On May 14, 1998, the greatest entertainer of the 20th century died in Los Angeles. This is his incredible story.
Even a quarter of a century after his death, his hits like “My Way”, “Strangers in the Night” or “New York, New York” are still known worldwide. Less well known are the shady and dark sides of the exceptional American entertainer.
Frank Sinatra (1915-1998) started his career in the dying swing era of the late 1930s. From a young age, the son of Italian-American parents trundled through the bars in his hometown of Hoboken, New Jersey.
From there, the later world star already had an optimal view of the Manhattan skyline on the other side of the Hudson River. Only a short time later, the young singer crossed the bay to become a legend.
The big breakthrough
After his first small radio appearances and concerts, he had his big breakthrough in 1939. The band leader Harry James (1916-1983), who was very well known at the time, discovered the young man’s singing talent and immediately engaged him as the lead singer of his big band.
Just one year and one band change later, Sinatra landed his first number one hit with the melancholic song “I’ll never smile again”. From then on things went straight up – musically and privately.
Legendary Daughter: Nancy Sinatra
Newly married to his childhood sweetheart Nancy Barbato (1917-2018), he became a father for the first time in 1940. His first daughter Nancy Sinatra (82) would later follow in his musical footsteps and also achieved some fame as a singer.
From 1943 he had a permanent recording contract with the label Columbia Records and quickly became the most successful singer on the continent with numerous hits. As the new star of the American war generation, he was soon everywhere. Especially with his numerous own radio shows, such as “Frank Sinatra in Person”, he reached a steadily growing fan base.
First mass hysteria in modern music history
On October 12, 1944, the young pop star triggered the first mass hysteria in modern music history. On the occasion of a concert in New York’s Paramount Theater, more than 30,000 mostly female fans flocked to Times Square and besieged the building, screaming hysterically. Only hours later did the police manage to get the situation that has gone down in history as the “Columbus Day Riot” under control again.
At the first peak of his long career, Sinatra entered the film business with great success as an actor. For his leading role in the film “The House I Live In” he received his first Oscar in 1945, which was later to be followed by three more.
Career break in the early 1950s
At the beginning of the 1950s, Sinatra’s career suffered a brief slump. After his divorce from Nancy Barbato, the former singing cleaner drew attention to himself with various affairs. His subsequent marriage to film diva Ava Gardner (1922-1990) was short-lived. After developing vocal cord problems, he even lost his record deal in 1952 and seemed to have come to the end of his musical career.
Pretty soon, however, Franky Boy managed to get his career back on track and continue to build his international fame. He initially focused primarily on the film business and received another Oscar for his role in the film “Damned to All Eternity” in 1954. With “The Frank Sinatra Show” he got his own TV show, but he also started again musically and even founded his own record company.
“Strangers in the Night”
“The Voice”, as it was now respectfully called, had its biggest hits in the 1960s. In 1966 he had the greatest commercial success of his musical career with “Strangers in the Night”. In 1968, he even upped the ante with the release of the iconic “My Way.” With his legendary “Rat Pack”, a circle of close friends such as Sammy Davis Jr. (1925-1990), Dean Martin (1917-1995) and Joey Bishop (1918-2007), he celebrated great success on the stages of Las Vegas and earned good money.
Although he officially retired from the stage in the early 1970s, he soon returned and continued until shortly before his death. The best-known hit of this phase is “New York, New York”, the world-famous anthem for the city in which his career began.
Did Sinatra Hire a Mafia Killer?
After his death, some of the entertainer’s less glamorous sides came to light: His temporary alcohol and drug addiction became known, and Sinatra’s connections with the American underworld came into focus. It was repeatedly said that he was involved in criminal activities, but this could never be clearly proven.
For example, the singer and composer Paul Anka (81) claimed that Sinatra tried to hire a hitman through his mafia connections in the 1960s to kill a casino manager for him. The reason: After a change of ownership, the guest of honor should no longer receive free chips when visiting the casino…
The secret of the iconic Sinatra hat
After the death of the legendary crooner, the secret was revealed as to why he almost always wore a hat in public from the mid-1960s. The reason was quite simply the singer’s thinning hair, who also liked to wear a toupee during sweaty performances.
I am an author and journalist who has worked in the entertainment industry for over a decade. I currently work as a news editor at a major news website, and my focus is on covering the latest trends in entertainment. I also write occasional pieces for other outlets, and have authored two books about the entertainment industry.