Frank Sinatra is widely regarded as one of the greatest and most influential singers of the 20th century. Known as the “Chairman of the Board” or simply “Ol’ Blue Eyes,” Sinatra had a career that spanned over six decades, from the 1930s to the 1990s. He was a master of the Great American Songbook, recording timeless classics that have become standards of popular music. His signature smooth voice, impeccable phrasing, and ability to convey emotion through his singing made him a cultural icon and a beloved performer around the world.
Sinatra’s music has had a lasting impact on popular culture, influencing countless artists across genres. His songs continue to be covered and sampled in modern music, and his style and persona have been emulated by many. From romantic ballads to swinging big band numbers, Sinatra’s discography is filled with timeless hits that have stood the test of time.
In this list of the 10 best Frank Sinatra songs of all time, we will explore some of his most iconic recordings that showcase his talent and enduring legacy. These songs are not only essential parts of his catalog but also some of the most celebrated and beloved works in the history of popular music.
1. “That’s Life”
“That’s Life” is a classic song by the legendary crooner, Frank Sinatra. Released in 1966, the song quickly became a hit and has since become one of Sinatra’s signature tunes. With its upbeat tempo and positive lyrics, “That’s Life” is a timeless anthem about the ups and downs of life and the resilience needed to keep going through it all. Sinatra’s smooth vocals are perfectly suited to the song’s lyrics, which describe the trials and tribulations of everyday life, from heartbreak and disappointment to triumph and success. With its catchy melody and inspiring message, “That’s Life” remains a beloved classic in the American songbook and a testament to Sinatra’s enduring legacy as one of the greatest singers of all time.
2. “New York, New York”
“New York, New York” is one of Frank Sinatra’s most iconic songs, released in 1980 as the theme for Martin Scorsese’s film of the same name. The song’s catchy melody, brassy horns, and Sinatra’s powerful vocals capture the energy and excitement of New York City. The lyrics describe the city’s vibrancy and its promise of new beginnings, making it a beloved anthem for the Big Apple. The song has become a classic at sporting events, weddings, and other celebrations, and its popularity has only grown with time. With its upbeat tempo and Sinatra’s smooth delivery, “New York, New York” is a true classic and a testament to the enduring legacy of both Sinatra and the city he immortalized in song.
3. “Fly Me To The Moon”
“Fly Me To The Moon” is a timeless classic that showcases Frank Sinatra’s smooth and soothing vocals. Released in 1964, the song has become one of Sinatra’s signature tunes and is widely considered as one of the greatest jazz standards of all time. The song’s lyrics, written by Bart Howard, describe a romantic getaway to space, making it a perfect song for any couple in love. The upbeat tempo and soaring strings perfectly complement Sinatra’s silky voice, creating a dreamy and whimsical atmosphere. The song has been covered by numerous artists, but it is Sinatra’s rendition that stands the test of time. “Fly Me To The Moon” has been featured in numerous movies and television shows and is often played at weddings and romantic occasions. It is a testament to Sinatra’s enduring legacy as one of the greatest vocalists of all time and a true icon of American music.
4. “Strangers In The Night”
“Strangers In The Night” is a classic Frank Sinatra song that was released in 1966. It is a beautiful romantic ballad that captures the essence of a chance encounter with someone who has the potential to change your life forever. The song was composed by Bert Kaempfert, with lyrics by Charles Singleton and Eddie Snyder. It has a beautiful melody, with Sinatra’s voice soaring over the lush orchestration, delivering the poignant lyrics that speak of the possibility of love at first sight. The song became an instant classic and was one of Sinatra’s biggest hits, staying at the top of the charts for weeks. The memorable opening lines, “Strangers in the night, exchanging glances, wondering in the night, what were the chances?” have become iconic and instantly recognizable to generations of music lovers. The song has been covered by many artists over the years, but it is Sinatra’s version that remains the definitive rendition, capturing the essence of the romantic ballad with his signature style and timeless elegance.
5. “My Way”
“My Way” is a classic song by the legendary crooner Frank Sinatra, originally released in 1969. Written by Paul Anka, the song is known for its empowering lyrics about living life on one’s own terms, with Sinatra delivering a powerful vocal performance that captures the essence of the song. With its soaring melody and rich orchestration, “My Way” has become one of Sinatra’s most iconic songs, and a staple of his live performances. The song has been covered by numerous artists over the years, but it is Sinatra’s version that remains the definitive one, and a beloved classic of the American Songbook. “My Way” has also been used in various films and TV shows, cementing its status as a timeless classic that continues to inspire and captivate audiences today.
6. “I’ve Got You Under My Skin”
“I’ve Got You Under My Skin” is a classic song performed by Frank Sinatra. It was written by Cole Porter and was first recorded by Virginia Bruce in 1936. Sinatra’s version of the song was released in 1956 and became a hit. The song is a love song that talks about how the person is always on the singer’s mind and under his skin. The lyrics are romantic and the melody is beautiful, making it a timeless classic. Sinatra’s smooth and silky voice adds to the charm of the song, making it a favorite of many fans. The song has been covered by many other artists over the years but remains one of Sinatra’s most popular and beloved songs. It has been featured in several movies and TV shows and continues to be played on the radio and at events. The song has also been recognized as one of the greatest songs of all time and has been inducted into the Grammy Hall of Fame.
7. “The Way You Look Tonight”
“The Way You Look Tonight” is a classic love song performed by Frank Sinatra. Originally written by Jerome Kern and Dorothy Fields for the 1936 film “Swing Time,” it won the Academy Award for Best Original Song. Sinatra’s rendition, released in 1964, features lush orchestration and the crooner’s signature smooth vocals. The song describes the beauty of the person he loves, highlighting small details such as the way they smile and the way their hair falls. The romantic lyrics and melodic tune have made this song a favorite for weddings and romantic occasions. Sinatra’s rendition has been covered by numerous artists and has been featured in films such as “My Best Friend’s Wedding” and “Father of the Bride.” It is considered one of Sinatra’s most iconic songs and has cemented his place as a legend in the Great American Songbook.
8. “Summer Wind”
“Summer Wind” is a classic Frank Sinatra song that captures the essence of summer romance. The song was written by Johnny Mercer and Henry Mayer, and Sinatra first recorded it in 1966 for his album “Strangers in the Night.” The smooth and romantic melody is complemented by Sinatra’s signature crooning style. The lyrics describe a fleeting romance that is as fleeting as the summer wind, but the memories of the love affair linger on. The song has a dreamy quality that transports the listener to a nostalgic summer evening, evoking the feeling of being in love and the bittersweet realization that the season must eventually come to an end. “Summer Wind” has since become a beloved classic, covered by many artists and featured in various films and TV shows. It remains a staple of Sinatra’s discography and a testament to his ability to capture the essence of love and romance in his music.
9. “I’ve Got The World On A String”
“I’ve Got The World On A String” is a classic Frank Sinatra song released in 1953, and it quickly became one of his signature songs. The upbeat and jazzy tune was composed by Harold Arlen and Ted Koehler and has been covered by many artists over the years. Sinatra’s smooth and charismatic vocals perfectly capture the song’s optimistic and confident lyrics about having everything under control and feeling on top of the world. The song’s big-band instrumentation and lively tempo create a joyful and celebratory mood that is impossible not to tap your feet to. The song has since become a standard of the American Songbook and a staple of Sinatra’s repertoire. The song’s memorable opening lines, “I’ve got the world on a string, sitting on a rainbow,” have become iconic in popular culture and are often associated with Sinatra’s charismatic persona. “I’ve Got The World On A String” is a timeless classic that perfectly captures the spirit of the 1950s, and it still resonates with audiences today as a symbol of triumph and optimism.
10. “My Kind Of Town”
“My Kind of Town” is a classic song from Frank Sinatra, released in 1964. The song was written by Jimmy Van Heusen and Sammy Cahn, who were frequent collaborators with Sinatra. The track features a swinging jazz orchestra and Sinatra’s smooth vocals, making it a staple of his live performances. The lyrics pay homage to the city of Chicago, with references to popular landmarks and cultural icons, such as the Wrigley Building and Al Capone. The song’s upbeat tempo and catchy melody have made it a popular choice for films, television shows, and commercials. Sinatra’s version of “My Kind of Town” has become an enduring classic, and a beloved anthem for anyone who loves the Windy City or just enjoys a good, old-fashioned swing tune.