Frank Sinatra, the legendary crooner and iconic figure of the 20th century, left an indelible mark on the world of music. With his velvety voice, impeccable phrasing, and charismatic stage presence, Sinatra captivated audiences for decades. His extensive discography boasts an array of timeless classics that continue to resonate with listeners of all generations. In this article, we embark on a journey through Sinatra’s illustrious career to uncover the Top 10 Best Frank Sinatra Songs of All Time. From heartfelt ballads that tug at the heartstrings to toe-tapping tunes that ignite the dance floor, Sinatra’s repertoire encompassed a wide range of musical styles and emotions. Each song on this esteemed list showcases Sinatra’s unparalleled artistry, showcasing his ability to convey raw emotion with every note he sang. Whether it’s the melancholic introspection of “My Way,” the infectious swagger of “Fly Me to the Moon,” or the tender romance of “Strangers in the Night,” these songs stand as testaments to Sinatra’s enduring legacy. Join us as we pay homage to the iconic performer and rediscover the extraordinary melodies that solidified Frank Sinatra as a true musical legend.
1. “Softly, As I Leave You”
With its beautifully melancholic lyrics and Sinatra’s captivating vocals, this classic ballad is a tribute to bittersweet memories. Released in 1964, "Softly, As I Leave You" became one of Sinatra’s most popular tracks with its emotional story of a lover departing from their significant other. The song's arrangement expertly captures the emotion of saying goodbye and moving on while still paying homage to the relationship at hand. It's no surprise that this song has become a timeless classic and remains a staple within Sinatra's catalog.
As listeners get lost in the song’s tender melody, they're transported back to those familiar feelings of longing and heartache that come with departing from someone you care about deeply. But what sets "Softly, As I Leave You" apart is how effectively it straddles the line between sadness and hopefulness. Instead of wallowing in despair, the track ultimately opts for a more upbeat outlook as it acknowledges life goes on after goodbyes are said.
One unique aspect of "Softly, As I Leave You" is the way it highlights Sinatra's vocal range. Throughout his career, he was known for his extraordinary voice control and ability to convey a wide range of emotions through his singing. This track showcases that versatility by allowing him to move effortlessly between mournful crooning and powerful belting.
Interestingly enough, there are some conflicting stories surrounding where Sinatra got his inspiration for this song. Some say it was written in collaboration with playwrights Hal Shaper and Antonio DeVito after they attended a performance called “The Futurists” in Italy. Others claim that DeVito wrote the original Italian version before Shaper translated it into English for Sinatra to record. Regardless of where it came from though, there's no denying that "Softly, As I Leave You" is one for the ages – a simply unforgettable masterpiece from one of music's greatest icons.
Sinatra's voice makes even Cupid himself jealous in this swoon-worthy classic.
2. “My Funny Valentine”
This classic ballad, known as "Valentine", showcases Sinatra's dynamic vocal range and emotional depth. The lyrics express both admiration and playful teasing towards a lover, making it a timeless piece for all lovers. With his smooth delivery and impeccable timing, Sinatra gives a poignant performance that has enthralled audiences for generations.
Sinatra recorded this song twice, in 1954 and again in 1961 with a more jazzy arrangement. The latter version is considered the definitive one and became a staple in his live performances. The melancholy trumpet solo in the middle adds to the haunting beauty of the track.
A notable cover of this song was done by Chet Baker, another legendary jazz performer.
Fun fact: "My Funny Valentine" was originally written for the musical Babes in Arms by Rodgers and Hart.
Frank's got a thing for tramps, but this song is definitely not about the homeless.
3. “The Lady is a Tramp”
This classic Frank Sinatra tune, recognized for its iconic opening line, is a lively and upbeat song that celebrates the free-spirited nature of the female protagonist. With lyrics that paint a vivid picture of her unconventional living style, “The Lady is a Tramp” captures Sinatra’s talent for storytelling in music. The song's swing-style orchestra arrangement adds to its charm and appeal.
Interestingly, although this song has been covered by many artists over the years, it continues to be strongly associated with Sinatra. His lively rendition of "The Lady is a Tramp" perfectly encapsulates his signature style and charisma. It's no wonder this song ranks among the best of his discography.
Did you know that while the initial run of "Babes in Arms," where the song appeared, was not as successful as anticipated, "The Lady is a Tramp" quickly became beloved by fans? Its popularity only grew after Sinatra recorded his version in 1957 for his album "A Swingin' Affair!" This goes to show how even songs that don't achieve immediate success can find their audiences eventually.
Even if you've never been to the Big Apple, listening to 'New York, New York' will make you feel like a seasoned New Yorker, or at least like you've watched enough episodes of Friends.
4. “New York, New York”
This iconic track, set in the backdrop of the bustling city of New York, embodies Frank Sinatra's admiration for his favorite metropolis and its vibrant energy. The song was composed by John Kander and Fred Ebb, with lyrics that highlight the unwavering spirit of the city and its aspirational movers. Launched in 1977, it became one of Sinatra's most celebrated songs, successfully evoking nostalgia for a place that is forever alive.
Sinatra's powerful vocals couple with an energetic melody to create an immortal composition that celebrates New York as a place where dreams come true. The track's chorus has become synonymous with celebrations worldwide, often played after athletic victories or festive occasions. Its opening line "Start spreading the news," has acquired legendary status within popular culture as an optimistic call to arms, encouraging people everywhere to forge ahead. Despite its age, "New York, New York" continues to inspire a sense of jubilation among audiences young and old.
Interestingly, while "New York, New York," is now forever associated with Sinatra's career and life legacy in pop culture history, it was initially written for Liza Minnelli to perform in Martin Scorsese's film "New York, New York." However, after hearing Sinatra perform the tune during one of his concerts in 1978; it was clear who deserved this musical masterpiece permanently: none other than Ol' Blue Eyes himself!
Sinatra's voice in 'Come Fly With Me' is so smooth, it could make turbulence feel like a joyride.
5. “Come Fly With Me”
This iconic crooner's "Come Fly With Me" is an enchanting tune that takes one on a magical journey. The lyrics and melody are perfectly harmonized, enabling the listener to imagine soaring through the skies with Sinatra's captivating voice.
The song was written by Sammy Cahn and Jimmy Van Heusen and speaks of traveling the world in luxurious fashion. Sinatra's delivery of this masterpiece won him critical acclaim and several awards.
This timeless piece showcases Sinatra's ability to take listeners on a romantic escapade, making it one of his best-known classics.
Interestingly, "Come Fly With Me" was initially intended for Bing Crosby before Frank Sinatra insisted that he would make something special out of it. So eventually, Cahn re-wrote the lyrics to suit Sinatra's unique style, which became an all-time hit sensation.
If Frank Sinatra sang me to the moon, I'd gladly leave earth behind.
6. “Fly Me to the Moon”
This timeless classic, which was later adopted as the theme song for the Apollo missions to the moon, is one of Frank Sinatra's most beloved songs. Its romantic lyrics and soulful melody have an enduring appeal that transcends generations, making it a fan favourite. With its iconic opening lines and mesmerising chorus, this song remains a gem in Sinatra's repertoire. The smooth orchestration adds to the magic of this tune, making it perfect for lounges, clubs, or just for a cozy evening at home.
In "Fly Me to the Moon," Sinatra croons about how he wants to experience love beyond Earth's boundaries and travel with his lover "…among the stars." Even after all these years since its release, the song conveys an innocent kind of love interlaced with space exploration. This track transports listeners on a dreamy journey laden with hope and possibility, evoking feelings of adventure and romance.
One little-known fact about “Fly Me to the Moon” is that it became part of Apollo 10’s official playlist in May 1969 –the mission in which NASA sent humans closest to land on the moon before Apollo 11. According to astronaut Thomas Stafford’s report about their trip on Lunar Module Snoopy, Frank Sinatra’s “Fly Me To The Moon” followed by Nat King Cole’s “The Very Thought Of You” were two tracks played during their ten-mile perigee lunar orbit!
Sinatra's crooning in 'I've Got You Under My Skin' will make you want to dance, or at the very least, itch for more.
7. “I’ve Got You Under My Skin”
This timeless classic, featuring on Frank Sinatra's 'Songs for Swingin' Lovers!' album, is a true masterpiece. The song, originally written by Cole Porter, was recorded by Sinatra in 1956 and has remained an all-time favourite for generations since. Its uptempo brass introduction leads to the memorable chorus that stays with the listener long after the tune has ended. "I’ve Got You Under My Skin" showcases Sinatra's iconic voice and impeccable phrasing, which were unmatched in his time.
Sinatra's version of this song stands out not only because it's one of Porter's most renowned compositions but also because of the way Sinatra brings it to life with unique tonality and soulful depth. His incredible performance elevates this track to something beyond words – it exudes passion and deep emotion that can be felt to this day.
It should be noted that despite its apparent romantic overtones, there is a metaphorical reading between the lines: the phrase "you're under my skin" refers not just to being deeply in love but also being addicted or obsessed with someone or something.
While many artists have tackled this song, no one does it quite like Sinatra. His attention to detail and mastery of vocal inflection make this rendition a standout hit that continues to delight listeners today.
Interestingly enough, during one particular concert performance of this song in 1962 at Carnegie Hall, Frank was suffering from a terrible cold and struggling to sing. However, despite his sickness, he delivered a mesmerizing rendition of the tune before collapsing backstage afterwards. This performance will forever remain one of his most memorable moments on stage.
Frank's singing will make you feel like you're dancing with a beautiful partner, even if you're just alone in your living room.
8. “The Way You Look Tonight”
This classic Frank Sinatra hit, number 8 on our list, captures the timeless essence of romance. With its memorable melody and lyrics written by Jerome Kern and Dorothy Fields, this song has stood the test of time and become a staple at weddings and other romantic events.
Sinatra's interpretation of the song is nothing short of magical, leaving listeners captivated and in awe. Sinatra's vocal range is showcased beautifully in this ballad, allowing him to convey a sense of vulnerability that is both sincere and endearing. The song's elegant orchestration enhances its romantic quality further, making it a truly unforgettable experience for listeners. It is no surprise that this song was awarded an Academy Award for Best Original Song in 1936 film 'Swing Time'.
Listeners can't help but feel transported back in time to the glamour and sophistication of old Hollywood whenever they hear this beloved classic.
One fascinating detail about “The Way You Look Tonight” is how Sinatra recorded multiple versions throughout his career, each bringing a unique perspective to the song's already timeless message. Despite its popularity as a slow dance tune at weddings today, when it was first released it became known as one of Sinatra's most upbeat tracks.
Don't miss out on the chance to experience the charm and magic of this Frank Sinatra classic – add “The Way You Look Tonight” to your playlist today! Even if you're not a fan of Sinatra, you'll still find yourself humming 'doo-bee-doo-bee-doo' after listening to 'Strangers in the Night'.
9. “Strangers in the Night”
This classic hit by Frank Sinatra, depicting romantic encounters with strangers at night, has captured the hearts of millions. The song was released in 1966 and won three Grammy Awards. Its melody also appeared in various films and TV shows, making it a timeless anthem of love and mystery.
Lyrics such as "Dooby dooby doo" and "Scooby dooby doo" add playfulness to the song's narrative. Sinatra's smooth vocals bring depth to the lyrics while keeping it light-hearted. It's said that he only recorded it because his daughter Nancy liked it, but it eventually became one of his most successful songs.
Interestingly, the iconic horn solo played by jazz artist Harry James was actually inspired by his own personal encounter with a woman on the street who blew him a kiss. This chance encounter led to the creation of one of the most recognizable melodies in music history – a perfect example of how inspiration can come from unexpected places.
Even if you hate Frank Sinatra, you still have to admit that 'My Way' is the perfect song to play at your ex's funeral.
10. “My Way”
Known as one of Frank Sinatra's greatest hits, this classic single is a must-have on any music lover's playlist. 'My Way' was composed by Paul Anka and originally written in French as "Comme d'habitude" before being revamped into the timeless piece we know today.
Sinatra's interpretation of the song became a signature tune for him, thanks to his powerful voice and incredible instrumental backing. The lyrics, which are all about living life with courage and without regret, resonate with listeners of all ages.
Sinatra's version of 'My Way' became an anthem for anyone who values independence, bravery and taking control of your own life. The song begins with a slow, contemplative piano melody before building up into an epic orchestration featuring trumpets, strings, drums and brass instruments in perfect harmony with Frank's singular voice. The arrangement gives the song its grandiose feeling and helps bring out the message behind the words.
What makes this track so special is that it speaks to people on a personal level. From blue-collar workers to politicians and celebrities, everyone can tap into its uplifting message of determination and self-reliance. Its stirring chorus has become iconic as well: "I did it my way," is a phrase that has been used time and again since Sinatra first belted it out over 50 years ago.
'My Way' encapsulates everything that made Frank Sinatra great: his unwavering confidence, his unparalleled vocal skills and his commitment to delivering unforgettable performances every time he sang. Whenever you hear this timeless classic play on the radio or at a wedding reception, you know that this is one of those tracks that will live on long after we're gone.