Frank Sinatra, also known as “Ol’ Blue Eyes,” was one of the most influential and iconic musicians of the 20th century. Born in Hoboken, New Jersey in 1915, Sinatra’s career spanned over six decades, during which he became renowned for his unique vocal style, impeccable phrasing, and charismatic stage presence. He was not only a talented singer, but also a skilled actor, winning an Academy Award for his performance in “From Here to Eternity” in 1953.
Sinatra’s music has had a lasting impact on popular culture, with his songs still being widely recognized and appreciated today. From romantic ballads to upbeat swing numbers, his repertoire included a diverse range of musical styles, making him a beloved figure across generations. In this article, we will be highlighting the 10 best Frank Sinatra songs of all time, each of which showcases his remarkable talent and artistry.
Whether you’re a die-hard fan or new to Sinatra’s music, this list will guide you through some of his most memorable and timeless hits. From the iconic “My Way” to the swinging “Fly Me to the Moon,” these songs continue to captivate audiences with their lyrical depth, emotional resonance, and unparalleled musicality. Join us as we celebrate the life and legacy of one of the greatest singers of all time and explore his top 10 songs that have left an indelible mark on music history.
1. Fly Me To The Moon
“Fly Me to the Moon” is a classic jazz standard written by Bart Howard in 1954. It has since been covered by numerous artists, including Frank Sinatra, who popularized the song with his 1964 rendition. The song features a swinging melody and upbeat tempo, with lyrics that express a desire for adventure and a longing to escape the mundane. Sinatra’s smooth vocals and impeccable phrasing perfectly capture the song’s romantic and whimsical spirit, making it a timeless favorite among jazz and pop music fans alike. “Fly Me to the Moon” remains one of Sinatra’s most iconic and enduring songs, with its catchy tune and playful lyrics inspiring listeners to dream big and reach for the stars.
2. My Way
“My Way” is a classic pop song written by Paul Anka, with lyrics based on the French song “Comme d’habitude.” Frank Sinatra’s 1969 recording of the song has since become an iconic anthem, with its lyrics expressing a sense of individualism, self-confidence, and a willingness to take risks. The song’s sweeping melody and powerful orchestration perfectly complement Sinatra’s emotional and impassioned vocal performance, making it a standout track in his extensive repertoire. “My Way” has since become a cultural touchstone, with its lyrics resonating with listeners as a celebration of personal freedom and self-expression. The song’s enduring popularity has cemented its place as one of Sinatra’s most beloved and recognizable hits.
3. Summer Wind
“Summer Wind” is a classic pop song originally recorded by Wayne Newton in 1965, but it was Frank Sinatra’s 1966 recording that made it a hit. The song’s breezy melody and wistful lyrics evoke a sense of nostalgia and longing, with its themes of love and loss capturing the bittersweet feelings of a summer romance. Sinatra’s smooth and mellow vocals perfectly convey the song’s sentimental and romantic mood, backed by lush orchestration that enhances its dreamy quality. “Summer Wind” has since become a beloved classic, with its timeless appeal making it a staple on radio playlists and in movies and TV shows. The song remains a testament to Sinatra’s enduring talent and his ability to capture the essence of a song with his emotive and expressive voice.
4. The Way You Look Tonight
“The Way You Look Tonight” is a classic pop song written by Jerome Kern and Dorothy Fields for the 1936 film “Swing Time.” The song has since become a timeless favorite, with its sweet and romantic lyrics celebrating the beauty and charm of a loved one. Frank Sinatra’s 1964 recording of the song has become one of the most iconic versions, with his smooth and intimate vocals perfectly capturing the song’s tender and affectionate tone. Backed by a lush orchestration that features a soaring string section, Sinatra’s rendition of “The Way You Look Tonight” is a testament to his artistry as a singer and his ability to convey the heartfelt emotions of a song. The song remains a cherished classic, with its lyrics and melody continuing to inspire feelings of love and adoration.
5. I’ve Got You Under My Skin
“I’ve Got You Under My Skin” is a classic pop song written by Cole Porter in 1936. The song has since become a jazz standard and has been covered by many artists, but it was Frank Sinatra’s 1956 recording that made it a hit. The song’s infectious melody and upbeat tempo belies its lyrics’ darker tone, with the song expressing the feeling of being deeply in love with someone to the point of obsession. Sinatra’s dynamic and passionate vocal performance perfectly captures the song’s intense emotions, backed by a driving rhythm section and a jazzy horn arrangement. “I’ve Got You Under My Skin” has since become one of Sinatra’s most iconic hits, with its memorable melody and lyrical depth making it a standout track in his extensive discography. The song remains a beloved classic, with its timeless appeal and emotional resonance making it a favorite among jazz and pop music fans alike.
6. I’ve Got The World On A String
“I’ve Got the World on a String” is a classic pop song written by Harold Arlen and Ted Koehler in 1932. Frank Sinatra’s 1953 recording of the song has since become one of the most popular versions, with his swinging and upbeat performance capturing the song’s optimistic and carefree spirit. The song’s lyrics express a feeling of exuberance and confidence, with the singer proclaiming that they have everything they could possibly want. Sinatra’s effortless and charismatic vocal delivery is backed by a lively big band arrangement, featuring horns, drums, and a swinging rhythm section. “I’ve Got the World on a String” has since become a beloved classic, with its infectious melody and uplifting lyrics inspiring feelings of joy and positivity. The song remains a testament to Sinatra’s talent and his ability to bring a song to life with his dynamic and charismatic performances.
7. That’s Life
“That’s Life” is a classic pop song written by Dean Kay and Kelly Gordon in 1963. It was Frank Sinatra’s 1966 recording of the song that made it a hit and an anthem for persevering through life’s ups and downs. The song’s lyrics express a sense of resilience and determination, with the singer acknowledging that life can be tough but ultimately affirming that they will overcome any obstacles. Sinatra’s passionate and soulful vocals are backed by a driving big band arrangement, featuring horns, drums, and a powerful brass section. “That’s Life” has since become one of Sinatra’s most iconic hits, with its empowering message and powerful vocal performance inspiring listeners to keep pushing forward despite adversity. The song remains a beloved classic, with its timeless appeal and emotional resonance making it a favorite among fans of jazz and pop music.
8. New York, New York
“New York, New York” is a classic pop song written by John Kander and Fred Ebb for the 1977 film of the same name. It was Frank Sinatra’s 1980 recording of the song that made it an iconic anthem for the city that never sleeps. The song’s catchy and upbeat melody, backed by a driving big band arrangement, perfectly captures the energy and spirit of New York City. Sinatra’s powerful and dynamic vocal performance exudes confidence and charisma, making the song a beloved classic and a staple at parties and events. “New York, New York” has since become an enduring symbol of the city’s vitality and cultural significance, with its lyrics and melody inspiring feelings of excitement and nostalgia. The song remains a testament to Sinatra’s lasting impact on pop culture and his ability to capture the essence of a place and a moment with his music.
9. My Kind Of Town
“My Kind of Town” is a classic pop song written by Jimmy Van Heusen and Sammy Cahn for the 1964 film “Robin and the 7 Hoods.” It was Frank Sinatra’s 1964 recording of the song that made it a hit and an anthem for the city of Chicago. The song’s upbeat tempo and swinging melody capture the city’s lively and vibrant spirit, while Sinatra’s smooth and charismatic vocals celebrate the city’s unique charm and character. The song’s lyrics express a sense of hometown pride and affection, with the singer declaring that Chicago is his kind of town. “My Kind of Town” has since become a beloved classic, with its infectious melody and heartfelt lyrics making it a favorite among fans of jazz and pop music. The song remains a testament to Sinatra’s ability to capture the essence of a place and a moment with his music, cementing his legacy as one of the greatest singers of all time.
10. Strangers In The Night
“Strangers in the Night” is a classic pop song written by Bert Kaempfert, Charles Singleton, and Eddie Snyder in 1966. Frank Sinatra’s 1966 recording of the song has since become one of the most popular and recognizable versions, with its smooth and romantic melody and its lyrics about a chance encounter between two strangers. Sinatra’s suave and sophisticated vocal performance is backed by a lush and dreamy orchestration, featuring sweeping strings and a jazzy horn arrangement. “Strangers in the Night” has since become a beloved classic, with its timeless appeal and emotional resonance making it a favorite among fans of jazz and pop music. The song remains a testament to Sinatra’s talent and his ability to bring a song to life with his emotive and expressive performances.
