The Most Famous Frank Sinatra Songs In Jazz History

As part of our journey through the best jazz songs of all time, we take a look at some of the most famous Frank Sinatra songs which make up the discography of ‘Ol Blue Eyes.

It is irrefutable that Frank Sinatra was one of the greatest singers of the twentieth century. He covered many different styles in a career that spanned sixty years and is reported to have sold 150 million records worldwide.

Born Francis Albert Sinatra in Hoboken, New Jersey on 12 December 1915. He developed an interest in music, and especially big band jazz at an early age, and was greatly influenced by the singing of Bing Crosby.

In addition to his singing career, Sinatra was also in demand as an actor, which would take off significantly in the 1950s. He was also politically active which was something that would remain an important part of who he was throughout his life.

Sinatra’s first successes in the music industry were with the big bands of Harry James and Tommy Dorsey and following this signed with Columbia Records in 1943.

Releasing his debut album three years later, The Voice Of Frank Sinatra the singer found immediate acclaim and commercial success becoming the idol of the adolescent female fans known as bobby soxers. The album would reach No1 on the Billboard album chart.

After several successful recordings for Columbia, including a Christmas album, Sinatra signed with Captial Records and over the next five years recorded what would be regarded as some of the first ‘concept’ albums.

Leaving Capitol in 1960, the singer started his own label Reprise Records which released a string of highly acclaimed jazz albums, including the Sinatra At The Sands live recording from the Vegas club and with Count Basie and his Orchestra in 1965 and a year later, Francis Albert Sinatra & Antônio Carlos Jobim.

Just a few years later in 1971, Sinatra retired, although this would turn out to be short-lived, and in 1973 he was back performing and recording again.

Frank Sinatra would continue to perform throughout the remainder of the decade, often at high profile venues in New York with Ella Fitzgerald and Count Basie, and again with Basie and Sarah Vaughan at the London Palladium. He would also return to Las Vagas playing at Caesars Palace.

In 1979 Sinatra was again back in the studios with the resulting album, Trilogy: Past Present Future being released the following year.

An ambitious three LP set, each individual album was conceived as a moment in time. On The Past Sinatra would perform standards for the first time since the early sixties, and The Presentfocussed on pop hits.

The third LP was the strangest of all, a set of all original songs written and arranged by Gordon Jenkins that were derided at the time of release as rather directionless and not able to sit comfortably as fully realised concept.

While Sinatra would continue to perform and record until 1995 when ill health would force him to finally retire, his best work can be said to be in his heyday of the 1950s until his first retirement in 1971.

So, without further ado, here are some of the most famous Sinatra songs ever…

Someone To Watch Over Me (1946)

From the album The Voice of Frank Sinatra recorded in 1945 and released the year after, at the time it was regarded as an early concept album with all the songs having a common theme, mood or instrumentation.

Arranged and conducted by Axel Stordahl, ‘Someone to Watch Over Me’ written by George and Ira Gershwin is a song that Sinatra would return to frequently throughout his career and has a wonderfully serene arrangement for Sinatra baritone voice, here at his prime, and at the beginning of an illustrious career.

I Get A Kick Out Of You (1954)

Another tune that Sinatra seems to have made his own, ‘I Get A Kick Out Of You’ was written by Cole Porter and on this outing gets a gentle swing feeling, with Sinatra in full control of his vocal and the song.

Recorded for one the singers most acclaimed album of the time, Songs For Young Lovers, the sessions took place in November 1953 with the album hitting the shops in 1954.

The song was arranged by George Siravo who would arrange much of Sinatra’s material featured in his night club performances.  This version is of note due to Sinatra’s exceptional interpretation of the lyrics, and the subtle changes in mood and tempo in the arrangement.

I’ve Got You Under My Skin (1956)

This time out, for his fourth album for Capital Records, the arranging duties were given to Nelson Riddle who gives the music a more ebullient and carefree feel.

The album concept for Songs for Swingin’ Lovers! is clearly felt in the gently swinging arrangements that only has one ballad feature for the singer.

A brave move, but one that works well in this context, is Riddle’s desire to give ‘I Got You Under My Skin’ a more optimistic mood and feel, despite the rather melancholy story depicted in the lyrics.

Come Fly With Me (1958)

Sinatra continues his remarkable run of albums of the mid to late fifties with Come Fly With Me recorded in October 1957.

This time out conducting, and arrangements were handed over to Billy May and the music has a lightness of touch that is quite different from that of Nelson Riddle.

The title track of the album was written at Sinatra’s request by Sammy Cahn and Jimmy Van Heusen and was a big hit for the singer, as was the album that reached No 1 in the Billboard album charts where it remained for five weeks.

Intended to depict a trip around the world, the song has a carefree air about it, and has been a perennial favourite of singers the globe over.

Embraceable You (1960)

Conceived as an album of ballads, with the exception of the title track Nice ‘n’ Easy, th is was another hugely successful album for Sinatra.

The arrangements are again handled by Nelson Riddle, although one gets the feeling that they are a little saccharine. Despite this, Sinatra is majestic and his vocal on each is a joy and model of control.

Written by George and Ira Gershwin, ‘Embraceable You’ has always proved popular, and again would remain in Sinatra’s book for many years to follow.

We’ll Meet Again (1962)

In perhaps a surprising move, Sinatra records in London towards the end of a tour raising money for children’s charities and chose to record a selection of British material.

The resulting album Sinatra Sings Great Songs from Great Britain was released in the UK in 1962, but not available in the US until the early nineties.

The arrangements were written by Robert Farnon, and the album was recorded over three evening sessions.

Tired from the tour, Sinatra was apparently not feeling his best and not happy with his performances, but a cursory listen suggests otherwise. Farnon’s arrangements are superb, supporting the song and eschewing over sentimentality.

A clever choice of song, ‘We’ll Meet Again’ was of course made famous by Vera Lynn when she recorded in 1939.

Fly Me To The Moon (In Other Words) (1964)

A second studio collaboration between Sinatra and Count Basie in 1964 resulted in the album It Might As Well Be Swing featuring ten classic songs arranged by Quincy Jones.

The album cannot do anything but swing with Basie and his Orchestra involved, and ‘Fly Me To The Moon’, originally titled ‘In Other Words’ by composer Bart Howard.

Originally written by Howard in ¾ time but Quincy Jones heard it in 4/4 for this arrangement for Sinatra. He heard it right and the song has been popular for the singer ever since.

My Way (1969)

This is the song that is indelibly linked to Sinatra, and the singer’s version first appeared on his album of the same name that featured contemporary popular songs by Simon and Garfunkel, and Lennon and McCartney.

Based on a song by Jacques Revaux with lyrics by Gilles Thibaut and Claude François, titled ‘Comme d’habitude’ and reached No 1 in the French pop chart in February 1968.

Singer-songwriter, Paul Anka heard the French version of the song and obtained consent to rights to adapt and publish the song with new lyrics, as long as the original composers of the melody retained their share of any royalties.

Anka made some changes to the harmonic and melodic structure of the song and rewrote the lyrics with Sinatra in mind. When it came to recording the song, Sinatra got it one take.

Thanks for reading! 

Looking for more jazz classics? Check out our picks of the best jazz albums of all time.

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