Frank Sinatra, known as “Ol’ Blue Eyes” and the iconic voice of the 20th century, left an indelible mark on the world of music. With his smooth vocal style, impeccable phrasing, and unparalleled charisma, Sinatra captivated audiences and solidified his place as one of the greatest performers in history. His discography is a treasure trove of timeless classics that continue to resonate with listeners across generations. In this article, we embark on a musical journey through the top 10 best Frank Sinatra songs of all time, celebrating the magic and brilliance of his extraordinary career.
From his early days as a big band crooner to his illustrious solo career, Sinatra’s catalog spans decades and encompasses a wide range of musical genres, including jazz, swing, ballads, and more. With his exceptional interpretive skills, Sinatra possessed the unique ability to infuse every lyric with heartfelt emotion, transporting listeners to a world of love, loss, and everything in between.
As we explore this illustrious collection, we will delve into the stories behind these iconic songs, examining the creative collaborations, memorable arrangements, and the personal significance they held for Sinatra himself. These selections are not only a testament to his unparalleled vocal talent but also a reflection of the cultural impact he had on the music industry.
So sit back, relax, and prepare to relive the enchantment of Sinatra’s timeless melodies as we count down the top 10 best songs that define his legendary career. From the swinging rhythms that will make you tap your feet to the tender ballads that will stir your soul, this compilation is a testament to the enduring legacy of Frank Sinatra, an artist whose music will continue to captivate audiences for generations to come.
1. “My Kind Of Town”
This timeless classic by Frank Sinatra exudes the familiar sentiment of a man singing about his favorite places around the world. “My Kind Of Town” depicts Sinatra's nostalgia for the city of Chicago and all its charm. The song is an upbeat celebration of the Windy City that brings out sentimental memories of belonging to a particular place and time, presented through a jazz-infused arrangement. Its vivid picture painting lyrics seamlessly blend with the joyful melody that leads to an unforgettable chorus.
With Sinatra's expressive voice perfectly complementing Sammy Cahn’s lyrics, “My Kind Of Town’ stands out as one of Frank Sinatra's most memorable pieces. While this track was made famous back in 1964, it remains timeless and appeals to people across generations.
Pro Tip: Listening to “My Kind Of Town” with headphones on can elevate your experience by immersing you in its jazzy vibe.
Summer might be over, but with 'Summer Wind' on your playlist, you'll always have a breeze (and a drink) in hand.
2. “Summer Wind”
This timeless classic, with its impeccable vocals and elegant instrumentation, is among the top 10 masterpieces by Frank Sinatra. Its romantic lyrics and whimsical melody summarize the essence of summer love. This song maintains a perfect balance between easygoing charisma and unparalleled musicianship. The exceptional saxophones in this tune can make anyone sway to its beats effortlessly – 'Summer Wind' is a masterpiece that sets the mood for any occasion.
Sinatra's got us under his skin with this classic hit – and we're perfectly okay with that.
3. “I’ve Got You Under My Skin”
This classic Frank Sinatra number, known to many as a masterpiece, is considered one of the Best Songs of All Time. “I’ve Got You Deep in the Heart of Me” would be an appropriate way to refer to this timeless tune that seamlessly blends Sinatra's crooning vocals with energetic brass sounds. This song features a choral group that adds depth and dimension to its overall appeal.
The melody has been covered by many artists over the years, but there's still nothing quite like Sinatra's interpretation of it. His nuanced and captivating vocals showcase his ability to effortlessly transition between different emotions throughout the song. The track was released back in 1956 but continues to inspire listeners today.
Additionally, fun fact: Despite being one of his most celebrated songs, “I’ve Got You Under My Skin” wasn't warmly received during its initial release. However, after a few lively performances on stage and some strategic airplay on the radio, it eventually gained popularity.
Sinatra’s smooth and sultry sounding "I’ve Got You Under My Skin" is forever etched into music history as one of his finest works that have stood the test of time.
Sinatra's smooth vocals in 'Strangers in the Night' will make you feel like you're in love, even if you're currently single and swiping left on Tinder.
4. “Strangers In The Night”
The timeless classic, sung by the legendary Frank Sinatra, is among the ten best songs of his career. The enigmatic "Those We Meet At Night" talks about two strangers who meet and fall in love in a chance encounter. The romantic melody and Sinatra's magic voice make it a complete charmer.
As one of Sinatra's most famous tracks, "Strangers In The Night" has become part of pop culture, with its memorable opening lines sung worldwide. Released in 1966, it became an instant hit reaching the top spot on Billboard Hot 100 chart. It also earned him a Grammy for Best Male Pop Vocal Performance.
Notably enough, even though the song talks about an anonymous couple's meeting at night, it was initially called "Broken Guitar." By incorporating his unique touch with the arrangement and saxophone solos by Don Costa, Frank created something new. While being a staple classic at dance parties to this day.
Sinatra interpreted more than 1500 efforts for music lovers that bewitched them with His Voice's charm.
Move over Empire State Building, "New York, New York" is now the official anthem of the city that never sleeps.
5. “New York, New York”
This particular song, often referred to as the anthem of New York City, has been featured in various movies and TV shows. Its upbeat tempo and catchy lyrics uplift the spirit of the listener. The song reflects not only a sense of pride and excitement for New York but also symbolizes ambition and determination to make it big in the city that never sleeps.
Being one of Sinatra's most iconic songs, “New York, New York” has rightfully earned its place in history. It was originally composed for the 1977 film "New York, New York", where De Niro and Liza Minnelli starred as musicians. This nostalgic melody conveys both hope and inspiration through its raw vocals and manic piano solos.
Listeners can witness how Sinatra sings each lyric with passion, emphasizing every word with his soulful voice. The energy behind the performance draws crowds to their feet, instantly creating an unbeatable ambiance. The song's lyrics highlight Manhattan's sights and sounds that bring out its unique identity.
To fully grasp the essence of “New York, New York”, we recommend listening to it while walking down the busy streets of Manhattan. It certainly makes for a thrilling experience as you can relate to the words so vividly portrayed by this legendary artist.
Life may be tough, but at least we have Frank Sinatra to sing about it.
6. “That’s Life”
This timeless classic, sung by the legendary Frank Sinatra, is a must-listen for fans of his music. It captures Sinatra's signature sound and style, with powerful vocals and an upbeat tempo. The lyrics speak of life's ups and downs, showcasing Sinatra's ability to convey emotion through his singing. The song has been covered by countless artists and remains popular to this day.
Sinatra delivers a poignant performance in "That's Life", showcasing his ability to connect with listeners on an emotional level. The song was released in 1966 and achieved great commercial success, reaching number 4 on the Billboard Hot 100 chart. It has since become one of Sinatra's most iconic songs, loved by fans across generations.
Listeners may be surprised to learn that the song was actually written by two relatively unknown composers – Dean Kay and Kelly Gordon. Despite this, it remains a beloved classic that continues to resonate with audiences today. Whether you're a longtime fan of Sinatra or just discovering his music, "That's Life" is a must-hear track that showcases his incredible talent as a performer.
Sinatra's voice sends listeners soaring to new heights in 'Fly Me To The Moon' – just don't forget your spacesuit.
7. “Fly Me To The Moon”
This iconic hit by Frank Sinatra, known as “Fly Me To The Moon,” has become a timeless classic loved by generations. This song, which was originally titled “In Other Words,” was famously played during the Apollo 11 mission to the moon in 1969.
It is said that the lyrics and melody of this song perfectly encapsulate the feeling of falling in love and being swept away to another world. Sinatra's smooth vocals and the jazzy sound of the brass instruments create a sense of sophistication and romance that still resonates with listeners today.
One unique aspect of this song is its use of a string section instead of a horn section, which was more common during that time. This choice gave the song a softer and more romantic tone, adding to its charm.
To fully appreciate “Fly Me To The Moon,” it is best to listen to it with someone special or while daydreaming about a romantic escape. The lyrics are simple yet poetic, and Sinatra's interpretation is flawless.
If you want to experience this classic hit in a new way, try listening to cover versions from different eras or genres. Each version adds something unique, proving once again the lasting power of this timeless melody.
Sinatra did it his way, but I still can't help wondering what the other options were.
8. “My Way”
One of Frank Sinatra's most iconic and timeless classics is a song that is often attributed to his legacy, and that is, “My Way”. This remarkable hit was initially written by Paul Anka and became one of Frank's signature songs. It provides an excellent insight into Frank's strong personality as he sings about living life on his terms confidently. The song has become an anthem of self-belief for generations and has been appreciated worldwide.
In the track “My Way”, Frank Sinatra conveys a message of self-acceptance, determination, and resilience as he insists on pursuing life on one's terms. His vocal delivery is unique and powerful, making it unforgettable each time it is performed. The emotional depth that Sinatra offers with this number can be experienced even today when listening to it.
Frank Sinatra's rendition of “My Way” diverse appeal lies in its essence of personal power, along with the smooth instrumental arrangement that complements his vocal abilities. The lyrics provide an inspirational message to take control over your own life and persevere despite adversities. Whether you're feeling down or enjoying success in life, this song offers encouragement to be brave always.
For fans who want more inspiration from 'The Voice' – Frank Sinatra will forever remain a legend through music history with songs like "Fly Me to the Moon," "Strangers in the Night," "New York New York", and so many more. These classics have an unparalleled status amongst avid music lovers across different ages due to their versatile themes and emotive performances. To experience the magic of Old Hollywood glamour through music should check out these remarkable pieces by the legendary crooner himself!
Sinatra could turn a love song into a seduction, and 'The Way You Look Tonight' is no exception – just be sure to wear your best lingerie when listening.
9. “The Way You Look Tonight”
This classic tune is one of the most iconic songs by Frank Sinatra. It is known for its romantic lyrics and soothing melody that captures the essence of falling in love. With its elegant charm, “The Way You Look Tonight” has become a timeless masterpiece that still reigns over the hearts of music lovers today.
Sinatra’s captivating voice brings out the beauty in this song as he sings about how his lover looks so enchanting when she walks into the room. The way he croons every word will make anyone believe in true love and feel like they are dancing under the stars.
Fun fact: This song was originally written for a 1936 movie called "Swing Time" and won an Academy Award for Best Original Song.
Overall, “The Way You Look Tonight” showcases Sinatra’s impeccable style and interpretation of music. It remains a must-listen classic for anyone who appreciates good music or just wants to fall in love all over again. You might not have the world on a string, but with Frank Sinatra's rendition, you'll feel like you do.
10. “I’ve Got The World On A String”
This classic Frank Sinatra song, with its upbeat and catchy tune, is a timeless masterpiece. Its lyrical content is reflective of Sinatra's success and the opportunities that he experienced throughout his life. The song describes how he feels like he can accomplish anything because the world is at his feet.
Sinatra's smooth and soulful voice, paired with the charming melody, makes this song an iconic piece of his legacy. The lyrics were penned by Ted Koehler and music composed by Harold Arlen in 1932.
Additionally, "I've Got The World On A String" was included in several later recordings by Sinatra such as the 1953 album 'Frankly Sentimental' and the 1966 release 'Sinatra At The Sands'. This indicates how much significance this particular track holds for him.
It is fascinating to note that although there are numerous interpretations of this classic, one prevailing theme is maintaining a positive attitude even when things might seem bleak. It has stood the test of time as one of Sinatra's most enduring hits.
Samuel Moore 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.
