Few artists bridge the gap between jazz and the wider public like ‘Ol’ Blue Eyes’. Here we take a look at 20 of the greatest Frank Sinatra songs from across his iconic career.

Frank Sinatra 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 jazz 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 jazz standard repertoire.

Ol Blue Eyes (as he was affectionately known) also collaborated with a number of important jazz musicians, including Count Basie and Duke Ellington, in an illustrious career that saw him lauded as one of the greatest singers of all time, as well as an academy award-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 Frank Sinatra discography is without a doubt his album Live at The Sands which you can find on Spotify, Youtube or your favourite record store.

20. I’ll Never Smile Again

Francis Albert Sinatra was born in 1915, to Italian immigrant parents in Hoboken, New Jersey. As a teenager, he became a fan of big band jazz, idolising Bing Crosby 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 Tommy Dorsey’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. Santa Claus is Coming to Town

No jazz 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 Merry Little Christmas…) but our favourite is his feel-good mid-tempo version of Santa Claus is Coming to Town.

Released in 1948 on Columbia Records, 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 Capitol Records.

Pairing him with the arranger and conductor Nelson Riddle, 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 Swingin Lovers, 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 Frank Sinatra songs in his discography, with the crooner unfolding Cole Porter’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. High Hopes

Written by the classic songwriting partnership of Jimmy Van Heusen and lyricist by Sammy Cahn, High Hopes was released by Frank Sinatra in 1959 on Capitol Records 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 Capitol Records 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 Frank Sinatra Sings 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 Ava Gardner, his second wife – while arranger Nelson Riddle 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 Sammy Cahn.

The album’s Grammy award-winning artwork, by Nicholas Volpe, features a painting of Sinatra made up as a tearful clown.

15. Come Fly With Me

A more upbeat concept album, Come Fly 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 Frank Sinatra songs 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 ‘Come Fly With Me’ – again composed for the occasion by van Heusen and Cahn – perfectly encapsulates Sinatra’s aura of easy-going charisma. The song has become a favourite of crooners and jazz 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, Johnny Mercer’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 song 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 Las Vegas.

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 song 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 jazz 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, Antonio Carlos Jobim.

Bossa Nova – a fusion of Brazilian samba rhythms with sophisticated jazz-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 big band, his treatment of jazz ballads has shaped the way countless singers since approach this type of song.

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 Capitol Records.

10. Love and Marriage

Whilst the style of pop music has evolved over the decades, from jazz to Motown to modern sounds, the fact that it is often built o love songs has not.

Society may have indeed changed in the 70 or so years since Jimmy Van Heusen and Sammy Cahn wrote Love and Marriage but Sinatra’s take on it in 1955 for Capitol Records sounds as fresh today as ever.

9. The Way You Look Tonight

Whilst Sinatra’s version of many songs on this list are easily considered the definitive version, The Way You Look Tonight has established itself as more of a jazz standard.

With versions by a whole host of legendary jazz 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 Nelson Riddle to write the arrangement and provide the backings with his orchestra. It’s also regularly cited as one of the most popular wedding songs of all time.

8. It Was a Very Good Year

As you probably know, many of the most famous jazz songs of the 20th century started out as musical theatre compositions for Broadway.

Whilst the most famous versions were often changed substantially by jazz musicians of the day, Sinatra occasionally gave them more of an authentic treatment.

His version of It Was A Very Good Year 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 Grammy Award for Best Male Vocal Performance in 1966.

7. Summer Wind

Another mid-60s release on Reprise Records, 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‘, Johnny Mercer re-wrote the song 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, jazz 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 Capitol Records release.

It’s a sublime example of one classic Sinatra treatment: an out-of-tempo (‘colla voce’) introduction before the big band 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 Count Basie’s fabulous jazz orchestra, following on from Sinatra-Basie: An Historic Musical First.

Originally titled ‘In Other Words’, Bart Howard had first conceived of the song 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 song, with its famous opening lyrics – “Fly me to the moon and let me play among the stars” – is inextricably linked to the American singer and is of course one of the most definitive Frank Sinatra songs.

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 Frank Sinatra, That’s Life is perhaps one of the very best.

His version was released on Reprise Records 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), Frank Sinatra made this classic song his own with a 1964 Reprise Records release accompanied by Count Basie and his orchestra.

The whole album – ‘It Might as Well be Swing‘ – is highly recommended, but this particular song shows Sinatra at his hard-swinging best.

Ironically, it was the last song that Frank Sinatra ever performed publicly (back in 1995) and the title lyric is etched on his gravestone in California, Los Angeles.

2. My Way

Like ‘Strangers In the Night’, ‘My Way’ has less of a jazz-adjacent feeling to it than much of his earlier work, but it is certainly one of the most iconic Frank Sinatra songs, 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 song written by Claude Francois and Jacques Revaux, before Paul Anka 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 song for services and memorials.

And, like many of the Frank Sinatra songs 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. New York, New York

The song 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: New York, New York.”

By the time Frank Sinatra died in 1998, he had sold more than 150 million records and won just about every award going, including the Presidential Medal of Freedom (from Ronald Reagan), the Grammy Legend Award and the Congressional Gold Medal 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 popular music.

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. Alternatively, we wrote about the life and career of his son, Frank Sinatra Jr.