Described by many journalists and music critics as “the greatest singer of the 20th century,” Hoboken, New Jersey-born Frank Sinatra came from humble roots and a big Italian immigrant family. With his silky smooth pipes and manicured image portraying a ladies’ man among bright, metropolitan lights, he became an enduring musical force throughout the 1940s and into the 1960s.
With a marathon of a music and acting career, he set himself up to be an integral part of “The Rat Pack,” a group of big band performers with dazzling shows and show-stopping parties. Racking up hit after hit, Sinatra eventually became one of the world’s best-selling music artists.
With over 150 million in album sales under his belt over the course of his career, let’s unpack the best Frank Sinatra songs to ever grace the airwaves.
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11. Night and Day
Originally written by Cole Porter, ‘Night and Day’ drew high praise from one of the 20th century’s most in-demand composers, Irving Berlin. The ‘White Christmas’ author loved the tune so much, he wrote Porter congratulating him on “the best tune of the year” after its release in 1932. The tune was written for the Fred Astaire play and film project, The Gay Divorce, but when Frank Sinatra decided to cover it, he reworked it in such a way that made it all his own. He changed some of the lyrics, as he tended to do with the Porter songs he covered, and added his whimsical touch to the overall feel of the romantic ballad. This gentle love note of a song was Sinatra’s first hit as a solo artist.
10. Theme from New York, New York
One of New York City’s best-known theme songs, the inspiring and upbeat big band tune ‘New York, New York’ was a perfect one for Sinatra to tackle. It was in keeping with his cosmopolitan image, and he capitalized on the song’s previous success as the theme to the popular film by the same name starring none other than cabaret queen Liza Minnelli. A dazzling ode to The Big Apple, Sinatra started incorporating it into his live shows in ’78, and fans quickly took to his anthemic version. He had been experiencing a bit of an artistic slump in the previous few years, but this single helped reignite his career, much like what happens to the main character in the song, who leaves a small, quiet town to discover magic and mystery among the bright lights of New York City.
Recommended: Our pick of the best songs about New York (this one is included, naturally 🙂
9. You Make Me Feel So Young
Sinatra’s silky smooth appeal and crystal blue peepers game him the suave nickname, “Ol’ Blue Eyes.” His effortless charisma is in fine form with one of his earlier beloved tracks ‘You Make Me Feel So Young.’ Making the rounds since it was first published in 1946 for a musical, Ol’ Blue Eyes recorded it about 10 years later, and it soon set itself apart as one of his signature singles. He often performed it live, with shows often taking place in big cities like New York City and desert destination, Las Vegas. He often traveled and performed with a group of fellow big band artists like Dean Martin and Sammy Davis, Jr. Their dominance among the entertainment industry throughout the 1950s and their notorious, expensive after-show parties earned them a collective nickname, “The Rat Pack.”
8. Come Fly With Me
Written by two WWII-era songwriters who shared a passion for flying, both Jimmy Van Heusen and Sammy Cahn penned ‘Come Fly With Me’ with Ol’ Blue Eyes in mind. The orchestral track beckoning listeners to embrace Sinatra’s jet-setter lifestyle and fly away with him really resonated with his debonair image and the fans who adored him. It was also the title track for a new kind of musical release, the “concept album,” which Frank championed. Instead of a bunch of different tracks playing one after the other with different tempos, subject matter, and instrumentation, the Come Fly Away With Me album as a whole centered around travel, with his trademark big band sound and easy-going song pace present throughout each number.
Recommended: Some more songs about traveling together.
7. I’ve Got You Under My Skin
Sinatra scored a big hit with another Cole Porter-written track when he released ‘Ive Got You Under My Skin.’ As he did with many of his songs, Porter originally wrote the tune for a musical from the 1930s. Frank was a big fan of the number and worked hard in the studio to put his own spin on it so it sounded like an authentic Sinatra recording. After 22 takes, he felt he properly captured the song’s charming, intimate essence. The creatively-written song is something of a plot twist. Normally, when someone’s managed to get under your skin, you’re irritated with them. But Porter reimagines the saying by conveying the fact that a woman has gotten under a man’s skin in a good way. He’s head over heels for her. ‘I’ve Got You Under My Skin’ ultimately became a pop standard, with many big artists recording it, from Ella Fitzgerald to Michael Buble.
Recommended: Check out the original Cole Porter version on our best songs from the 1930s list.
6. The Way You Look Tonight
One of America’s most cherished pop standards from the Tin Pan Alley era, ‘The Way You Look Tonight’ was first recorded by one of the early 1900’s biggest stars, Fred Astaire. Penned by popular composers Dorothy Fields and Jerome Kern, Astaire first performed it during an understatedly romantic scene in his movie, Swing Time. Quite the interpreter, Sinatra took a crack at it and naturally came up with his own sought-after version. Not only did the single become one of his many signature releases, but his rendition became a longstanding part of America’s pop culture history since the big band singer released it in 1964. The popular wedding song has been used in countless films and TV shows, and even played a key role in a Michelob beer commercial in the late ’80s. Sinatra preferred Martinis, but the payment he received from the advertisement probably looked pretty good to him too.
Recommended: Our pick of the most romantic songs ever written.
5. Strangers In The Night
There is so much to unpack with this surprise hit for Sinatra after over a decade of being kept out of the top spot on the charts by rival releases. A number one hit in both America and the UK, Ol’ Blue Eyes actually despised this song so much, he never included it in a live set unless he had to. Shocking, given that this was one of his most successful numbers. For the lyrics, he actually came up with the improvised “scat” line, “Dooby dooby doo.” In a pretty remarkable turn of events, animator Iwao Takamoto just happened to be a Sinatra fan, and after hearing the closing adlibbed line in the song, got inspired to create the loveable, crime-fighting pooch Scooby-Doo, who made his debut in ’69, three years after Sinatra’s hit was released.
Recommended: Our list of the most iconic 1960s music (which includes this gem.)
4. That’s Life
“I’ve been a puppet, a pauper, a pirate, a poet, a pawn and a king.” Songwriter Dean Kay was present for Sinatra’s recording session for this school-of-hard-knocks song that finds the crooner looking at adversity in a positive light. Frank was known for his exceptional skills in the studio, often recording songs all the way through in one take, no need for editing. However, Kay’s story goes that with ‘That’s Life’ Sinatra’s producer decided at the last minute the singer needed to re-record the vocals. This didn’t sit well with Sinatra, who felt he got it right the first time. Nevertheless, the perfectionist made his way back to the microphone to record another take. This last take is the infamous one you hear on albums, with Frank’s surprising “bite” added to his performance. As it turns out, this extra vocal punch was perfect for the message of the tune. He scored another top five hit with the single release.
Recommended: Our pick of songs about life’s journey.
3. Somethin’ Stupid
Part of Frank Sinatra’s legendary legacy is found with his daughter Nancy, who carried on her father’s torch by becoming a successful singer in her own right. With ‘Somethin’ Stupid,’ Frank performs a rare duet with his daughter, and the two showcase how their vocals blend effortlessly together by singing every lyric simultaneously, harmonizing the entire time instead of trading off phrases. A huge hit in the states and across the pond, ‘Somethin’ Stupid’ tackles complicated love affairs, and how those three little words, “I love you,” can have such a big impact on relationships that are already on shaky ground. Sinatra was able to add yet another accolade to his long list of accomplishments with this single. Climbing to number one both nationally and internationally, it became the only father-daughter collaboration to ever do so in the history of the American Hot 100 Billboard charts. It wasn’t until 2003 that Nancy and Frank were ousted by father-daughter duet Ozzy Osbourne and Kelly with their single ‘Changes.’
2. Fly Me To The Moon (In Other Words)
Originally titled ‘In Other Words,’ this cabaret-laden tune was given the swinging jazz-inspired Sinatra treatment when he got ahold of it. Though others like Tony Bennett have recorded the tune as well, Frank’s is still considered to be the authoritative rendition. An unmistakable love song that finds The Big Guy comparing the love he feels for his flame to flying among the moon and stars, his recording reveals a slightly peppier delivery than usual. He had good reason for that. Frank decided to record ‘Fly Me To The Moon’ when he was about to marry the young starlet Mia Farrow. Record producer Quincy Jones helped add to the recording as well by bringing in the popular Count Basie Orchestra for the song’s smooth, springy instrumental pieces.
Recommended: Our heartwarming list of old songs about love.
1. My Way
While ‘That’s Life’ conveys an extra bite to Sinatra’s vocal performance, there’s an air of desperation in his delivery of the anthemic UK hit, ‘My Way.’ Released in ’69 when the music industry was experiencing a dramatic evolution in a post “summer of love” America, the song was born from a dinner conversation between Frank and fellow musician Paul Anka. He and Anka had become friends over the years, and Sinatra confessed to him he was quitting the business for good, feeling like he couldn’t compete with the trends of the day. Drawing on that, Anka took an old French song and re-wrote the lyrics, creating a story of a headstrong man who went out with in a blaze of glory because he never caved to surrounding pressures. It became a trademark track for Sinatra, and the over-saturation didn’t sit well with him. He confessed quite a few times in interviews it became one of his least favorite singles because it came to feel “self-indulgent.” Though this can be commonplace with artists who have to sing their biggest songs ad nauseum, the tune’s timeless message unmistakably resonated with society. It is a song that continues to influence contemporary cultures today in some of the entertainment industry’s most popular works, like mobster classic show The Sopranos, and some of music’s most eclectic bands like The Sex Pistols, whose own Sid Vicious recorded a particularly pained, melancholy version that still rumbles along the outskirts of the historic punk movement even today.
Recommended: More classic songs everyone knows.
Every Sinatra fan has their own “top 500-or-more” list of his songs. One of my favorites is “All or Nothing At All” backed by Riddle – you really have to intently listen to each section of instrumentation to appreciate the artistry of vocalist and arrangement.