Frank Sinatra, born Francis Albert Sinatra (December 12, 1915 – May 14, 1998), was an American singer, actor, and producer who remains one of the most iconic and influential figures in the history of popular music. Often referred to as “Ol’ Blue Eyes,” Sinatra’s career spanned over six decades, during which he achieved remarkable success in various facets of the entertainment industry.
Sinatra’s distinctive voice, impeccable phrasing, and emotive delivery captivated audiences worldwide. He was known for his versatility, effortlessly transitioning between genres such as traditional pop, jazz, swing, and even rock and roll. Sinatra’s discography includes numerous timeless classics, including “My Way,” “Fly Me to the Moon,” “New York, New York,” and “Strangers in the Night,” among many others.
In addition to his music career, Sinatra found success as a film actor, starring in over 60 movies and winning an Academy Award for Best Supporting Actor for his role in “From Here to Eternity” (1953). He also made significant contributions to television, hosting and appearing in several popular variety shows and specials.
Sinatra’s influence extended beyond his music and acting careers. He was a cultural icon and a symbol of style and sophistication, known for his impeccable fashion sense and charismatic persona. His impact on popular culture is immeasurable, and his legacy continues to be celebrated by fans and artists alike.
Throughout his life, Sinatra received numerous awards and honors, including multiple Grammy Awards, an Academy Award, and the Presidential Medal of Freedom. He remains one of the best-selling music artists of all time, with an enduring legacy that continues to inspire and resonate with audiences around the world.
1. My Way
“My Way” is a timeless classic originally popularized by Frank Sinatra, released in 1969. The song’s lyrics were penned by Paul Anka, based on a French song called “Comme d’habitude” (“As Usual”) by Claude François and Jacques Revaux.
“My Way” is renowned for its poignant and introspective lyrics, which reflect on the journey of life and the pursuit of one’s dreams and aspirations. The song’s narrator expresses pride in their choices and actions, acknowledging both triumphs and failures, but ultimately asserting their individuality and self-determination.
Frank Sinatra’s rendition of “My Way” became one of his signature songs, capturing the essence of his persona as the epitome of sophistication and self-assurance. His smooth and emotive delivery, paired with a lush orchestral arrangement, elevated the song to iconic status.
Over the years, “My Way” has been covered by numerous artists from various genres, cementing its status as a timeless classic. Its universal themes of resilience, self-discovery, and the pursuit of personal fulfillment continue to resonate with audiences around the world, making it one of the most beloved and enduring songs in the American songbook.
2. Fly Me to the Moon
“Fly Me to the Moon” is a classic jazz standard written by Bart Howard in 1954. The song has been performed by numerous artists over the years, but it was popularized by Frank Sinatra, who recorded a memorable version in 1964 for his album “It Might as Well Be Swing.”
“Fly Me to the Moon” is known for its romantic lyrics and dreamy melody, evoking the feelings of love and longing. The song’s narrator expresses a desire to escape with their loved one and journey to the moon, using the imagery of space travel to convey the depth of their affection.
Sinatra’s rendition of “Fly Me to the Moon” is considered one of his signature songs, featuring his smooth vocals and impeccable phrasing. The arrangement, conducted by Quincy Jones, includes lush orchestration and a swinging rhythm section, adding to the song’s charm and elegance.
Over the years, “Fly Me to the Moon” has become a jazz standard, performed by countless artists in various styles and genres. Its timeless appeal and universal themes of romance and adventure continue to captivate listeners, making it one of the most beloved songs in the Great American Songbook.
3. New York, New York
“New York, New York” is a song originally performed by Liza Minnelli in the 1977 Martin Scorsese film “New York, New York.” However, the version most commonly associated with the title is the rendition by Frank Sinatra.
Sinatra’s version of “New York, New York” was recorded in 1979 and released as a single in 1980. It became one of his signature songs and an anthem for the city of New York. The song’s lyrics celebrate the city’s energy, glamour, and allure, while also acknowledging its challenges and hardships. The chorus, with its famous refrain “Start spreading the news, I’m leaving today,” has become iconic and synonymous with the city itself.
“New York, New York” is often played at events and celebrations in New York City, including sporting events and New Year’s Eve celebrations in Times Square. It has also been featured in numerous films, television shows, and commercials, further solidifying its status as a cultural touchstone.
Sinatra’s version of “New York, New York” remains a beloved classic and is widely regarded as one of the greatest songs about the city. It continues to evoke the spirit and essence of New York for listeners around the world.
4. Strangers in the Night
“Strangers in the Night” is a popular song written by Bert Kaempfert, with lyrics by Charles Singleton and Eddie Snyder. It was first performed by Frank Sinatra and released as a single in 1966. The song was included on Sinatra’s album of the same name, which was released in 1966.
“Strangers in the Night” became one of Sinatra’s most famous and enduring songs, reaching the top of the charts in multiple countries, including the United States and the United Kingdom. It won the Grammy Award for Record of the Year and Best Male Pop Vocal Performance in 1967.
The song is characterized by its lush orchestration, memorable melody, and Sinatra’s smooth vocal delivery. The lyrics tell the story of two strangers who meet by chance and share a romantic encounter, capturing the sense of mystery and excitement that can come with unexpected connections.
“Strangers in the Night” has been covered by numerous artists and has been featured in various films, television shows, and commercials over the years. It remains a classic of popular music and is often regarded as one of Sinatra’s signature songs.
5. That’s Life
“That’s Life” is a classic song made famous by Frank Sinatra, released in 1966 as the title track of his album “That’s Life.” Written by Dean Kay and Kelly Gordon, the song is renowned for its upbeat tempo, catchy melody, and resilient lyrics.
In “That’s Life,” the narrator reflects on the ups and downs of life, acknowledging the challenges and setbacks they have faced. Despite the setbacks, the song’s protagonist remains optimistic and resilient, asserting their determination to keep moving forward and embracing life’s highs and lows.
Frank Sinatra’s rendition of “That’s Life” is characterized by his trademark smooth vocals and dynamic delivery, capturing the spirit of resilience and perseverance. The song’s triumphant chorus, with its memorable refrain “That’s life (that’s life), that’s what all the people say,” has become synonymous with Sinatra’s enduring appeal and charisma.
“That’s Life” has since become a classic anthem of resilience and determination, inspiring listeners to embrace life’s challenges with courage and fortitude. It continues to be celebrated as one of Sinatra’s most iconic and enduring songs, resonating with audiences of all ages with its timeless message of hope and resilience.
6. I’ve Got You Under My Skin
“I’ve Got You Under My Skin” is a classic song written by Cole Porter in 1936. It was first introduced in the musical “Born to Dance” by Eleanor Powell and James Stewart. However, the song gained widespread recognition after being popularized by Frank Sinatra.
Sinatra’s rendition of “I’ve Got You Under My Skin” was recorded in 1956 for his album “Songs for Swingin’ Lovers!” His version is considered one of the definitive interpretations of the song. Sinatra’s smooth and emotive delivery, coupled with Nelson Riddle’s lush orchestration, contributed to the song’s enduring popularity.
“I’ve Got You Under My Skin” is a romantic ballad that describes the intense feelings of infatuation and longing experienced by the narrator. The lyrics convey the idea of being deeply captivated by someone to the point where they feel like they are under the narrator’s skin.
The song has been covered by numerous artists over the years and has been featured in various films, television shows, and commercials. It remains a beloved classic in the Great American Songbook and is often regarded as one of Sinatra’s greatest performances.
7. The Way You Look Tonight
“The Way You Look Tonight” is a timeless jazz standard written by Jerome Kern, with lyrics by Dorothy Fields. It was originally featured in the 1936 film “Swing Time,” where it was performed by Fred Astaire. The song went on to win the Academy Award for Best Original Song that year.
“The Way You Look Tonight” is a romantic ballad that expresses admiration and affection for a loved one. The lyrics celebrate the beauty and charm of the person being addressed, with imagery that evokes elegance and grace. The song’s melody is lush and melodic, with a timeless quality that has made it a favorite for weddings, dances, and romantic occasions.
Over the years, “The Way You Look Tonight” has been covered by numerous artists from various genres, including Frank Sinatra, Tony Bennett, and Michael Bublé, among others. Sinatra’s rendition, in particular, became one of his signature songs and remains one of the most iconic interpretations of the classic.
“The Way You Look Tonight” has endured as a beloved standard in the Great American Songbook, cherished for its timeless melody, heartfelt lyrics, and romantic sentiment. It continues to captivate listeners with its timeless elegance and remains a quintessential song for celebrating love and romance.
8. Come Fly With Me
“Come Fly with Me” is a classic song written by Jimmy Van Heusen, with lyrics by Sammy Cahn. It was composed in 1957 for the concept album of the same name, performed by Frank Sinatra.
“Come Fly with Me” is one of Sinatra’s signature songs and is characterized by its upbeat tempo, swinging rhythm, and evocative lyrics. The song invites the listener to embark on a romantic adventure, suggesting traveling to exotic destinations and experiencing the wonders of the world together.
Sinatra’s smooth vocal delivery and Nelson Riddle’s dynamic orchestration contribute to the song’s timeless appeal. “Come Fly with Me” captures the optimism and excitement of travel and romance, making it a favorite among fans of the Great American Songbook.
The song has been covered by numerous artists over the years and has been featured in various films, television shows, and commercials. It remains a classic of popular music and is often regarded as one of Sinatra’s greatest recordings.
9. Summer Wind
“Summer Wind” is a classic song originally written in German as “Der Sommerwind” by Heinz Meier, with English lyrics by Johnny Mercer. The English version was popularized by Frank Sinatra in 1966 on his album “Strangers in the Night.”
“Summer Wind” is a nostalgic and romantic ballad that evokes the feelings of warmth and nostalgia associated with the summer season. The song’s narrator reminisces about a past love affair that blossomed during the summer months, with lyrics that paint vivid imagery of carefree days and breezy nights.
Sinatra’s rendition of “Summer Wind” is characterized by his smooth vocals and impeccable phrasing, capturing the song’s wistful and sentimental mood. The arrangement features lush orchestration, including sweeping strings and gentle percussion, adding to the song’s evocative atmosphere.
“Summer Wind” has since become a beloved classic, covered by numerous artists in various genres. Its timeless appeal and romantic sentiment continue to resonate with audiences, making it a perennial favorite for lovers of jazz and easy listening music.
10. One for My Baby (And One More for the Road)
“One for My Baby (And One More for the Road)” is a classic song written by Harold Arlen, with lyrics by Johnny Mercer. It was composed in 1943 for the musical “The Sky’s the Limit,” where it was introduced by Fred Astaire.
The song is a poignant and melancholic ballad, often performed as a torch song. It features a narrator who finds solace in a bar late at night, pouring out their troubles to the bartender. The lyrics convey a sense of loneliness and heartache, with the narrator seeking comfort in alcohol as they cope with a failed relationship.
“One for My Baby (And One More for the Road)” has been recorded by numerous artists over the years, but it is perhaps most closely associated with Frank Sinatra. Sinatra’s rendition, recorded in 1958 for his album “Frank Sinatra Sings for Only the Lonely,” is widely regarded as one of the definitive interpretations of the song.
Sinatra’s emotive vocal delivery and Nelson Riddle’s lush orchestration contribute to the song’s emotional impact. “One for My Baby (And One More for the Road)” remains a beloved classic in the Great American Songbook and is often regarded as one of Sinatra’s greatest performances.
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.
