As Gay Talase suggested in his famous Esquire profile, at the height of his career, the state of Frank Sinatra’s health had the potential to cause ripples throughout the music industry. But as the decades rolled on and his Rat Pack accomplices died one by one, Sinatra’s career wound down, and his growing list of maladies, illnesses, and medical emergencies became his full-time occupation.
His last concert took place on February 25, 1995, at the Palm Desert Marriott Ballroom in Palm Desert, California. After this, he made a handful of public appearances, most notably to be awarded the Congressional Gold Medal in April 1997. But behind closed doors the acclaimed vocalist was dealing with a growing list of illnesses, including a bout of pneumonia that hospitalized him in 1996, bladder cancer, heart and lung issues, and high blood pressure, per Spencer Leigh’s “Frank Sinatra: An Extraordinary Life.”
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Sinatra was reportedly increasingly paranoid and anxious in his later years. In 2017, his former manager, Eliot Weisman, told Fox News that the man he referred to as “The Boss” had also begun to abuse an antidepressant medication called Elavil. The drug, Eliot said, led to the singer’s cognitive decline in his later years — and accelerated his retreat from public life.
