The Hidden Meanings Behind Popular Frank Sinatra Songs  

Mike Rothschild
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While the vast majority of the songs Frank Sinatra recorded were love songs, either odes to its loss or tributes to its greatness, he also recorded a number of songs about places and people that were meaningful to him. Hidden behind those songs are stories about how they came to be and how they got to Sinatra. Hidden song meanings are always interesting, sometimes scandalous, and Sinatra's vast catalog is full of backstory.

Some are cuts he loved, some others he hated and only performed because they were expected of him. Many are songs he recorded numerous different times in various contexts - from swing to torch songs to disco (!). Here are the stories behind some signature Sinatra songs, including a few you might never have heard.

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Songwriter Paul Anka based the melody for “My Way” on the French pop song “Comme D’Habitude” which he’d heard and bought the rights to. He then wrote lyrics tailored for Sinatra based on the news that the singer was retiring in 1968. The song was released in early 1969 and became a massive hit that was covered by numerous artists.

One of these, ironically, was Elvis Presley, whose music Sinatra detested – and who took the song higher on the charts than Sinatra did. Sinatra himself became sour about his signature song, finding it bombastic, arrogant, and “torturous” to sing. see more on My Way
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A track Sinatra recorded four separate times, it’s easy to assume this was written either about or for his daughter Nancy. It wasn’t, instead being penned in 1942 by Jimmy Van Heusen and Phil Silvers about fellow songwriter Johnny Burke’s wife Bessie, and meant to be sung to her as a goof. It became so popular that the duo began performing it at other women’s birthday parties, changing the name from “Bessie” to whoever was the birthday girl.

When they performed it at Nancy Sinatra’s birthday in 1944, they changed it to Nancy, and Frank burst into tears thinking they’d written the song for her. They wisely agreed that they had, and Sinatra made the song part of his regular repertoire.
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Sinatra cut “Night and Day” five different times, making it his most recorded song. The track was originally written by Cole Porter in 1932, and became so associated with the songwriter that the autobiographical film about him from 1946 was called Night and Day.

Sinatra cut it during his first solo session in 1942, and would come back to it about once a decade – including an ill-advised disco version, released as a single in 1977.
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One of Sinatra’s signature early '60s songs, “It Was a Very Good Year” finds the singer looking back on his life and comparing various phases of it to wine vintages. But while the song sounds like it was tailor made for Sinatra, it was actually written by Ervin Drake for Jamaican folkers the Kingston Trio to record.

Sinatra recorded his version several years later – and omitted a middle passage of Elizabethan-style nonsense syllables.

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