Few artists bridge the gap between and the wider public like ‘Ol’ Blue Eyes’. Here we take a look at 20 of the greatest from across his iconic career.
is one of the biggest selling artists of the 20th Century, with numerous hits that are instantly recognisable to almost everyone.
At the same time, many musicians regard him as an authoritative interpreter of the Great American Songbook, show tunes and theatre songs that makes up a significant proportion of the standard repertoire.
(as he was affectionately known) also collaborated with a number of important musicians, including and Duke Ellington, in an illustrious career that saw him lauded as one of the greatest singers of all time, as well as an -winning actor and era-defining style icon.
In this article we’ll take a look at twenty of Sinatra’s most iconic recordings, ranging from snappy swingers to moving torch songs and everything in between.
And, for those of you looking for a first taste (or a classic re-listen) our top pick from the discography is without a doubt Live at The Sands which you can find on Spotify, Youtube or your favourite record store.
20. I’ll Never Smile Again
was born in 1915, to Italian immigrant parents in Hoboken, New Jersey. As a teenager, he became a fan of , idolising as he started to work professionally as a singer himself.
During the swing era, star bandleaders led hugely popular big bands that would often include a featured vocalist. Sinatra first found some success filling this role with trumpeter Harry James’ band, before moving on to front ‘s orchestra.
He had a number of huge hits with Dorsey, among them this mournful ballad, on which Sinatra is backed by vocal group the Pied Pipers and a distinctive celeste part. ‘I’ll Never Smile Again’ was written by Ruth Lowe as she grieved following the premature death of her husband.
Sinatra – at this point a skinny young man with a charming smile and piercing blue eyes – became a massive heartthrob during this period, as hordes of teenage girls (known as “bobby soxers”) flocked to his concerts.
This particular recording spent 12 weeks on top of the Billboard charts.
19. is Coming to Town
No singer worth their salt in the middle of the 20th century could miss the chance to put out an album of Christmas classics.
There’s plenty to choose from in this corner of the Sinatra discography (Jingle Bells, Have Yourself a …) but our favourite is his feel-good mid-tempo version of is Coming to Town.
Released in 1948 on , it was written by J. Fred Coots and Haven Gillespie and has been recorded by over 200 artists.
18. I’ve Got You Under My Skin
Following this initial success, Sinatra’s career had taken a downward turn by the early 1950s as his popularity waned and he went through various troubles in his personal life.
He turned a corner in 1953, however, when he signed a recording contract with .
Pairing him with the arranger and conductor , the label encouraged him to take a new direction focused on sophisticatedly swinging selections from the Great American Songbook, in a marked contrast to some of the second-rate novelty numbers he had recorded in recent years.
One of the great albums of this period is Songs For , a set of relaxed romantic numbers that are brilliantly orchestrated by Riddle.
‘I’ve Got You Under My Skin‘ is one of the most popular in his discography, with the crooner unfolding ‘s wry lyrics around that memorable refrain in the low wind parts, punctuated by a powerful trombone solo in the middle.
Sinatra’s great career revival around this time was also helped by his appearance in the film From Here To Eternity, for which he won an Oscar.
17.
Written by the classic songwriting partnership of Jimmy Van Heusen and lyricist by , was released by in 1959 on after appearing in the movie A Hole In The Head.
It’s just one of multiple occasions where Sinatra reached a mass mainstream audience via the cinema and reinforced his already burgeoning career and superstar credentials.
16. Only The Lonely
An innovative facet of Sinatra’s wildly successful run of albums for was his creation of some of the very first ‘concept albums’; records where all of the tracks contribute towards a unified narrative or theme.
One of these was For Only The Lonely, which followed in the footsteps of past releases like ‘In The Wee Small Hours’ and ‘Where Are You’.
It explores themes of heartbreak and despair. For, while things were now going well in a professional sense, Sinatra’s personal life was turbulent – he had recently finalised his divorce from , his second wife – while arranger had suffered the deaths of his mother and daughter.
The haunting title track, ‘Only The Lonely’ was written especially for the session by regular Sinatra contributors Jimmy van Heusen and lyricist .
The album’s -winning artwork, by Nicholas Volpe, features a painting of Sinatra made up as a tearful clown.
15. With Me
A more upbeat concept album, With Me was designed as a kind of musical trip around the world, with a number of geographically-themed songs featuring: ‘Brazil‘, ‘Moonlight In Vermont’, ‘On the Road to Mandalay’, ‘Blue Hawaii’ and so on.
The album contains some of the most influential which are instantly recognisable even to this day.
This album is notable as Sinatra’s first collaboration with the arranger Billy May. Whereas Riddle was known for his gorgeous string writing, May – a trumpeter himself – tended towards a punchier brass-laden sound.
The title track ‘ With Me’ – again composed for the occasion by van Heusen and Cahn – perfectly encapsulates Sinatra’s aura of easy-going charisma. The has become a favourite of crooners and singers, with covers from the likes of Kurt Elling, Eliane Elias and Curtis Stigers.
14. One For My Baby (And One More For The Road)
‘One For My Baby (And One More For The Road)’ is a booze-soaked classic of The American Songbook.
With music by Harold Arlen, ‘s lyrics – allegedly inspired by his own scandalous and ill-fated affair with a young Judy Garland – detail the protagonist’s romantic troubles whilst demanding more drinks from a fictional bartender named Joe.
Sinatra recorded the four times during his career, but this version is from the classic Live at the Sands album, another collaboration with the Basie Orchestra that was recorded in concert at the Sands Hotel and Casino in .
This particular track signals a rare moment of quiet intimacy during the programme, as Sinatra is accompanied solely by his long-standing regular pianist Bill Miller.
13. Strangers In The Night
With this 1966 hit, Sinatra started to abandon his usual swing aesthetic in favour of a driving contemporary pop sound.
This artistic decision was a success: the won multiple Grammy Awards and the album of which it was the title track became Sinatra’s most commercially successful yet.
Unlike, say, Ella Fitzgerald or Mel Torme, Sinatra was not an improvising scat singer.
However, towards the end of this track, with the music building to a crescendo, he memorably replaces the lyrics with the scat syllables “doo bee doo bee doo” before taking a short embellished vocal solo.
12. Change Partners
Sinatra made one of his most memorable collaborative albums in 1967 when he joined forces with the father of bossa nova, .
Bossa Nova – a fusion of Brazilian samba rhythms with sophisticated -influenced harmony – had taken the US by storm a few years earlier, with Stan Getz’s albums with Jobim and Joao Gilberto making a particularly big impact.
As it happened, Sinatra’s cool delivery was a perfect match for Jobim’s beautifully understated music .
With Claus Ogerman on conducting and arranging duties, we hear seven Jobim compositions, including eternal bossa favourites such as ‘The Girl From Ipanema’ and ‘Corcovado’, with Sinatra singing translated English lyrics, rather than the original Portuguese ones.
There are also three American Songbook tunes that are given bossa makeovers: ‘Baubles, Bangles and Beads’, ‘I Concentrate on You’ and Irving Berlin’s brilliant ‘Change Partners’, which works perfectly with a Brazilian twist.
11. In the Wee Small Hours of the Morning
Whilst Sinatra is perhaps best known for his brash, all-out swinging in front of a , his treatment of ballads has shaped the way countless singers since approach this type of .
In The Wee Small Hours of the Morning – composed by David Mann, with lyrics by Bob Hilliard – is just one such example of that, released in 1955 by .
10.
Whilst the style of has evolved over the decades, from to Motown to modern sounds, the fact that it is often built o songs has not.
Society may have indeed changed in the 70 or so years since Jimmy Van Heusen and wrote but Sinatra’s take on it in 1955 for sounds as fresh today as ever.
9. The
Whilst Sinatra’s version of many songs on this list are easily considered the definitive version, The has established itself as more of a standard.
With versions by a whole host of legendary musicians including Tony Bennett, Ella Fitzgerard, Paul Desmond and Errol Garner amongst others.
Despite all that, Sinatras 1964 version for Repreise Records stands out as a classic, enlisting to write the arrangement and provide the backings with his orchestra. It’s also regularly cited as one of the most popular songs of all time.
8. It Was a Very
As you probably know, many of the most famous songs of the 20th century started out as musical theatre compositions for Broadway.
Whilst the most famous versions were often changed substantially by musicians of the day, Sinatra occasionally gave them more of an authentic treatment.
His version of It Was A Very is a great example; its oboe introduction and sweeping string sections provide the platform for a pensive and theatrical performance of the Ervin Drake ballad.
Sinatra’s version actually won the for Best Male Vocal Performance in 1966.
7. Summer Wind
Another mid-60s release on , Summer Wind is perhaps one of the lesser-known Sinatra songs, but deserving of some attention nonetheless.
Originally written and released in Germany as ‘Der Sommerwind‘, re-wrote the into English along the same themes as the original.
It’s a beautiful showcase of the intricate orchestrations that typify the Sinatra style, as well as his vocal ability when it comes to swinging at medium-low tempos.
6. I’ve Got The World on a String
Even as early as the mid-fifties, musicians were looking back to the generation before for inspiration.
I’ve Got The World On A String was composed back in 1932 by Harold Arlen and Ted Koehler and got a revamp for Sinatra’s 1956 release.
It’s a sublime example of one classic Sinatra treatment: an out-of-tempo (‘colla voce’) introduction before the kicks into full swing.
5. Fly Me to the Moon
‘Fly Me to the Moon’ had already been covered by dozens of artists by the time that Sinatra put his stamp on it.
Might as Well Be Swing. The 1964 album was one of a number of collaborations the crooner made with ‘s fabulous orchestra, following on from Sinatra-Basie: An Historic Musical First.
Originally titled ‘In Other Words’, Bart Howard had first conceived of the as a waltz. However, it was repurposed as a toe-tapping 4/4 swinger for the Sinatra-Basie record by the arranger Quincy Jones, who would later go on to find fame as a songwriter and producer for Michael Jackson, among others.
Today the , with its famous opening lyrics – “Fly me to the moon and let me play among the stars” – is inextricably linked to the and is of course one of the most definitive .
Fans would clamour for him to perform it in concerts throughout his career.
4. That’s Life
Out of all the songs most famously associated with , That’s Life is perhaps one of the very best.
His version was released on in November 1966, just three years after it was first recorded by Marion Montgomery.
Written by Dean Kay and Kelly Gordon, it’s notable for the fairground-esque organ playing at the beginning and all-female backing vocals typical of that era.
3. The Best is Yet to Come
Composed in 1959 by Cy Coleman (music) and Carolyn Leigh (lyrics), made this classic his own with a 1964 release accompanied by and his orchestra.
The whole album – ‘It Might as Well be Swing‘ – is highly recommended, but this particular shows Sinatra at his hard-swinging best.
Ironically, it was the last that ever performed publicly (back in 1995) and the title lyric is etched on his gravestone in California, .
2. My Way
Like ‘Strangers In the Night’, ‘My Way’ has less of a -adjacent feeling to it than much of his earlier work, but it is certainly one of the most iconic , and perhaps the one that has made the greatest impact upon the wider public.
The number actually began life as ‘Comme d’habitude‘, a French pop written by Claude Francois and Jacques Revaux, before put English words to its melody.
With lyrics that look back nostalgically at a life of defiantly following one’s own path, it’s no surprise that ‘My Way’ is consistently cited as the number one most popular funeral for services and memorials.
And, like many of the on this list, it has been covered by dozens of artists – in this case, that includes the likes of Elvis Presley, Sid Vicious and Marvin Gaye! – but it is Sinatra’s version that is definitive.
1. ,
The that would become Sinatra’s last great hit was originally written for Liza Minnelli to perform in the Martin Scorsese film of the same name.
But it became one of Frank’s signature songs and a key part of his live repertoire when he recorded it on his 1980 album Trilogy: Past Present Future, upon which he combined a return to classic swinging American Songbook material with covers of contemporary pop numbers.
An ode to The City That Never Sleeps, there are few songs that have such iconic or instantly recognisable opening lines:
“Start spreadin’ the news, I’m leaving today.
I want to be a part of it: , .”
By the time died in 1998, he had sold more than 150 million records and won just about every award going, including the of Freedom (from ), the and the a year before his passing.
The quality of songs he recorded – and the style with which he performed them – have ensured that his legacy will live on a lot longer still in the realm of .
Thanks for joining us on this whistle-stop tour of Frank Sinatra’s incredible career. What have we missed from the list? Let us know your favourite Frank Sinatra songs in the comments below.
Fancy learning more about the greats of the swing era? Check out our article on the best big bands of all time and be sure to read our list of the top jazz singers in jazz history.
The label ‘Discover Jazz’ is attached to articles which have been edited and published by Jazzfuel host Matt Fripp, but have been written in collaboration with various different jazz musicians and industry contributors. When appropriate, these musicians are quoted and name-checked inside the article itself!
Although “Old Man River, is not jazz , song, it is my favorite Sinatra song. He, accompanied only by a piano, sang it with power, poignancy, and amazing voice control on live TV. Every time I see and hear him sing it, this magnificent performance brings tears to my eyes.
https://www.youtube.com/watch?v=HZse_nH1hSo&ab_channel=EdgardVitadePina