Frank Sinatra, also known as “Ol’ Blue Eyes,” was an American singer, actor, and producer who is widely regarded as one of the greatest singers of all time. Born in New Jersey in 1915, Sinatra began his music career in the 1930s and quickly became a sensation for his smooth vocals and his unique phrasing.
Sinatra’s music is characterized by his distinctive voice, his ability to convey emotion through his singing, and his vast repertoire of songs. Some of his most famous songs include “My Way,” “Fly Me to the Moon,” and “New York, New York.”
Throughout his career, Sinatra released over 60 albums and won numerous awards, including multiple Grammy Awards and induction into the Grammy Hall of Fame and the Rock and Roll Hall of Fame. He was also known for his collaborations with other musicians, including Duke Ellington and Quincy Jones.
In addition to his music career, Sinatra was also an actor, appearing in films such as “From Here to Eternity” and “The Manchurian Candidate.” He was also involved in various philanthropic efforts, particularly those related to education and children’s charities.
Sinatra’s music and legacy continue to be celebrated and admired by fans and musicians around the world. He remains one of the most iconic and influential figures in the history of music, and his contributions to the genre will be felt for generations to come.
1. “My Kind Of Town”
This track's sweet serenade will take you on an upbeat, jazzy journey as Sinatra takes great pride in celebrating his 'kind of town' – Chicago! This song has an enduring charm that can transport listeners to the bustling city. Its catchy melody and joyous lyrics make it a legend of Frank Sinatra's discography that endures even today.
Sinatra describes this town as "the one that won't let you down", and he has managed to capture the essence of Chicago's soulful and romantic character into this piece. The song's optimistic tone celebrates the glory of Chicago's nightlife, people, and unique style, making it relatable to anyone who loves their hometown.
Listeners can enjoy the fantastic rhythm section while Sinatra pays tribute to his gratitude for Chicago – where he met his wife Nancy in a television studio greenroom. He croons about how the Windy City is where he feels most at home and how there isn't any place like it. This attribute makes it more personal than other numbers on this list.
'My Kind Of Town' showcases Sinatra's exceptional skills in bringing out the emotional complexity behind seemingly straightforward phrases. Its infectious chorus will have anyone singing along, tapping their feet, or humming to its beats long after it finishes.
This record remains a testament to Frank Sinatra's eternal love for Chicago and highlights why it deserves all the praises for being one of his trademark songs! Sinatra's got the world on a string, and this song's got me on the edge of my seat.
2. “I’ve Got The World On A String”
This classic Sinatra song, filled with romantic optimism and a lively tune is one of the most popular tunes in his repertoire. “I've Got The World On A String” features lyrics imbued with a sense of constant upward mobility. Released in 1953, this song reflects an era where America was basking in post-war prosperity and focused on achieving the American Dream.
Sinatra's rendition of “I've Got The World On A String” is an expression of a confident singer who knows how to carry an orchestra with just his voice. Although recorded by many artists over the years, Sinatra is perhaps the most celebrated for his version. With jaunty strings, swinging brass, and gentle background vocals that accompany his velvety voice, this song will surely make you tap your feet.
Interestingly, as Frank Sinatra gained mastery over his craft he began detaching himself from pop hits. But even so “I’ve Got The World On A String” remained one of those few numbers that stayed alive through multiple generations.
According to Billboard Magazine's Hot 100 chart archives(https://www.billboard.com/), "I’ve Got The World on a String" debuted on September 12th, 1953 and peaked at #14 in November of that year.
Summer may be over, but listening to 'Summer Wind' will make you feel like you're sipping a cocktail on a tropical island – without the sunburn.
3. “Summer Wind”
Sinatra's classic “Summer Wind” rendition is a timeless piece that stands out in its depth. Its sultry notes and rich lyrics make it one of the top picks amongst Sinatra's collection. The song takes us on a journey of love while encapsulating the essence of summer. The trumpet refrain with Sinatra's deep voice complements each other into a beautiful blend of melody that remains unbeatable to this day.
The ability of “Summer Wind” to transport the listener into another world has remained unparalleled, making it an all-time favorite globally. With its waltzing tune and lyrics that embody the season perfectly, listeners can't help but feel inclined towards dancing ever so gently along to this hit number.
It is worth noting that the song was composed by none other than Johnny Mercer, Hans Bradtke, and Henry Mayer, giving credit to every note invested in its creation. All three of them were leading names in music at their time, further emphasizing the magnificence behind every musical note and word.
Pro Tip: One could enhance their listening experience by attempting to visualize all the scenes mentioned in the song while playing it. This would help intensify emotions and create an everlasting reminiscence of an excellent classical masterpiece.
Sinatra's crooning in 'The Way You Look Tonight' is enough to make any ugly person feel beautiful.
4. “The Way You Look Tonight”
This Sinatra classic, with its memorable opening riff, earned him an Academy Award for Best Original Song. "The Way You Look Tonight" showcases Sinatra's vocal prowess and is widely regarded as one of his best. The song was written by Jerome Kern and Dorothy Fields and recorded by Sinatra in 1964.
Sinatra's iconic performance perfectly captures the charm, romance, and nostalgia of the song. His effortless delivery and emotional connection to the lyrics make this a timeless classic that remains popular today. Many artists have covered this song over the years, but few can match Sinatra's interpretation.
A fun fact about this song is that it was originally written for the 1936 movie "Swing Time" and was performed by Fred Astaire. It has since become one of the most recognized songs in American pop culture history.
Sinatra may have had his skin under control, but we all know we're powerless when it comes to falling under his musical spell with this classic.
5. “I’ve Got You Under My Skin”
This classic song is one of Frank Sinatra's trademark hits. With its jazzy rhythm and smooth vocals, 'I've Got You Deep In The Heart Of Me' is a timeless love song that has stood the test of time. The lyrics are full of romantic metaphors and imagery that transport listeners to the heights of passion and devotion. Sinatra's excellent rendition of the song remains just as popular today as it was when he first recorded it.
Sinatra captured the essence of love with this unforgettable hit that personifies his signature sound. The dramatic orchestration showcasing his deep, rich voice makes it impossible not to sing along with this iconic tune. Featuring the swaggering horns, Sinatra’s impeccable phrasing, and rhythmic groove, “I’ve Got You Under My Skin” remains one of the best songs by Ol’ Blue Eyes.
One unique aspect of this song is how the intro builds up the anticipation for an emotional finish. It has also inspired countless covers and adaptations across various genres and artists over time.
Pro Tip: To appreciate this classic Sinatra tune fully, take your time to savor each musical detail and feel every emotion conveyed in his silky-smooth voice – it will undoubtedly leave you spellbound!
Frank may have sung 'My Way', but let's be real, we're all singing it in the shower like nobody's watching.
6. “My Way”
This iconic tune about living life on your own terms and not regretting your decisions is one of Frank Sinatra’s most beloved songs. It showcases the crooning legend's trademark style and charisma. The song's uplifting, brassy arrangement and triumphant lyrics make it an anthem for those who refuse to live a mundane life.
"My Way" has remained a popular wedding song, graduation theme, and karaoke favorite since its release in 1968.
The lyrics encourage listeners to pursue their passions without fear or hesitation. The powerful message, combined with Sinatra's enchanting vocals, make for an unforgettable listening experience. The track has been covered by countless artists over the years, solidifying its enduring status in popular culture.
Interestingly enough, "My Way" was originally a French song called "Comme d'habitude." Paul Anka discovered the tune while visiting France and rewrote the lyrics to create the English version that Sinatra would record. Despite some initial reservations about the song's quality, Sinatra ultimately embraced "My Way," and it became one of his signature tunes.
Frank's crooning in 'Strangers in the Night' is so smooth, it’s like he’s serenading a stick of butter.
7. “Strangers In The Night”
This entrancing melody is a timeless classic from Frank Sinatra’s vast repertory. It is one of the most prominent songs he recorded during his career. With its chart-topping success, “Strangers In The Night” remains a fan-favorite to this day. The song's mellow melody and romantic lyrics will serenade you over and over again, eliciting an emotional response with each listen.
The haunting tune of “Strangers In The Night” provides a powerful platform for Sinatra's rich baritone voice to shine. Its memorable lyrics captivate listeners from the outset, creating an irresistible charm that ensnares every hearer in its web. This track showcases Sinatra at his finest, with his vocal power on full display, giving you an immersive listening experience.
Sinatra's rendition of “Strangers In The Night” stands out for its uniqueness in the way it presents love at first sight. It contrasts with the typical love-song style and creates a fresh perspective on romance, making it an unforgettable encounter that fans rave about regularly across generations.
Experience the enchanting magnetism of Frank Sinatra's poignant vocals as he belts out the lyrics to “Strangers In The Night.” Don't miss out on the chance to be swept away by this magnificent song that encapsulates great musicianship and effortless style.
He may have wanted to go to the moon, but at least Frank got us feeling all warm and fuzzy with this classic love song.
8. “Fly Me To The Moon”
This classic Sinatra song, infused with bossa nova rhythms and space-age pop-inspired arrangements, is a timeless masterpiece. “Fly Me to the Moon” is a tender love song that continues to charm new generations of listeners with its romantic imagery and hopeful lyrics. The upbeat tempo and Frank’s velvety vocals make this song a hit on dance floors everywhere.
Listeners can enjoy the nostalgic sounds of trumpets, violins, and muted brass instruments during the instrumental interludes. Sinatra's expressive delivery is impeccable as he croons the poetic verses that transport you to a world of imagination.
One interesting aspect of this track is that it was initially titled “In Other Words.” However, after Peggy Lee's recording of "Fly Me to the Moon" in 1960, Sinatra adopted it as his own title for later recordings.
To enhance your listening experience while enjoying “Fly Me to the Moon,” try these suggestions:
- Close your eyes and imagine yourself slowly swaying across a dance floor with your significant other.
- Let yourself get lost in the enchanting melodies of lush orchestration.
- Appreciate Frank’s smooth voice as he sings about taking you away on an imaginary journey through the stars.
Sinatra's ode to the city that never sleeps is so good, it could even make a New Yorker crack a smile.
9. “New York, New York”
This timeless classic, famously known as “The theme from New York, New York,” remains a symbol of the irresistible allure and energy the city embodies. Frank Sinatra’s impeccable voice brings to life John Kander's catchy tunes and Fred Ebb's lyrics in this story of hope and ambition in the city that never sleeps. The song originally appeared on the soundtrack for Martin Scorsese’s 1977 film “New York, New York”. Its popularity grew when Frank Sinatra recorded it two years later, turning it into an enduring anthem that has become synonymous with New York City.
In “New York, New York,” Sinatra captures the spirit of the city through his powerful vocals and charismatic swagger. The lyrics celebrate its uniqueness and resilience: “If I can make it there / I’ll make it anywhere / It’s up to you, New York, New York.” The upbeat tempo and memorable chorus infuse listeners with a sense of determination and excitement about what this vibrant metropolis has to offer.
Interestingly, despite being so closely associated with Frank Sinatra, “New York, New York” was actually first introduced by Liza Minnelli in Scorsese’s movie. However, it was Sinatra who elevated the song to another level with his passionate rendition. It went on to become one of his signature songs – closing nearly every live performance he gave from then on.
Don't miss a chance to experience an iconic tune that stands tall among other anthems celebrating American cities around the world. With its catchy melody and infectious optimism, there are not many songs that better embody all things NYC than “New York, New York.”
Sinatra's 'That's Life' is the perfect anthem for when life gives you lemons…and you just mix them with vodka and sing along.
10. “That’s Life”
This entry on the list of "10 Best Frank Sinatra Songs of All Time" goes to an iconic track titled "That's Life." With a soulful sound and Sinatra's unmistakable voice, it captures the ups and downs of life in a relatable yet inspiring way. The track was released in 1966 as part of an album of the same name and is widely regarded as one of Sinatra's best works.
It starts with a slow tempo and builds up to a powerful crescendo, complete with catchy horns and swinging drums. This dynamic arrangement perfectly matches the lyrics, which tell a story of perseverance through difficult times and seizing opportunities along the way.
One unique aspect of this song is that it doesn't shy away from the harsh realities of life but presents them with honesty and resilience. At its core, it's a message that even when things get tough, we should keep going and never give up.
To truly appreciate this track, listeners should pay attention to the subtle nuances in Sinatra's vocals. His delivery is full of emotion, from the soft moments where he croons about feeling low to the explosive chorus where he declares that he will keep fighting.
For those who are looking for inspiration or just want to groove along to some great music, "That's Life" is undoubtedly one of Sinatra's top songs that will leave you feeling uplifted and ready to take on whatever comes your way.
Edward Tomlin is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.
