These are a few of Frank Sinatra’s greatest songs, ranging from the early 1940s to the late 80s. His music covers an extremely wide spectrum: jazzy big band-driven to simple piano accompaniment, from upbeat swinging, joyful, confident to sad, regretful and tired.

Of course, there are so so many songs to choose from. Depending on your age, and how familiar you are with Sinatra’s music, some of your choices for Sinatra’s greatest songs may coincide with mine and some may emphatically not. Some of you will focus on the 1940s, many more on the 50s, while others mainly know the mature sound of “My Way” and “New York, New York.”

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