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Frank Sinatra: The Stories Behind His Songs

| December 12, 2016 | 7 Comments

When Francis Albert Sinatra was born on December 12, 1915, the world was given the greatest friend a song and songwriter would ever know.

Starting out as a saloon singer in musty little dives (he carried his own P.A. system), he eventually got work as a band singer, first with The Hoboken Four then with Harry James, then Tommy Dorsey. In 1942 he started his solo career, instantly finding fame as the king of the bobbysoxers, becoming the most popular singer of the era among teenage music fans.

With “Sinatra-Mania” in full swing, Frank scored a phenomenal 23 Top 10 singles between 1940 and early 1943 alone, and was nicknamed “The Voice” by his fans.

To celebrate Ol’ Blue Eyes’ birthday today, Performing Songwriter takes a look at five songs he made famous, and the writers behind them.

“Nice ‘n’ Easy” – Lyrics by Alan & Marilyn Bergman, Music by Lew Spence

Marilyn Bergman told Performing Songwriter: “With ‘Nice ‘n’ Easy,’ a call had gone out, a kind of open casting call, that the Sinatra people were looking for a song for Sinatra, a title song for an album of lightly swinging love songs. Every writer in Hollywood submitted something and luckily we got the call. Writing for Frank Sinatra was like writing for a character in a play. You know exactly the language, the look, the attitude, everything.”


“My Way” – Lyrics by Paul Anka, Music by Claude François and Jacques Revaux

Paul Anka told Performing Songwriter: “I lived in France, spoke French, knew a lot of French artists. I heard this song on the radio called ‘Comme D’Habitude.’ The song was co-published by a guy I’d put in business. The original lyric was about a husband and wife, bad marriage—’We get up in the morning and as usual, I look at your armpit … ‘ Very French, you know (laughs). It wasn’t a big hit. But I heard it another way. It kept gnawing at me. I asked the publisher for the rights. We weren’t buying the pyramids. It was a two-page agreement, and that was it. I came back to the States with it and put it away.

“Don Costa, who was my A&R director my whole life, had introduced me to Sinatra. Fade in, fade out. It’s 1968, I’m in Florida performing. Sinatra’s there shooting a movie. He calls. He comes to my show. We have dinner. He says, ‘I’m doing one more album, then quitting the business.’ He had always teased me about writing songs for him. But in the years that I knew him, he hated pop music. Hated Presley, hated rock. Wouldn’t sing it, until Don convinced him. Then he started to do more contemporary stuff.

“I went home to New York City and realized, ‘Frank is retiring. I want to write something.’ So I took the French record out and transposed it to the piano to get the feel and vibe. It started to mold into this different song. I sat at the typewriter. It was 1:00 in the morning, a storm outside, and I thought, ‘What would Frank say if he was writing this?’ I thought metaphorically. ‘And now the end is near … ‘ The song started to write itself. I used dialogue that I would’ve never normally used for a song, but it fit what he was about and what he would say. ‘Chewed it up and spit it out‘ and all that stuff. For the next four or five hours, I worked on it and completed it.

“I called them out in Vegas and said, ‘Guys, I’ve got something for the album.’ We all knew it was something special. Three months later, Frank called me from United Studios and put the phone to the speaker and played it for me for the first time. I started to cry. I’d never had a creative moment like that.”


“It Was A Very Good Year” – Words and music by Ervin Drake

Ervin Drake told Performing Songwriter: “One evening in 1961, I was walking through 1650 Broadway, which was then the other Tin Pan Alley. The main one was 1619, the Brill Building, the legendary one. But there was an awful lot of action in 1650. Irving Berlin had his offices there.

“I was walking down a hall, passing a publisher’s office—a fellow who was a friend of mine. As I’m walking past, the door opens and it’s my friend, Artie Mogul. He said, ‘Erv, you’re just the man I wanted to see.’ I said, ‘What about?’ He said, ‘You know I’m in the business with the Kingston Trio. Have you got a song for them?’ I said, ‘You mean, neo-folk?’ He said, ‘Yeah, right, you know, the kind of stuff they do.’ I said, ‘Well, no, I don’t actually. But let me go to your piano room.’ And I went inside and I dug inside my coat and I pulled out a diary. And I looked in the back where I have ideas for songs, and I very, very nervously ran down the whole list of things, discarding, discarding … well wait a minute here’s one: ‘Story of a guy’s life told in wine vintage terms. Neo-folk, possible title, “It Was a Very Good Year,” to express the vintage part of it.’ And with that I sat at the piano and very, very swiftly wrote the song. Then I played it for Bobby Shane [of the Kingston Trio] the next day and they ended up recording it.

“Now, years go by, and in 1965 we hadn’t had a vacation in some time, so I elected to take my late wife and kids and head for London. And I thought, ‘I’ll call a friend of mine.’ His firm in London handled another song of mine, ‘I Believe.’ And he said ‘How do you like your new Sinatra recording?’ I said, ‘He did “I Believe”?’ He said, ‘No, no, no. “It Was a Very Good Year.” I’ll play it for you over the phone.’ And he plays this marvelous recording.

“I couldn’t wait. When we got home, the first thing I did was head for the record store and buy that most superior recording. I loved the way Sinatra phrased it.

“Years later I got to know Frank really well. One night we were sitting together out in Vegas at the Sands and I said to him, ‘By the way, for whatever reason, it never occurred to you to sing the middle part that I wrote?’ He said, ‘What middle part?’ I said ‘The Elizabethan nonsense syllables, they went “Hi-lura-lie hi-lura-lura-lie.’” He said, ‘Buddy, you are so lucky I didn’t do it.’ I said ‘Why?’ He said, ‘Cause with me it would have come out “Hi-shooby-doo, hi-shooby-scooby doo.” (Laughs)


“All the Way” Lyrics by Sammy Cahn, Music by Jimmy Van Heusen

Sammy Cahn told Paul Zollo in Performing Songwriter: “A melody will never be out of fashion. Sinatra recorded 87 of my songs. Some three times. And the amazing popularity of this man … how many people in the world living now do you think made love to the sound of Sinatra? So when people go to see this man, he represents something beyond words and music. It’s a presence. When he sings, [sings] ‘It’s such a lovely day,’ he makes the word ‘lovely’ sound lovely. Ninety-nine singers out of 100 wouldn’t sing it that way. [Sings] ‘When somebody loves you, it’s no good unless he loves you … ‘ The word ‘love.’ He gives the words their full meaning. And that’s why he’s Sinatra.”


“The Best is Yet To Come” – Music by Cy Coleman, Lyrics by Carolyn Leigh

Though “The Best Is Yet to Come” was actually written for and introduced by Tony Bennett, it was Frank Sinatra who recorded on his 1964 album It Might As Well Be Swing, and made it popular. It was actually the last song Sinatra sang in public, on February 25, 1995, and the words ‘The Best Is Yet to Come’ are imprinted on his tombstone.

Category: In Case You Haven't Heard

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  1. Cure Songwriter’s Block and Get Inspired | David Das | December 12, 2011
  1. Donald Schully says:

    Mr Sinatra’s phrasing and personal touches is untouched by others. Watch HIGH SOCIETY, his duet with Bing Crosby, “Well Did You Ever” is one pf my favorites. PAL JOEY is one of his best movies

  2. ROBERT SELJAN says:


  3. Stuart Troutman says:

    Is there a www site for a question regarding slightly alternate lyrics to sinatra’s rendition(s) of “Luck Be a Lady”?

  4. Les Block says:

    “The Best is Yet To Come” was originally written for Sinatra but for some reason he didn’t record it at the time. It was only after Tony Bennett recorded it that Sinatra recorded his version for which he slowed down the tempo. Bennett once told me that he was told by a Sinatra music director that when Sinatra was looking for songs to record, he would check out what Bennett had recorded because “Tony picked out great songs.” Certainly that is the case with “The Best Is Yet To come.”

  5. Sinatra was truly one of a kind, no one can compare before or since. He really STUDIED his music, decided what phasing he wanted and when to take a breath. A true professional. I am a former professional musician and elderly now, but I can tell you NO one does it better than Frank Sinatra. That’s why his music is so enduring.

  6. Russell Satterthwait says:

    If Sinatra was the greatest friend a song ever had, one primary reason is the respect he had for the creativity and struggle of the songwriter. Unconsciously or not, Sinatra,s approach to a song demonstrated Mozart’s dictum: beauty with simplicity. Reams of descriptive terms have been justifiably showered upon Mr. Sinatra regarding his diction, subtle emotional delivery and phrasing,etc; all of which are on the mark and the logical outcome of this creative process is in a few words: vocal authority. Hopefully, the lessons which he has imparted will be studied for years to come by aspiring singers.

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