Renowned artist Tony Bennett died on July 21, at the age of 96. He was an iconic figure of the American Songbook and had an enduring career that spanned from performing with Judy Garland to collaborating with Lady Gaga. His publicist, Sylvia Weiner, officially confirmed his death to the Associated Press. Tony Bennett had bravely faced Alzheimer’s disease since his diagnosis in 2016.

Despite Tony Bennett’s towering successes in his career, he faced formidable battles behind the scenes. The advent of rock ‘n’ roll had significantly impacted the music industry, rendering many crooners obsolete. Consequently, Bennett’s records began to decline on the charts, much to the dismay of his record label, Columbia.

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During that era, Bennett’s main adversary was Clive Davis, a dominant figure in the music industry who assumed control of Columbia in 1967. Davis insisted that Bennett should record more contemporary songs, as he believed the singer’s repertoire was outdated and no longer resonating with the public. Bennett, on the other hand, was appalled at the idea of a non-musician like Davis being in charge of a music label.

Reluctantly, Bennett agreed to record modern pop songs for the 1970 album, which later became known as “Tony Bennett Sings the Great Hits of Today.” The pressure and unease took a toll on him, as he was so distressed that after one recording session, he even vomited.

In the subsequent years, Tony Bennett’s life took a tumultuous turn. He went through a divorce with his first wife, and during this period, he fell into the grip of a cocaine addiction. Additionally, his venture into running an independent record label proved unsuccessful, leading to financial struggles.

His personal life also suffered as he entered into an unhappy second marriage with Sandra Grant. The combination of his failed business endeavors, drug addiction, and marital issues plunged him into a deep state of debt and despair.

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Reflecting on this difficult period, Bennett candidly shared with the New York Times in 1999, “I had an ax over my head. I was spending more than I was making, on advertising, publicity, and all.”