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His career took off when he became the featured vocalist with first Harry James, with whom he recorded “All or Nothing at All,” and then Tommy Dorsey. In 1942 he began his solo career and was greeted by swooning bobbysoxers. His natural acting ability became apparent in 1945’s Anchors Aweigh, in which he also sang “I Fall in Love Too Easily” and danced (with Gene Kelly, no less).

His health and personal life took a hit in the early ‘50s when he left his wife for Ava Gardner, suffered a hemorrhage of his vocal chords, and was dropped by his agent and studios. He staged a comeback in From Here to Eternity (1952), winning the Academy’s Best Supporting Actor Award. He continued his acting career—both dramatic roles and musicals—as well as nightclub appearances and recordings. His sides with Nelson Riddle were hugely successful, and “Ol’ Blue Eyes” developed an emotional maturity best illustrated in The September of My Years (1965).

The number of songs that he introduced or that were written for him would entail pages, for instance “Polka Dots and Moonbeams” (1940), “Saturday Night Is the Loneliest Night of the Week” (1944) and “My One and Only Love.” Just a few of the Sammy Cahn songs include “Come Fly with Me” and “All the Way” (1957), “Only the Lonely” (1958), and “My Kind of Town” (1964).

Sinatra was honored in many ways for his accomplishments and his humanitarianism, culminating with a Congressional Gold Medal in 1997.

- Sandra Burlingame