Frank Sinatra, a legendary American singer and actor, left an indelible mark on the world of music and entertainment. Born on December 12, 1915, in Hoboken, New Jersey, Sinatra rose to fame as the “Voice of the Century.” His velvet-smooth voice, impeccable phrasing, and charismatic stage presence made him an icon of the 20th century.
Sinatra’s career spanned over six decades, and he became one of the best-selling music artists of all time. Known for his timeless classics such as “My Way,” “Fly Me to the Moon,” and “New York, New York,” Sinatra’s contributions to the Great American Songbook are unparalleled. His ability to interpret lyrics with emotion and authenticity set him apart, earning him numerous awards, including multiple Grammys and an Oscar for Best Supporting Actor in “From Here to Eternity.”
Beyond his musical prowess, Sinatra made his mark in Hollywood, starring in acclaimed films like “The Man with the Golden Arm” and “Ocean’s 11.” A cultural icon, Sinatra’s charm extended beyond the stage and screen, as he embodied the spirit of the Rat Pack and an era of sophistication. Even in his later years, he continued to captivate audiences worldwide. Frank Sinatra’s legacy endures as a symbol of musical excellence and timeless elegance.
1. That’s Life
“That’s Life” is more than just a song; it’s an anthem that encapsulates the resilience, ups, and downs of the human experience. Originally recorded by Frank Sinatra in 1966, “That’s Life” became one of his signature tunes, resonating with its powerful lyrics and Sinatra’s emotive delivery.
The song’s lyrics, written by Dean Kay and Kelly Gordon, speak to the inevitability of facing challenges and setbacks in life, yet persevering with a sense of determination and acceptance. The triumphant refrain, where Sinatra belts out, “That’s life, that’s what all the people say, you’re ridin’ high in April, shot down in May,” captures the essence of life’s unpredictable nature.
Sinatra’s rendition of “That’s Life” showcases his vocal mastery, seamlessly blending swagger and vulnerability. The brass-heavy arrangement adds a dynamic and uplifting quality to the song, making it a timeless anthem for those navigating the unpredictable journey of life.
Over the years, “That’s Life” has endured as a classic, embraced by successive generations for its authenticity and relatability. Whether facing triumphs or setbacks, Sinatra’s rendition of “That’s Life” serves as a reminder to embrace the inevitable twists and turns with resilience and a sense of humor.
2. New York, New York
“New York, New York” is an iconic song that has become synonymous with the spirit and energy of the city it celebrates. Frank Sinatra’s rendition of the song, released in 1979, has become the definitive version, widely recognized and beloved.
The song, written by Fred Ebb and John Kander, captures the essence of New York City, its vibrancy, and its allure. Sinatra’s powerful delivery and impeccable phrasing bring the lyrics to life, creating an anthem that transcends time. The opening lines, “Start spreading the news, I’m leaving today, I want to be a part of it, New York, New York,” evoke a sense of excitement and possibility, reflecting the dreams that have drawn countless individuals to the city.
“New York, New York” gained even more prominence as the theme song for Martin Scorsese’s film of the same name, starring Robert De Niro and Liza Minnelli. Sinatra’s rendition is often played during celebrations and events, particularly in New York, where it has become an unofficial anthem for the city.
The song’s enduring popularity is a testament to its ability to capture the essence of New York’s unique energy and its universal appeal. Whether in Times Square on New Year’s Eve or on the streets of Manhattan, Sinatra’s “New York, New York” continues to evoke a sense of pride and excitement for the city that never sleeps.
3. Fly Me To The Moon
“Fly Me to the Moon” is a timeless classic that showcases Frank Sinatra’s unparalleled vocal artistry. Originally written by Bart Howard in 1954, the song gained widespread popularity after Sinatra recorded it for his 1964 album “It Might as Well Be Swing,” in collaboration with Count Basie and his orchestra.
The song’s lyrics speak of a romantic longing to escape to a celestial realm with a loved one. The opening lines, “Fly me to the moon, let me play among the stars, let me see what spring is like on Jupiter and Mars,” convey a dreamy and poetic sentiment. Sinatra’s smooth and emotive rendition, coupled with the lush orchestration, elevates the song to a level of sophistication that has made it a staple in the Great American Songbook.
“Fly Me to the Moon” has since become one of Sinatra’s signature songs, often associated with his performances. The song’s enduring popularity extends beyond Sinatra’s era, as it has been covered by numerous artists, further solidifying its status as a classic. Whether it’s heard in a jazz club, a romantic setting, or as part of a nostalgic playlist, “Fly Me to the Moon” continues to captivate audiences with its timeless charm and romantic allure.
4. Strangers In The Night
“Strangers in the Night” is another timeless classic associated with the legendary Frank Sinatra. Released in 1966 as the title track of Sinatra’s album, the song became an instant success and went on to win the Grammy Awards for Record of the Year and Best Male Pop Vocal Performance in 1967.
Written by Bert Kaempfert, Charles Singleton, and Eddie Snyder, “Strangers in the Night” is a romantic ballad that tells the story of two strangers who meet by chance and share a brief, passionate encounter. Sinatra’s interpretation of the song showcases his emotive and velvety voice, capturing the essence of a fleeting romantic moment. The song’s signature opening line, “Strangers in the night, exchanging glances,” has become iconic and instantly recognizable.
The orchestral arrangement, conducted by Nelson Riddle, contributes to the song’s romantic atmosphere, featuring a memorable trumpet solo. Sinatra’s delivery, marked by his impeccable phrasing and subtle vocal nuances, adds depth and emotion to the narrative. “Strangers in the Night” not only became one of Sinatra’s signature songs but also solidified his status as a master interpreter of romantic ballads. Decades after its release, the song continues to evoke a sense of nostalgia and remains a classic representation of Sinatra’s enduring legacy in the world of music.
5. My Way
“My Way” is a poignant anthem that has become synonymous with Frank Sinatra’s legacy. Released in 1969, the song was penned by Paul Anka, who reworked the French song “Comme d’habitude” into English, tailoring the lyrics to suit Sinatra’s life and career.
The lyrics of “My Way” reflect a retrospective perspective on life, expressing a sense of self-assurance, resilience, and a commitment to living authentically. The opening lines, “And now, the end is near, and so I face the final curtain,” set a reflective tone that resonates with listeners on a personal level. Sinatra’s emotive delivery adds depth to the lyrics, making the song a powerful introspective journey.
“My Way” became a defining moment in Sinatra’s career, serving as a reflection of his own life philosophy and a statement of individualism. The song’s universal appeal lies in its ability to connect with people across generations, as it encapsulates the universal human experience of facing challenges, making choices, and living with the consequences.
Sinatra’s rendition of “My Way” has been covered by various artists, but his version remains iconic. The song has been played at countless milestones and events, from weddings to funerals, attesting to its enduring impact and its status as a musical legacy that transcends time. “My Way” stands as a testament to Sinatra’s ability to deliver a song with emotional depth and authenticity, leaving an indelible mark on the world of music.
6. I’ve Got You Under My Skin
“I’ve Got You Under My Skin” is a classic song that has become synonymous with the incomparable voice of Frank Sinatra. Originally written by Cole Porter in 1936, the song gained widespread recognition and enduring popularity when Sinatra recorded his definitive version in 1956 for the album “Songs for Swingin’ Lovers!”
The lyrics of “I’ve Got You Under My Skin” convey the intense emotions of love, with the narrator expressing how deeply someone has become ingrained in their thoughts and emotions. Sinatra’s interpretation of the song is marked by his impeccable phrasing, smooth delivery, and a sense of sophisticated charm. His ability to convey both vulnerability and passion through his voice adds depth to the romantic narrative.
Nelson Riddle’s arrangement for the song is considered a masterpiece, featuring lush orchestration and a memorable instrumental opening. The song’s enduring appeal lies not only in Porter’s timeless lyrics but also in Sinatra’s unparalleled ability to breathe life into the music. The brassy horns and Sinatra’s velvet vocals create an irresistible combination that has made “I’ve Got You Under My Skin” a standard in the Great American Songbook.
Over the years, the song has been covered by various artists, but Sinatra’s rendition remains the quintessential version. It continues to be celebrated for its enduring elegance and contribution to the cultural legacy of both Sinatra and American popular music.
7. The Way You Look Tonight
“The Way You Look Tonight” is a classic song that epitomizes the timeless charm and romantic elegance of Frank Sinatra’s music. Written by Jerome Kern and Dorothy Fields, the song was originally composed for the 1936 film “Swing Time,” where it won the Academy Award for Best Original Song.
Sinatra’s rendition, released in 1964 as part of the album “Sinatra Sings Days of Wine and Roses, Moon River, and Other Academy Award Winners,” added a new layer of sophistication and intimacy to the song. His smooth and tender vocal delivery, accompanied by a lush orchestration, transformed the track into a quintessential love ballad.
The lyrics of “The Way You Look Tonight” express the joy and admiration one feels when captivated by the beauty of a loved one. Lines like “Someday, when I’m awfully low, when the world is cold, I will feel a glow just thinking of you and the way you look tonight” convey a timeless sentiment of love and devotion.
Over the years, the song has become a standard in the Great American Songbook and has been covered by numerous artists. However, Sinatra’s interpretation remains iconic, representing an era of romance and sophistication. “The Way You Look Tonight” continues to be a popular choice at weddings and romantic occasions, its melodic sweetness capturing the essence of enduring love.
8. Summer Wind
“Summer Wind” is a classic song that has become synonymous with the smooth voice and timeless style of Frank Sinatra. Originally written in German by Heinz Meier with English lyrics penned by Johnny Mercer, the song was first recorded by Wayne Newton in 1965. However, it was Sinatra’s rendition, released the same year on his album “Strangers in the Night,” that elevated the song to iconic status.
“Summer Wind” is a melancholic yet nostalgic ballad that reflects on the transient nature of a summer romance. Sinatra’s delivery captures the wistful and bittersweet emotions associated with the passing of time and the fleeting nature of love. His impeccable phrasing and emotional depth bring out the nuances of the lyrics, creating a memorable listening experience.
The orchestral arrangement, conducted by Nelson Riddle, complements Sinatra’s vocals with its gentle sway and evocative musical elements. The song’s atmospheric quality, coupled with Sinatra’s ability to convey a range of emotions, has contributed to its enduring popularity.
“Summer Wind” has since been covered by various artists, but Sinatra’s interpretation remains the definitive version. The song’s evocative lyrics, combined with Sinatra’s vocal mastery and Riddle’s lush arrangement, make “Summer Wind” a timeless classic that continues to resonate with listeners, conjuring images of romance and the passage of seasons.
9. I’ve Got The World On A String
“I’ve Got the World on a String” is a classic song that exudes optimism and a carefree spirit. Composed by Harold Arlen with lyrics by Ted Koehler, the song was introduced in the 1932 musical “Cotton Club Parade” and has since become a standard in the Great American Songbook.
Frank Sinatra’s rendition of “I’ve Got the World on a String” is particularly noteworthy. Released in 1953, Sinatra’s version showcases his trademark vocal style, combining swagger and charm. The song was part of his album “Songs for Young Lovers,” and Sinatra’s interpretation captured the post-World War II exuberance and a sense of hope for the future.
The lyrics convey a feeling of elation and triumph, with the protagonist expressing how everything in life is going their way. Lines like “I’ve got a song that I sing, I can make the rain go, any time I move my finger” exude confidence and a sense of being on top of the world.
“I’ve Got the World on a String” has been covered by various artists over the years, but Sinatra’s version remains a standout, encapsulating the spirit of optimism and the belief that anything is possible. The song is a testament to Sinatra’s ability to infuse joy and charisma into his performances, leaving an enduring impact on the world of music.
10. My Kind Of Town
“My Kind of Town” is a lively and celebratory song that Frank Sinatra made popular. Written by Jimmy Van Heusen and Sammy Cahn, the song was penned for the 1964 musical film “Robin and the 7 Hoods,” in which Sinatra starred alongside Dean Martin and Bing Crosby. The song went on to become a Sinatra classic.
The lyrics of “My Kind of Town” express a deep affection and pride for the city of Chicago, portraying it as a vibrant and welcoming place. Sinatra’s delivery is characterized by his trademark charm and enthusiasm, perfectly capturing the upbeat and optimistic spirit of the song.
The song features a lively big band arrangement, and Sinatra’s interpretation is accompanied by a dynamic musical backdrop. The combination of Sinatra’s charismatic vocals and the energetic orchestration gives the song an infectious quality that makes it both a joyful anthem and a tribute to the city it celebrates.
“My Kind of Town” has remained a favorite, not only for its catchy melody and Sinatra’s spirited performance but also for its association with Chicago and the broader notion of finding one’s ideal place. The song is a testament to Sinatra’s ability to infuse his music with a sense of joy and celebration, making it a beloved addition to his extensive repertoire.
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.
