranoid about his breath and would repeatedly ask women if they could smell booze or cigarettes on his breath.

Sinatra was a highly credited singer, however, his acting career didn’t exactly move people as much as his singing did. Humphrey Bogart is quoted as saying that he felt Sinatra lacked the maturity and dedication necessary to translate his raw talent into a first rate movie career. Shirley MacLaine put forward the theory that some deep rooted fear of failure held Frank back from giving his best to most performances, providing him with the handy get out clause that, should his work be criticized, he could always riposte with the claim that he hadn’t really tried. Frank was notorious for his impatience with the process of film making. He had a reputation for set moodiness and unpredictability, known to rip chunks out of the script in fits of rage, leaving the writers to fill the gaps. Sinatra carved himself a niche in cinema history that amounts to far more than prancing about in a sailor suit for MGM in “Anchors Aweigh”, by picking up an admittedly undeserved Academy Award for “From Here To Eternity” and playing crooks, cowboys and gangsters with his Clan mates.

In 1950 on Valentines Day, the separation was announced between Nancy and Sinatra and a divorce granted one and a half years later, which saw him remarried one week later to Ava Gardner. Frank’s career was at an all time low and papers were dubbing him Mr Ava Gardner. Frank was borrowing money from Ava and following her around trying desperately to get his career back on track. When Ava and Frank divorced, Frank boozed, brawled and played the field to satisfy himself by getting revenge on Ava. He dated Natalie Wood, Marlene Dietrich and Lauren Bacall to name a few. He did everything in the world to get over losing Ava. One of his favourite songs was “I Can’t Get Started With You” and he always had her in mind when he sang it. Every love song he sang was for her, and every woman he had was an attempt to make him forget her. Sinatra had many paramours but always denied them. The press was always anxious to leak secrets of his affairs. They ripped him apart because they considered his carousing with women while married to be his biggest sin. According to some press reports, "he appeared to be making an almost heroic effort to bed the female population of an entire industry."

Frank Sinatra was known to be quite the romantic. He would call a woman, say "I love you", then hang up. He would send flowers every day and he gave lavish gifts very often. The staples were bracelets and necklaces of diamonds, but he often gave out-of-the-ordinary things as well. He gave a horse and pearl- handled pistol to Mia Farrow and a shower bath to Ava in the African jungle where she was filming a movie. However, he could also be cruel, once he had his fill of them, he would drop them quickly. Women were drawn to him and he loved it. This was a downfall for him because as soon as he had had his thrill, the conquest, he would leave them high and dry. Gardner was the jealous type and she often accused Frank of cheating on her. She said that he made it clear that if he was going to be accused of cheating, there would come a time when he decided he might as well be guilty. He called Gardner to say that he was in bed with another woman. Tony Curtis says that Frank wasn’t a womanizer, rather he was womanized. Women literally threw themselves at him.

Frank was one of the few regular visitors to the Bogart household during his friend and mentors battle with cancer. His emulation of Bogart exhibited itself for more in his life than his art. A proud member of his Rat Pack, Sinatra formed a similar clique after his death and dated his widow Lauren Bacall. Frank worshipped Bogie, and even copied Bogie’s wry and subtle swagger. Frank was devastated when died.

After a photo was taken of Peter Lawford and Ava Gardner out on a supposed “date” Frank was outraged and didn’t talk to Peter for 5 years. He declined invitations to parties Peter, or the crumb, was to invited to. Pat, Peter's wife, was mad about Frank and wanted to meet him. It was through Pat's desire to meet Sinatra, Peter's Kennedy Connection and ownership of the rights to the film “Oceans 11” that Sinatra started talking to Peter again in 1958, with Sinatra apologising to Peter one night, whilst drunk, for his behaviour and over reaction concerning the Ava situation.

Mobsters were the only ones that gave Sinatra work and were his friends in his career low – or the Ava era before “From Here To Eternity.” Sinatra had a surprisingly nonchalant and flippant attitude towards crime. He theorized that it was impossible for an entertainer to work (let alone be the high rolling gambler he was) in clubs in Vegas in the old days without rubbing shoulders with crime figures who had financial stakes in such operations. He thought organized crime was glamorous, and had a strong acquaintanceship with the underworld and top dog Sam Giancana, the King pin who wanted the singer to intercede with JFK and RFK for special favours in the early 60s. Sinatra called George Jacobs George, but when he was being rambunctious, particularly with gangster friends with whom he liked to act as bad as possible, he’d call him spook. He called Dean Martin “wop, Gene Kelly “shanty”, Cary Grant “sheenie” and Jerry Lewis “jew” because he loved being the bad boy and insisted on doing the opposite of what was politically correct, except around Giancana, when he was on his best behaviour.

The scope of Frank's real life association with Giancana was documented by the FBI in 1962 and led JFK to cancel vacation plans to stay at his Palm Springs compound. In 1963 Sinatra’s ties with Sam led to the revocation of his gambling license at the Cal-Neva Lodge of which he was part owner.

Sinatra’s Rat Pack, was unlike Bogie’s social group. Bogie’s clan had class compared to Sinatra’s. The goings on of Bogie’s pack were private and confidential, whereas the attraction of parading the new summit group before a live audience proved irresistible for Sinatra. Sinatra and his pallies were so friendly that Sinatra financed the quartet of movies for the Rat Pack.

In 1959, there was a new president to be elected and Sinatra didn’t want another stuffed shirt running the country, vowing that the country needed shaking up. It was this thought that got a playboy elected to office and saw Frank criticized in the media. FBI wiretaps reveal that Sinatra apparently disbursed large mob donations in West Virginia that were used to pay off election officials and resulted in JFK becoming the 35th President of the United States. The relationship with the Kennedys was thought by Frank to be strong, but the JFK snub in 1962 convinced Frank that the Rat Pack had not only outlived its usefulness as a publicity gimmick, but had become a liability. Frank had to face the reality that there was no place in Camelot for wops. Enraged by the apparent snub from his most esteemed acquaintance, Frank took his wrath out on Peter. The Kennedy go between/alleged procurer immediately lost his scheduled roles for the Pack films “4 for Texas” and “Robin and the 7 Hoods” and was cast out from Frank’s circle forever.

His blacklisting of Lawford had been very effective as a number of producers in Hollywood wouldn’t use him either because of Sinatra's influence or Peter's involvement in Marilyn Monroe’s demise.

Mia Farrow, a young and upcoming star, was completely taken by Sinatra and would wait outside the studio for a glimpse at her idol. When they were dating, Dino joked that he had a case of scotch older than Mia, as she was barely an adult. Mia claimed that her love for Frank was more important than her emerging career and that she would quit Hollywood and marry Sinatra, which was what Sinatra wanted after Ava being the main bread winner in their marriage. Eventually she became bored and wanted to work as she was very ambitious, and along with Frank’s refusal to understand her generation (the hippy generation) and dislike of change, the marriage ended. He thought that the permissive youth culture was a threat to the American way, to his way in particular. He was notorious for being a rebel, for having affairs and partying. Suddenly when a new culture of people began to do the same, he was no longer unique. Mia put up with his capitalist pig, get a haircut attitudes for as long as she could.

Just how much pull Sinatra had in the entertainment industry was apparent around 1970, when Sinatra discovered that alleged solo Kennedy assassin Lee Harvey Oswald had watched his film “Suddenly” just a few days before the Dallas slaying on the 22nd November 1963. He withdrew “Suddenly” from circulation and it was banned from the USA and Britain from 1971-94.

Sinatra, like Sammy Davis Jr., didn’t want to let age slow him down and was the same drinking, partying playboy he was in his younger days, at his death.