Frank Sinatra, born Francis Albert Sinatra on December 12, 1915, was an American singer, actor, and producer who was one of the most popular and influential musical artists of the 20th century. Often referred to as “Ol’ Blue Eyes,” Sinatra is widely regarded as one of the greatest vocalists of all time.
Sinatra’s career spanned over six decades, during which he achieved both critical acclaim and commercial success. He rose to fame in the 1940s as a solo artist, with hits like “All or Nothing at All,” “I’ll Never Smile Again,” and “I’ve Got You Under My Skin.” His smooth and emotive singing style, along with his impeccable phrasing and timing, captivated audiences and earned him a loyal following.
In addition to his musical career, Sinatra also achieved success as an actor, starring in numerous films throughout the 1940s, ’50s, and ’60s. Some of his most notable film roles include “From Here to Eternity” (1953), for which he won the Academy Award for Best Supporting Actor, “The Man with the Golden Arm” (1955), and “The Manchurian Candidate” (1962).
Sinatra’s influence extended beyond music and film; he was also a prominent figure in American popular culture and politics. He was known for his charisma, charm, and larger-than-life persona, and he was often seen socializing with celebrities, politicians, and other influential figures.
Throughout his career, Sinatra won numerous awards, including 11 Grammy Awards and three Academy Awards. He was inducted into the Grammy Hall of Fame, the Songwriters Hall of Fame, and the Hollywood Walk of Fame, among others.
Sinatra continued to perform and record music well into his later years, remaining active in the entertainment industry until his death on May 14, 1998. His legacy as a cultural icon and musical legend continues to endure, with his songs remaining popular and influential to this day.
1. My Way
“My Way” is a song popularized by Frank Sinatra, although it was originally a French song titled “Comme d’habitude” (“As Usual”), with music by Claude François and Jacques Revaux and lyrics by Claude François and Gilles Thibault. The English lyrics for “My Way” were written by Paul Anka, based on the original French version.
Frank Sinatra’s rendition of “My Way” became one of his signature songs and remains one of the most iconic and enduring songs in his vast repertoire. Released in 1969 on his album of the same name, “My Way” quickly became a classic and is often associated with Sinatra’s persona and legacy.
The lyrics of “My Way” reflect on a life lived with independence, self-assurance, and resilience. The narrator reflects on the ups and downs of life, expressing pride in having lived life on their own terms, with no regrets. The song’s powerful message of self-determination and resilience has resonated with audiences around the world.
“My Way” has been covered by numerous artists across various genres and languages, but Sinatra’s version remains the most famous and beloved. It has been used in numerous films, TV shows, and commercials, and it continues to be a popular choice for events and celebrations.
The song’s timeless appeal and universal themes have made it a cultural touchstone and a defining anthem for generations. “My Way” remains a fitting tribute to Frank Sinatra’s legendary career and enduring legacy as one of the greatest entertainers of all time.
2. Fly Me to the Moon
“Fly Me to the Moon” is a classic song written by Bart Howard in 1954. Originally titled “In Other Words,” it became popularized under its new name when Frank Sinatra recorded a version of it in 1964. Sinatra’s rendition is the most well-known and frequently played, although the song has been covered by numerous artists over the years.
“Fly Me to the Moon” is a romantic ballad that expresses a desire for adventure and exploration, using imagery of space travel to convey the longing to be with a loved one. The lyrics invite the listener to take a journey to the moon and back, symbolizing the depth of affection and devotion.
Sinatra’s recording of “Fly Me to the Moon” is characterized by his smooth, velvety voice and the lush orchestration that accompanies it. His interpretation of the song captures the elegance and sophistication of the era in which it was recorded, making it a timeless classic.
“Fly Me to the Moon” has since become one of Sinatra’s signature songs and remains a popular choice for weddings, romantic occasions, and celebrations of all kinds. Its enduring popularity and universal appeal have cemented its status as one of the greatest love songs of all time.
3. New York, New York
“New York, New York” is a classic song famously performed by Frank Sinatra. It was written by John Kander and Fred Ebb for the Martin Scorsese-directed musical film “New York, New York” (1977), where it was originally performed by Liza Minnelli. However, it was Sinatra’s rendition that became the most well-known and enduring.
Sinatra’s version of “New York, New York” was recorded in 1979 and released as a single from his album “Trilogy: Past Present Future.” The song is characterized by its upbeat tempo, swinging rhythm, and iconic lyrics that celebrate the city of New York as a symbol of aspiration, resilience, and opportunity.
The song’s lyrics evoke the excitement and energy of New York City, capturing its vibrant atmosphere and bustling streets. The chorus, with its memorable refrain “New York, New York, it’s a helluva town,” has become synonymous with the city and is often played at events and celebrations in New York and beyond.
“New York, New York” has since become one of Sinatra’s signature songs and a beloved anthem for the city of New York. It has been covered by numerous artists and featured in various films, TV shows, and commercials, further solidifying its status as a timeless classic in the American songbook.
4. Strangers in the Night
“Strangers in the Night” is a classic song performed by Frank Sinatra, released in 1966. The song is characterized by its smooth melody, romantic lyrics, and Sinatra’s signature vocal style. “Strangers in the Night” tells the story of two strangers who meet by chance and share a fleeting romantic encounter. The song’s lyrics convey a sense of spontaneity and passion, capturing the excitement and uncertainty of a newfound romance. “Strangers in the Night” became one of Frank Sinatra’s biggest hits, reaching the top of the charts and winning the Grammy Award for Record of the Year in 1967. It remains a timeless classic and a favorite among fans of Sinatra and the Great American Songbook.
5. That’s Life
“That’s Life” is a classic song performed by Frank Sinatra. It was written by Dean Kay and Kelly Gordon and was released by Sinatra in 1966 on his album of the same name, “That’s Life.”
The song’s lyrics reflect on the ups and downs of life, acknowledging the setbacks and challenges that one may face but ultimately expressing resilience and determination to persevere. The narrator reflects on the unpredictability of life, with its highs and lows, and asserts that despite the setbacks, they will continue to move forward and embrace whatever comes their way.
Sinatra’s recording of “That’s Life” is characterized by his powerful and emotive vocal delivery, as well as the swinging arrangement that accompanies it. The song’s upbeat tempo and catchy melody make it a quintessential example of Sinatra’s style and charisma.
“That’s Life” has since become one of Sinatra’s signature songs and remains a favorite among fans of his music. It has been covered by numerous artists and featured in various films, TV shows, and commercials, further solidifying its status as a timeless classic in the American songbook.
6. I’ve Got You Under My Skin
“I’ve Got You Under My Skin” is a classic song famously performed by Frank Sinatra. It was written by Cole Porter in 1936 and has since become one of Porter’s most enduring compositions.
Sinatra’s rendition of “I’ve Got You Under My Skin” was recorded multiple times throughout his career, but the most famous version was released in 1956 on his album “Songs for Swingin’ Lovers!” The song features an arrangement by Nelson Riddle and his orchestra, and it showcases Sinatra’s smooth and emotive vocal delivery.
The lyrics of “I’ve Got You Under My Skin” describe the narrator’s infatuation with someone who has deeply affected them, to the point where they feel as though the person is “under their skin.” The song expresses the intensity of romantic desire and the inability to shake off the object of affection, despite knowing that it may not be wise.
Sinatra’s recording of “I’ve Got You Under My Skin” became a major hit and remains one of his signature songs. It has been covered by numerous artists over the years and has been featured in various films, TV shows, and commercials, solidifying its status as a timeless classic in the American songbook.
7. The Way You Look Tonight
“The Way You Look Tonight” is a classic song written by Jerome Kern and Dorothy Fields, originally performed by Fred Astaire in the 1936 film “Swing Time.” It’s a timeless jazz standard that has been covered by numerous artists over the years. The song is characterized by its elegant melody and romantic lyrics, which express admiration for the beauty and charm of a loved one. “The Way You Look Tonight” has become a beloved classic in the Great American Songbook, cherished for its heartfelt sentiment and enduring appeal. Frank Sinatra’s rendition of the song is particularly renowned, capturing the essence of romance and sophistication that the song embodies.
8. Come Fly With Me
“Come Fly with Me” is a classic song performed by Frank Sinatra. It was written by Jimmy Van Heusen and Sammy Cahn and was first recorded by Sinatra in 1957 for his album of the same name, “Come Fly with Me.”
The song’s lyrics invite the listener to embark on a romantic adventure and explore the world together. It captures the excitement and anticipation of travel, with references to exotic destinations and the promise of new experiences. The narrator encourages their companion to “come fly with me” and escape the mundane realities of everyday life.
Sinatra’s recording of “Come Fly with Me” features a swinging arrangement by Billy May and his orchestra, complete with brass flourishes and a catchy melody. His smooth and confident vocal delivery perfectly captures the sense of adventure and spontaneity conveyed in the lyrics.
“Come Fly with Me” became one of Sinatra’s signature songs and remains a beloved classic in his vast repertoire. It has been covered by numerous artists over the years and has been featured in various films, TV shows, and commercials, solidifying its status as a timeless standard in the American songbook.
9. Summer Wind
“Summer Wind” is a song originally written in German (“Der Sommerwind”) by Heinz Meier, with English lyrics by Johnny Mercer. It was first recorded by Wayne Newton in 1965. However, the most famous version is the one performed by Frank Sinatra, released in 1966 on his album “Strangers in the Night.”
“Summer Wind” is characterized by its breezy melody and nostalgic lyrics that evoke memories of summer romance and carefree days. The song tells the story of a fleeting summer romance that comes to an end with the changing seasons, leaving behind bittersweet memories of love and longing. Sinatra’s smooth vocals and impeccable phrasing perfectly capture the wistful sentiment of the song, making his rendition the definitive version for many listeners. “Summer Wind” has since become a classic of the Great American Songbook and remains a favorite among fans of Sinatra and timeless music alike.
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 performed by Frank Sinatra. It was written by Harold Arlen and Johnny Mercer and was first published in 1943.
The song is a poignant and melancholic ballad that tells the story of a man who finds himself alone in a bar late at night, lamenting the end of a relationship and drowning his sorrows in alcohol. The narrator engages in a conversation with the bartender, who serves as a sympathetic listener as he recounts his troubles and reflects on lost love.
The title of the song refers to the narrator’s ritual of ordering one last drink (“one for my baby”) before leaving the bar (“and one more for the road”). The lyrics capture the bittersweet emotions of heartbreak and loneliness, as well as the desire to numb the pain with alcohol.
Sinatra’s recording of “One for My Baby (And One More for the Road)” is widely regarded as one of his greatest performances. His emotive and soulful vocal delivery, combined with the sparse and haunting arrangement, perfectly captures the mood of the song and conveys the narrator’s sense of despair and resignation.
The song has since become a standard in the Great American Songbook and has been covered by numerous artists across different genres. It remains a timeless classic that continues to resonate with listeners, evoking feelings of longing, nostalgia, and empathy.