Music and blurred chatter made up the din of the restaurant one night in New York. Like any broken-hearted male, Frank Sinatra sat at the bar at Toots Shor’s Restaurant with pal Jackie Gleason at his side, hoping for eventual healing. What helps a man get over a woman for the evening? A serious drink would be the solution. The strongest and most loyal relationship between Frank and Jack Daniels had begun, lasting longer than any other woman who would enter his life. A tumbler of Daniels, three ice cubes and water became a signature facet of the look, along with tailored suits and a fedora.
Sinatra was a man of distinction on the outside and a private life of childhood abuse, broken hearts, anger and Mafia connections on the inside. He was the patron saint of the lovely disasters and the strangers in the night: the losers, the lust-driven, the gamblers, the drinkers. Whatever you claimed to be, chances were he already took a hit for it.
Joy, pain, anguish, desire—it was all heard in his singing voice. His life resume had the work experience of love and loss, yet he delivered promises in his craft. There was hope. There was something for the beautiful losers out there. If we can make it there, we can make it anywhere.
This past weekend would have been Ol’ Blue Eyes’ 100th birthday. So pour yourself two fingers of Jack and raise a glass to the man.
This piece also appears on lyndseydee.com
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