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The 14 Top Frank Sinatra Songs Of All Time

There is no doubt about the pedigree of Frank Sinatra. He is one of the biggest selling artists of the 20th Century. His repertoire crossed genres, at times with ease, and he has made some songs “his own.”

It wasn’t all plain sailing for Ol’ Blue Eyes, though. There were times when he was out of favor. And there were times when his personal life was called into question. But, he seemed to be able to survive most of it and still come back.

What Was He?


Some jazz musicians regard him as a jazz singer. The reason for that is a lot of his repertoire were songs from theater productions and show tunes. That makes up quite a high percentage of what we call jazz standards.

He also worked with several jazz greats, Duke Ellington and Count Basie, to name just two. He had a style that seemed to fit the music. But was he really a jazz singer? Or was he a singer who took jazz songs and sang them in his own style?

All of the above?

Listening to the top Frank Sinatra songs of all time, I would say he was not a purist jazz singer. Ella Fitzgerald, Sarah Vaughn, Billie Holiday, and Mel Torme were. Even Louis Armstrong. 

Frank seemed like a singer, albeit a very good one, who sang some jazz, but not as the jazz singers do. Some of the most well known Sinatra songs could hardly be called Jazz, more like Pop songs.

Concept albums

Strange as it may sound, he was one of the first to record concept albums that told a story. In the Wee Small Hours was one in 1955, and Watertown is another. And, of course, Come Fly With Me, among others. The people around him were innovative, if nothing else.

Who Was Frank Sinatra? 

He was born in New Jersey in 1915 to an Italian immigrant family. He grew up in the Big Band era and was particularly respectful of the greats of the time and admired Bing Crosby.

It was the time of Swing, and the Big Bands usually had a featured vocalist. Sinatra got in on the act and worked with Harry James and Tommy Dorsey early on in his career. He had a film career that was rather up and down at times. “From Here To Eternity” is a particular high point.

But, what wasn’t up and down was his residency in Las Vegas. From there, he worked with Count Basie, amongst others. Sinatra at the Sands was one recorded work from this time in Vegas in 1966.

Not A History 

This is not going to be a history of the man, so I will be brief. We are here to consider his music. However, a little background and opinion is not a bad thing to fuel some discussion. So let’s make a start. And, I will begin where many others might finish.

The 14 Top Frank Sinatra Songs Of All Time

My Way

Probably the most instantly recognized Sinatra song of all, and it is certainly not Jazz. Nevertheless, it is the song that has made the most worldwide impact. Released in 1969 and included on his album of the same name, it was a huge success.

It reached #5 in the UK, where it stayed in the Top 40 for nearly 18 months. It peaked at #27 in America.

A French Song

“My Way” was written by Claude Francois and Jacques Revaux. It was originally known as “Comme d’habitude” or “As Usual” in English. It did reasonably well and stayed at the top of the French chart for one week in 1968.

Paul Anka heard the song and reworked a new set of lyrics to the melody. The storyline now became different and was a defiant look back at how life was lived. 

It has been covered by plenty of people, including Elvis Presley. But, none quite capture the feeling Sinatra finds in his performance.

An Unusual Popularity

Besides being the song it is, it has also found unusual popularity. It seems that it is a very popular track that is played at funerals and memorial services.

High Hopes

Sinatra released this song in 1959, and it was included in the film “A Hole In The Head.” It was also included on an album released two years later called, All The Way.

The song was written by lyricist Sammy Cahn and Jimmy Van Heusen. It is a song that is fondly thought of because of its lyrical content. It talks about animals and insects doing seemingly incredible acts.

An ant moving a rubber tree plant, and a ram making a hole in a huge dam. Described by Cahn’s lyrics as being “high apple pie in the sky hopes.” The meaning is simply that we can do anything if we try.

The Impact Of The Film

There is little doubt that the film helped the song to become popular and increase Sinatra’s already growing reputation.

I’ve Got The World On A String 

It’s not uncommon for today’s artists and producers to look back in time to find some songs. There might be several reasons they do this. It isn’t just because there isn’t any good new material. The nostalgia factor can play a big part in the success of a recording.

This is not a new phenomenon, and artists and musicians have always looked back to the generation that preceded them for some good material. “I’ve Got The World On A String” is a good example of that.

The song was written by Harold Arlen and Ted Koehler in 1932, and Sinatra’s team revamped it for a release in 1956. Sinatra delivers a typical ‘colla voce’ beginning, but then the big band kicks into action.

One For My Baby (And One More For The Road)

Sinatra was not averse to promoting his “bad boy” image, and this song does just that. It is described by some as a “booze-soaked” classic. It is taken from the musical film “The Sky’s the Limit” from 1943. The music was written by Harold Arlen, but it is the lyrics of Johnny Mercer that tell the story.

Some say it has something to do with Mercer’s unfortunate affair with a very young Judy Garland. The story is about a man in a bar talking about his romantic problems while requesting more drinks from Joe, a bartender.

Sinatra must have liked this song because he recorded it four different times in different ways.

Love And Marriage

Some of the top Frank Sinatra songs of all time we have looked at so far you may not be so familiar with. This one, however, I should imagine is a Frank Sinatra song everybody knows

This is another song written by the irrepressible Sammy Cahn and Jimmy Van Heusen. It was included on the album, This Is Sinatra! There were plenty of cover versions. Perhaps the most notable ones are by Bing Crosby and by Peggy Lee.

It was recorded twice by Sinatra, with both arrangements made by Nelson Riddle. There are some subtle but noticeable differences between the two versions. A very happy song with Sinatra in a good voice.

The Best Is Yet To Come 

This is a song with a certain amount of irony attached to it. It was written in 1959 by Carolyn Leigh, who wrote the words, and Cy Coleman, who composed the music. 

Sinatra recorded it with the Count Basie Orchestra and Quincy Jones, and it was released in 1964. It was included on his album, It Might As Well Be Swing. His daughter, Nancy, did her version in 1963 on her album, Yesterday’s Love Songs, Today’s Blues.

A Final Performance

His last public performance was at the grand old age of 80 in Palm Strings. The voice may have started to disappear a little a few years before. But, the charisma was still there. This was Sinatra, after all.

The last song of that last show was “The Best is Yet to Come.” That is what was chosen to be engraved on his gravestone in California.

The Good Life

A song that I can remember as a kid. It was released in 1964 and taken from his album, It Might As Well Be Swing, with Count Basie.

This is another collaboration with Basie that proved a good move for Sinatra. Working with him took the recordings and the quality of the songs up another level. It may be better known and associated with Tony Bennett than Sinatra. Nevertheless, his version was typical of easy-going Frank. 

The song was originally French and called “La Belle Vie.” It was written by Sacha Distel with French lyrics by Jean Broussoll and English lyrics and translation by Jack Reardon. One of my favorite Frank Sinatra songs.

I’ve Got You Under My Skin

Sinatra’s early success had begun to wane in the early 50s. Personal problems didn’t help, but things looked up when he signed with Capitol in 1953. His last few records had been rather second-rate in terms of the quality of the songs. Pairing up with Nelson Riddle solved that problem.

“I’ve Got You Under My Skin,” written by Cole Porter, brought out the “crooner” in Sinatra. It was taken from the album Songs For Swingin’ Lovers! It was one of the albums that revived his career at this point. Also helped along by the film “From Here To Eternity.”

The 50s may have started rather badly for Sinatra, but things were now looking up.

Come Fly With Me

I mentioned earlier that Sinatra has experimented with the idea of a concept album. This is an example. It wasn’t a deep commentary on anything, in particular, just a trip around the world. But, the basis was there. 

The songs had a geographical theme and were named after different places. The album bore the same name, Come Fly With Me.

The lead song, written by Cahn and Van Heusen, encapsulates the easy-going style that Sinatra was famous for. It was released in1958 and became a favorite of Sinatra fans.

It Was A Very Good Year

The year 1965 turned out to be a very successful one for Sinatra, as his style changed in an attempt to increase his popularity. This was one of the songs that made a big impact. It was taken from his album, September of My Years.

The song was written by Ervin Drake and was a nostalgic look back on his life and the girls he had known at various times. It is full of a melancholy feeling which is both happy in its memories of those days.

He remarks that he is older now and can appreciate them all for what they were to him. The arrangement places it in a minor key that creates the atmosphere. Sinatra’s vocal excels and adds poignancy to the track. It reached #28 in the American chart.

Strangers In The Night

Sinatra began to change his style with this 1966 release. He attempted to create a more contemporary Pop sound. That is what was happening in music at this time. It paid off for him. 

Taken from his album of the same name, it was the last time he worked with Nelson Riddle. The album attempted to combine new material with standards and show tunes. The album and single were a success, and the album became his last successful recording.

It was written by Bert Kaempfert, Eddie Snyder, and Charles Singleton. Sinatra was not known as a singer who could improvise like some jazz singers, Ella Fitzgerald or Mel Torme. However, he did include a few low-key “doo bee doo bee doo’s” at the end.

That’s Life

Another song that Sinatra made famous. It was released in 1966 when the charts were dominated by Pop and developing Rock music. But, he still managed to get a chart position. It reached #44 in the UK and #4 in America.

It could be a little autobiographical… 

He took a few knocks in his career and had to stand up and fight back on many occasions. That is what this song is all about. He is saying, “That’s Life” deal with it.

It was composed by Kelly Gordon and Dean Kay and was first recorded by Marian Montgomery in 1963, but it wasn’t a success.

It was interesting that it included some Soul female backing vocals, not something Sinatra employed often. But, it made the track something special and contributed to its success. Another song that was often included in his stage shows.

Fly Me To The Moon

This, for me, was always one of Frank Sinatra’s greatest songs. It has a style and feel to it that is simply Sinatra. 

By the time Sinatra recorded it… 

There had been plenty of versions. Sinatra’s version came out on the album, It Might As Well Be Swing in 1964, a collaboration with The Count Basie Orchestra.

It was written by Bart Howard a decade earlier and was originally called “In Other Words.” When he wrote it, he thought it would make a good waltz. Quincy Jones rearranged it to make it a 4/4 Swing song. He got that right.

It has become one of the definitive Sinatra songs and will be forever linked with him despite the cover versions. It remained part of his stage act for decades.

New York, New York

And so, we come to the last of my selections for the top Frank Sinatra songs of all time. He was born in Hoboken, part of the metropolitan area of New York City. So, this song is a tribute to New York, where he grew up and got his chance.

It was originally written for Liza Minnelli for the film of the same name directed by Martin Scorsese. But, it will be forever associated with Sinatra and was his last big single. It was included on his album from 1977, Trilogy: Past, Present, & Future.

“New York, New York” was released twice, in 1980 and 1986. It was the latter where the song was most successful, reaching #4 in the UK and #32 in America.

Start spreading the news…

It is a song that says you are proud to be a New Yorker. It has a certain style and elegance, and he sings it with great passion. “If I can make it there – I’ll make it anywhere.” In my view, his best song and one that screams “Sinatra” at you.

Looking for More Great Music?

We can help with that. Take a look at our detailed articles on the Best Dean Martin Songs of All Time, the Best Louis Armstrong Songs of All Time, the Best Songs Of All Time, and the Best Jazz Songs for more incredible song selections.

Of course, you’ll need to listen to the songs. So, check out our in-depth reviews of the Most Comfortable Earbuds, the Best Sound Quality Earbuds, the Best Bass Earbuds, the Best Noise Isolating Earbuds, and the Best iPhone Earbuds you can buy in 2023.

Plus, don’t miss our comprehensive reviews of the Best Headphones for Music, the Best Headphones Under $200, the Best Wireless Bluetooth Headphones, and the Best Bluetooth Headphones for Commuting currently on the market.

Top Frank Sinatra Songs Of All Time – Conclusion

Any performer who sells more than 150 million records has got to be something special, and so he was. As I said earlier, he wasn’t always the flavor of the month. There are a lot of people that don’t like his style of music.

But, you can’t deny that he survived just about every change in music and some controversies in his private life.

The thing about Sinatra was that he was more than just a singer or a performer. He was an artist. They don’t come along very often. Even in his 70s, the years had taken their toll a bit, but it was just enough to say that you “went to see Sinatra.”

Of course, he had some help along the way… 

He worked with some great bands in his early days and, of course, later. The influence of Count Basie and Nelson Riddle can’t be underestimated.

And, of course, he had great songs. But, all his material was also recorded by others in his peer group. Even the Rock and Pop artists and bands who came later paid their respects. 

Working with his daughter, Nancy, later on also provided an extra dimension to his style, and together they produced some good songs. But, you would probably expect that. Love his music or not, he was unique. I am not sure we will see the likes of him again.

Until next time, happy listening.

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About Jennifer Bell

Jennifer is a freelance writer from Montana. She holds a BA in Creative Writing and English, as well as an Associate of Applied Science in Computer Games and Simulation Design.

Her passions include guitar, bass, ukulele, and piano, as well as a range of classical instruments she has been playing since at school. She also enjoys reading fantasy and sci-fi novels, yoga, eating well, and spending time with her two cats, Rocky and Jasper.

Jennifer enjoys writing articles on all types of musical instruments and is always extending her understanding and appreciation of music. She also writes science fiction and fantasy short stories for various websites and hopes to get her first book published in the very near future.

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