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.”

          I don’t have a favourite or greatest Sinatra song, but these are some of the ones I have liked a lot for a long time in no particular order. His songs have accompanied me throughout most of my life. I fell in love with Frank Sinatra’s voice and style when I was 14 years old. I fell hard. I was obsessed. 50 years later, I still never get tired of listening to his inventive and skillful variety of music. Have fun reading about and listening to my choices. Let me know in the comments what you think his greatest songs are and why.

1. Five Minutes More From just after World War II, so Sinatra’s voice is lighter, but so smooth.

2. Lean Baby I love the humour in the lyrics. Also, it is clear that he is having fun singing it.

3. Too Marvelous for Words Charming, clever poetry and Sinatra knew it and highlighted it.

4. It Had to Be You So romantic. This is from the Trilogy album recorded in the mid-70s.

5. A Foggy Day Maybe because its setting is London, maybe because his thrill at meeting her is so clear . . .

Throughout my career, if I have done anything, I have paid attention to every note and every word I sing – if I respect the song. If I cannot project this to a listener, I fail.

6. Violets for Your Furs So elegant and evocative of gentlemanly courtesy and romance.

7. Summer Wind I think of wide, warm golden beaches with Sinatra’s voice wafting over the landscape.

8. The Girl from Ipanema I love the yearning in his voice and the lyricism.

9. Mack the Knife The jazz feeling and his mentions of the great singers who performed the song before him and the amazingly skilled musicians in the studio with him that day make me smile. Throughout his career, he acknowledged the team effort: arrangers, songwriters, conductors.

10. The Best is Yet to Come The confidence and the warmth in his voice is so seductive.

11. Something’s Gotta Give Sexy, and I love how his Hoboken accent never detracted from the clearness of his phrasing.

12. I’ve Got You Under my Skin For me, and for many Sinatra fans, this is the best and most exciting combination of singer, arrangement and song.

Do you agree with my choices? Do they bring back any memories?

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