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December 2019 marked the 104th birth anniversary of Frank Sinatra. Years later, there’s still so much to learn from the music that the late crooner left behind

Words Yvonne Jacob

A cigarette burning away in one hand and bourbon in the other, immaculately dressed in the finest clothes, wearing mirror-like shiny Oxfords on his feet and always surrounded by beautiful women swooning over him, every man dreamt of being Frank Sinatra, the OG gentleman. Although he was known to be an emotional man who sang lyrics that sounded intense and even achingly personal, he had a reputation of having ties with mobsters and the ladies loved it. He had a strong presence on stage, a big voice presented in a grand manner, the ultimate entertainer of his era.

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His songs made women melt like butter on warm toast and also gave the “tough guys” a free pass at having their well-deserved moments of weakness. Sinatra's songs were what lovers listened to as they turned their nights into day.

Sinatra began his musical career with bandleaders Harry James and Tommy Dorsey in the swing era. By ‘50s he moved to Vegas, where he became one of the best residency performers as part of the Rat Pack. He went on to become an actor and producer and his big entertainer persona got him into the spotlight, also bringing in the age of self-expression.

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This was his I’ve Got the World on a String phase, the peak of his career. The phase was bound to pass and Sinatra endured bouts of melancholy that began to slowly infect his music with bitterness. This phase brought out his tragic vision of life through his albums In the Wee Small Hours, Frank Sinatra Sings for Only the Lonely and Where Are You?.

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Despite the personal conflicts that led him to where he was at the time of his demise, whenever his music comes on, Ol’ Blue Eyes doesn’t fail to entrap you with his unadulterated understanding of music and lyrics, old school style. When winning a woman’s heart was through music and not all about a poorly put-together DM.

Frank Sinatra was the ultimate entertainer of that era.