Frank Sinatra, born on December 12, 1915, in Hoboken, New Jersey, emerged as one of the most influential and admired entertainers of the 20th century. Renowned for his smooth, rich voice and impeccable phrasing, Sinatra transformed the art of popular singing. His career, spanning over five decades, was a tapestry of triumphs in music, film, and live performance.
Sinatra’s journey to stardom began in the swing era with Harry James and Tommy Dorsey, but he soon soared as a solo artist, becoming the idol of the “bobby soxers.” His ability to convey profound emotion in songs like “In the Wee Small Hours of the Morning” and “One for My Baby” resonated deeply with listeners, establishing an intimate bond that few artists have achieved.
Beyond music, Sinatra’s charisma shone on the silver screen, earning him an Academy Award for his performance in “From Here to Eternity.” His persona, marked by a blend of toughness and vulnerability, defined the quintessential American swagger and sophistication.
Off-stage, Sinatra’s life was as dramatic as his songs, marked by tumultuous romances, rumored connections with the Rat Pack and the mob, and a relentless pursuit of social justice. His legacy, however, is firmly anchored in his music – the timeless tracks that continue to captivate and inspire generations, ensuring that the legend of Frank Sinatra endures as a cornerstone of American cultural heritage.
1. That’s Life
“That’s Life” is a poignant anthem that captures the essence of resilience and human perseverance, immortalized by Frank Sinatra’s powerful rendition in 1966. Written by Dean Kay and Kelly Gordon, the song stands as a testament to the relentless ebb and flow of life’s fortunes and adversities.
With Sinatra’s dynamic and soulful delivery, “That’s Life” resonates as a bold declaration of defiance against life’s inevitable trials and tribulations. The lyrics eloquently depict the journey of an individual who, despite facing numerous setbacks, refuses to succumb to defeat. The song’s narrative ranges from moments of despair to heights of triumph, encapsulating the idea that life’s challenges are not just to be endured but confronted head-on.
The chorus, with its memorable lines, “I’ve been a puppet, a pauper, a pirate, a poet, a pawn, and a king,” illustrates the myriad roles one might play in the grand theater of life. Sinatra’s interpretation, characterized by his impeccable timing and phrasing, infuses the song with a gritty optimism and a swaggering confidence.
“That’s Life” struck a chord with audiences worldwide, becoming a staple in Sinatra’s live performances and a beloved classic in the Great American Songbook. Its universal message of persistence, coupled with Sinatra’s iconic voice, ensures that “That’s Life” continues to inspire and uplift, embodying the timeless spirit of overcoming and enduring, no matter what life throws our way.
2. New York, New York
“New York, New York” is an exuberant anthem that pays tribute to the vibrant spirit and relentless ambition of New York City, famously brought to life by Frank Sinatra’s iconic rendition. Written by John Kander and Fred Ebb for the 1977 Martin Scorsese film of the same name, the song didn’t achieve legendary status until Sinatra made it his own in 1979.
Sinatra’s version of “New York, New York” quickly outshone the original, becoming not only synonymous with the singer himself but also an unofficial anthem for the city it celebrates. The song’s lively tempo, grand orchestration, and Sinatra’s masterful vocal performance capture the essence of the city’s grandeur and the dreams it represents.
The lyrics, “Start spreading the news, I’m leaving today. I want to be a part of it, New York, New York,” invite listeners into a narrative of aspiration and determination. The song resonates with the city’s reputation as a land of opportunity, where ambition meets the promise of making it big.
Sinatra’s rendition of “New York, New York” is not just a song but a powerful cultural emblem, encapsulating the allure and dynamic rhythm of the city. It’s a musical celebration of New York’s indomitable spirit, its challenges and triumphs, and its role as a beacon for dreamers and doers alike. With its timeless appeal, the song continues to inspire and uplift, echoing the heartbeat of the city that never sleeps.
3. Fly Me To The Moon
“Fly Me to the Moon,” originally titled “In Other Words,” is a classic song that became inextricably linked to Frank Sinatra, especially after his 1964 recording with the Count Basie Orchestra, arranged by Quincy Jones. Written in 1954 by Bart Howard, the song underwent a transformation from a modest hit into a jazz standard, thanks in large part to Sinatra’s definitive and enchanting rendition.
The song’s romantic lyrics invite listeners on a celestial journey, offering a whimsical escape to the moon as a metaphor for the heights of love and aspiration. Sinatra’s smooth, controlled delivery perfectly complements the song’s gentle melody and the lush, sophisticated arrangements that accompany it. His interpretation adds a layer of depth and charm, turning the song into an intimate serenade that resonates with listeners’ deepest romantic yearnings.
“Fly Me to the Moon” gained further prominence when it was played on the Apollo 10 mission to orbit the moon, symbolically tying the song to the awe-inspiring realms of space exploration and human achievement. Sinatra’s version, in particular, has stood the test of time, enchanting generations with its dreamy allure and the timeless quality of his voice.
The song’s enduring popularity is a testament to its universal appeal, the artistry of Frank Sinatra, and the song’s ability to transport listeners beyond the ordinary, offering a glimpse of the sublime in the everyday. “Fly Me to the Moon” remains a quintessential piece of the Great American Songbook, and Sinatra’s rendition is often considered the definitive interpretation, immortalizing the tune in the hearts of music lovers around the world.
4. Strangers In The Night
“Strangers in the Night” is a famous song best known for Frank Sinatra’s 1966 version. The song was composed by Bert Kaempfert with English lyrics by Charles Singleton and Eddie Snyder. Sinatra’s rendition of the song was immensely successful and is considered one of his signature tunes.
The song is characterized by its smooth melody and romantic lyrics, which tell the story of two strangers who meet and fall in love. The phrase “Strangers in the Night” itself has become synonymous with the idea of unexpected encounters leading to romance. Sinatra’s version of the song won the Grammy Award for Record of the Year and Best Male Pop Vocal Performance. The song’s success marked a significant point in Sinatra’s career, contributing to his enduring popularity as one of the most iconic singers of the 20th century.
5. My Way
“My Way” is another iconic song famously performed by Frank Sinatra, though it was not originally written by him. The music was composed by Claude François and Jacques Revaux and originally titled “Comme d’habitude” (As Usual) in French. The English lyrics were written by Paul Anka after he heard the original French song.
Anka wrote these lyrics specifically for Sinatra, and the song was released in 1969. It quickly became a signature song for Sinatra, encapsulating his life, career, and attitude towards both. The lyrics convey a narrative of retrospection and self-reflection, with the protagonist looking back on his life and stating that he lived it “my way.”
“My Way” is known for its bold and empowering message of individualism and self-determination. It’s been covered by many other artists and remains a popular song for significant occasions and tributes. Sinatra’s version is particularly celebrated for its profound emotional delivery and orchestral arrangement, making it an enduring classic in the world of music.
6. I’ve Got You Under My Skin
“I’ve Got You Under My Skin” is a deeply evocative and enduring standard, immortalized by Frank Sinatra’s compelling renditions. Originally penned by Cole Porter in 1936 for the musical “Born to Dance,” the song became one of Sinatra’s signature tunes, especially after his 1956 version arranged by Nelson Riddle for the album “Songs for Swingin’ Lovers!”
Sinatra’s interpretation of “I’ve Got You Under My Skin” is a masterclass in vocal control, phrasing, and emotional depth. The song begins with a gentle, persuasive croon, gradually building into a passionate, full-throated declaration of love and obsession. The lyrics speak to the inescapable allure of a deep, consuming love, one that gets under the skin and takes hold of the heart irresistibly.
Nelson Riddle’s arrangement complements Sinatra’s vocal prowess with a lush orchestral background, punctuated by a bold, brassy crescendo, leading to an unforgettable trombone solo by Milt Bernhart. This musical interlude adds a dramatic flair, intensifying the song’s emotional impact.
“I’ve Got You Under My Skin” stands as a testament to Sinatra’s ability to imbue a song with nuanced emotion, transforming it into a personal and profound experience for the listener. The song remains a beloved classic, a highlight of the Great American Songbook, and one of the finest examples of Sinatra’s legendary artistry and his enduring collaboration with Nelson Riddle.
7. The Way You Look Tonight
“The Way You Look Tonight” is a classic song from the Great American Songbook, originally written for the film “Swing Time” in 1936. The music was composed by Jerome Kern, with lyrics by Dorothy Fields. The song was performed in the film by Fred Astaire and won the Academy Award for Best Original Song.
The song’s lyrics praise the beauty of the singer’s love interest, highlighting the enchantment and affection he feels when looking at her. Its tender melody and romantic lyrics have made it a favorite for decades, often associated with love and nostalgia.
Over the years, “The Way You Look Tonight” has been covered by numerous artists, including Frank Sinatra, whose version is particularly renowned. Sinatra’s rendition brought a new level of sophistication and emotion to the song, making it a staple at romantic events like weddings and anniversaries. The song’s timeless appeal lies in its ability to evoke deep emotions and memories, ensuring its place in the hearts of listeners across generations.
8. Summer Wind
“Summer Wind” is a warm, nostalgia-tinged song that became one of Frank Sinatra’s most beloved and enduring hits. Originally a German song titled “Der Sommerwind,” written by Heinz Meier with lyrics by Hans Bradtke, it was adapted into English by Johnny Mercer and given a new life through Sinatra’s evocative interpretation.
Recorded in 1966 and featured on the album “Strangers in the Night,” “Summer Wind” is a poignant reflection on the fleeting nature of love and time, likened to the gentle, transient breezes of summer. Sinatra’s rendition stands out for its understated elegance and the wistful longing in his voice, which perfectly captures the song’s reflective mood.
The arrangement complements Sinatra’s vocal delivery with a smooth, laid-back orchestration, setting the stage for a nostalgic journey. The lyrics paint vivid images of lost love and the passing of time, with the summer wind moving through the narrative as a metaphor for change and the impermanence of life’s moments.
“Summer Wind” endures as a classic in Sinatra’s repertoire, showcasing his ability to convey deep emotion and storytelling through song. Its timeless appeal lies in the universal experiences it touches — the bittersweet memory of past loves and the relentless march of time, all set against the backdrop of a soft, fading summer breeze.
9. I’ve Got The World On A String
“I’ve Got the World on a String” is a classic pop standard, with music composed by Harold Arlen and lyrics by Ted Koehler. The song was introduced in the 1932 revue “Nine-Fifteen Revue,” performed by Cab Calloway. However, it’s Frank Sinatra’s 1953 version, arranged by Nelson Riddle, that significantly contributed to the song’s enduring popularity.
In this upbeat and optimistic song, the lyrics express a sense of triumph and joy, with the singer declaring that they have control over their life and destiny, symbolized by having “the world on a string.” The imagery of holding the world like a balloon on a string suggests a feeling of elation and confidence.
Sinatra’s version of “I’ve Got the World on a String” is noted for its lively tempo, brassy arrangement, and Sinatra’s confident, swaggering vocal performance. It’s considered one of the songs that marked Sinatra’s comeback in the early 1950s, showcasing his ability to imbue songs with his unique style and charisma. The song has been covered by many artists over the years, but Sinatra’s rendition remains one of the most celebrated and iconic interpretations.
10. My Kind Of Town
“My Kind of Town (Chicago Is)” is another celebrated song closely associated with Frank Sinatra. The song was originally composed for the 1964 musical film “Robin and the 7 Hoods,” starring Sinatra along with Dean Martin, Sammy Davis Jr., and Bing Crosby. The music was composed by Jimmy Van Heusen, with lyrics by Sammy Cahn.
In the film, Sinatra’s character sings the song as a tribute to the city of Chicago, highlighting its vibrant culture and spirited people. The lyrics express a deep affection for the city, with Sinatra’s character declaring that Chicago is “my kind of town” and that it “has all that jazz.”
The song was nominated for the Academy Award for Best Original Song, and Sinatra’s rendition quickly became one of his signature tunes. His performance captures a sense of pride and love for Chicago, characterized by his smooth vocal style and the lively, brassy arrangement of the song.
“My Kind of Town” is notable for its catchy melody and upbeat, swinging rhythm, making it a staple in Sinatra’s concert repertoire and a favorite among his fans. The song remains a popular anthem for the city of Chicago and is often associated with Sinatra’s larger-than-life persona and his ability to bring the spirit of a city to life through music.
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.
