Frank Sinatra has been and always will be one of the most remembered legends in the music world for his extraordinary voice, outstanding work, and eccentric attitude. Sinatra’s life, no matter how you look at it, is a rollercoaster of growth, success, disappointments, romances, and adventures. Today, to once again pay homage to the renowned artist, we have compiled some of his most remarkable anecdotes and experiences, which marked turning points in his career both as a musician and as a human being. Join us for a journey into the past to discover things you didn’t know about Frank Sinatra’s life!
A Lesson in Humility
Although he was not precisely a fan of rock music (which Sinatra considered an aberration to his ears), the artist performed a duet with the legendary rock singer Elvis Presley. Watch the duet. Both artists participated in a special televised event to celebrate Elvis’s return to the music world and to end their rivalry. Initially, Frank Sinatra showed no interest in meeting his rival but eventually agreed upon his daughter’s advice.
The gala they performed was a great success and helped boost both their careers.
The Importance of "My Way"
One of Sinatra’s most successful works, which gives its name to our lounge restaurant in Barcelona, is "My Way." The melody of this Sinatra classic is based on the compositions of French artist Claude François and his work "Comme d’habitude," a moderately popular song that captivated Sinatra.
At 50, Sinatra felt his career was stagnating due to the popularity of rock & roll, the rise of new youth idols, and his personal struggles. Just before planning his retirement, Paul Anka introduced the song to him, and that same night Sinatra began composing it. Listen to "My Way".
"My Way," unlike "Comme d’habitude," focuses on a man nearing the end of his life, bidding farewell without regrets and declaring he did it his way. Thanks to the success of this work, the artist abandoned the idea of retirement and made the song his life philosophy.
The Unexpected Son
According to his biography, when Frank Sinatra was born, his mother, Dolly Sinatra, was quite disappointed as she had eagerly hoped for a girl. Her plans were suddenly upended.
A Peculiar Relationship with Spain
Throughout his career, Frank Sinatra performed internationally, but there was one country he didn’t particularly favor: Spain. The artist experienced a series of unfortunate events that strained his relationship with the country. Every time Sinatra visited Spain, unforeseen mishaps and failures disrupted his concerts and scheduled performances.
Although the Franco dictatorship was in effect and complicated matters, much of his misfortunes were closely tied to his partner, Ava Gardner. Their relationship was filled with jealousy, lies, and extramarital affairs. In Spain, the couple eventually divorced, though they stayed in contact. According to acquaintances, their electrifying personalities were hard to manage.
A Very Special Gift for a Very Special Person
Among Sinatra’s great friendships was the legendary actress Marilyn Monroe. They were very good friends, and after Monroe divorced her last husband, Sinatra gifted her a dog to help her heal from her heartbreak. Learn more about Sinatra and Monroe.
Some rumors suggest they had a brief romance to console each other from their toxic relationships, especially since Sinatra’s tumultuous experience with Ava Gardner left a lasting mark on him. However, it is clear they supported each other during difficult times, solidifying a strong friendship. On several occasions, Marilyn rejected Sinatra’s romantic advances.
An Inspiration of Legend
While it’s true Sinatra maintained certain cordial relationships with various Italian mafia figures like Lucky Luciano, the singer himself admitted he was often involved in FBI investigations for crimes he was indirectly linked to. This fueled speculation that the mafia helped catapult Sinatra to stardom by taking care of his fiercest rivals, though this was never proven.
This controversial rumor inspired the character of Johnny Fontaine in the film The Godfather, released in 1972.
The Frank Sinatra Musical
To conclude our list of curiosities about Frank Sinatra’s life, theaters around the world annually stage a musical dedicated to his music and life experiences titled My Way: The Life of Frank Sinatra. Watch the musical. This theater production showcases his most popular songs and recounts the pivotal moments of his life. It’s a spectacle no Sinatra fan should miss in Spain. And don’t forget to try his special cocktail at My Way!