Frank Sinatra, born Francis Albert Sinatra on December 12, 1915, in Hoboken, New Jersey, was an American singer, actor, and producer who was one of the most popular and influential musical artists of the 20th century. Known for his smooth voice and impeccable phrasing, Sinatra was a pioneer of the concept album and was known for his interpretations of the Great American Songbook. He rose to fame in the 1940s as a solo artist and became a leading actor in Hollywood, winning an Academy Award for Best Supporting Actor for his role in “From Here to Eternity” in 1953. Sinatra continued to perform and record music until his death in 1998, leaving behind a rich legacy of music and film.
1. My Way
“My Way” is a song closely associated with Frank Sinatra, although it was originally a French song called “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.
Sinatra’s version of “My Way” was released in 1969 on his album of the same name. The song became one of Sinatra’s signature songs, often considered an anthem of individualism and self-belief. Its lyrics reflect on a person’s life journey, expressing a sense of pride in having lived life on one’s own terms, despite its ups and downs. “My Way” is widely regarded as one of Sinatra’s greatest recordings and remains a popular and enduring classic.
2. Fly Me to the Moon
“Fly Me to the Moon” is a timeless classic performed by Frank Sinatra. Released in 1964 on his album *It Might as Well Be Swing*, the song has become one of Sinatra’s signature tunes. Written by Bart Howard, the song’s lyrics express a longing for adventure and romance, with the narrator inviting their lover to join them on a journey to the moon and beyond. Sinatra’s smooth, velvety voice, accompanied by lush orchestration, brings the song to life, capturing the imagination and stirring the hearts of listeners. “Fly Me to the Moon” has since become a standard in the Great American Songbook, enduring through generations as a symbol of love and aspiration.
3. I’ve Got You Under My Skin
“I’ve Got You Under My Skin” is a classic song performed by Frank Sinatra, composed by Cole Porter. It was written in 1936 for the musical “Born to Dance” and has since become a jazz standard, with Sinatra’s rendition being one of the most famous.
Sinatra’s recording of “I’ve Got You Under My Skin” was released in 1956 on his album “Songs for Swingin’ Lovers!” The song features a lush orchestral arrangement and Sinatra’s smooth, emotive vocals. The lyrics describe the experience of being deeply in love and unable to shake thoughts of the beloved.
Sinatra’s interpretation of “I’ve Got You Under My Skin” is celebrated for its passionate delivery and impeccable phrasing, showcasing his vocal prowess and emotional depth. The song remains a beloved classic in the Great American Songbook.
4. Strangers in the Night
“Strangers in the Night” is a timeless classic performed by Frank Sinatra, released in 1966 as a single and later included on his album of the same name. Written by Bert Kaempfert, Charles Singleton, and Eddie Snyder, the song tells the story of two strangers who share a brief encounter that sparks a romantic connection. Sinatra’s smooth vocals, combined with the song’s lush orchestration and memorable melody, create a captivating and nostalgic atmosphere. “Strangers in the Night” became one of Sinatra’s biggest hits, topping the charts worldwide and earning him a Grammy Award for Record of the Year. It remains an iconic song in Sinatra’s repertoire and a beloved standard in the Great American Songbook.
5. The Way You Look Tonight
“The Way You Look Tonight” is a classic song 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 won the Academy Award for Best Original Song that year.
Frank Sinatra recorded “The Way You Look Tonight” multiple times throughout his career, with one of the most notable versions appearing on his 1964 album “Sinatra Sings Days of Wine and Roses, Moon River, and Other Academy Award Winners.” Sinatra’s rendition of the song is characterized by his smooth vocals and the elegant orchestral arrangement.
“The Way You Look Tonight” is a timeless ballad that has been covered by numerous artists over the years. It is celebrated for its romantic lyrics and beautiful melody, making it a popular choice for weddings and romantic occasions.
6. That’s Life
“That’s Life” is a classic song famously performed by Frank Sinatra. Released in 1966 on his album of the same name, the song was written by Dean Kay and Kelly Gordon. It features a vibrant big band arrangement and Sinatra’s trademark smooth vocals. The lyrics reflect on life’s ups and downs, with the narrator expressing resilience and determination in the face of adversity. “That’s Life” became one of Sinatra’s signature songs, resonating with audiences for its relatable message and spirited delivery. It has since become a timeless anthem of perseverance, inspiring listeners to embrace life’s challenges with courage and optimism.
7. Come Fly with Me
“Come Fly with Me” is a classic song performed by Frank Sinatra, composed by Jimmy Van Heusen with lyrics by Sammy Cahn. It was first recorded by Sinatra in 1957 for his album of the same name.
The song’s lyrics invite the listener to embark on a journey of adventure and romance, with lines like “Come fly with me, let’s fly, let’s fly away” evoking a sense of freedom and excitement. The upbeat tempo and swinging arrangement, featuring a big band and orchestra, contribute to the song’s lively and infectious energy.
“Come Fly with Me” has since become one of Sinatra’s signature songs, emblematic of his style and charisma as a performer. It is regarded as a classic in the Great American Songbook and remains a popular standard in jazz and pop music.
8. One for My Baby (And One More for the Road)
“One for My Baby (And One More for the Road)” is a poignant ballad famously performed by Frank Sinatra. Written by Harold Arlen and Johnny Mercer, the song was first introduced in the 1943 musical *The Sky’s the Limit*. Sinatra’s rendition, released in 1958 on his album *Frank Sinatra Sings for Only the Lonely*, is considered definitive.
The song features a melancholic atmosphere, with Sinatra portraying a character who seeks solace in a bar after experiencing heartache. The lyrics depict a conversation between the narrator and the bartender, where the narrator laments lost love and requests “one for my baby” as he tries to numb the pain. The song’s evocative melody, Sinatra’s emotive delivery, and Nelson Riddle’s lush orchestration combine to create a deeply affecting and timeless masterpiece. “One for My Baby” has since become a quintessential standard in the Great American Songbook, revered for its emotional depth and Sinatra’s unparalleled interpretation.
9. Witchcraft
“Witchcraft” is a classic song popularized by Frank Sinatra, written by Cy Coleman and Carolyn Leigh. It was first recorded by Sinatra in 1957 for his album “Sinatra’s Sinatra,” a collection of re-recorded versions of his earlier hits.
The song’s lyrics use the metaphor of “witchcraft” to describe the feeling of being irresistibly drawn to someone. Lines like “Those fingers in my hair, that sly come-hither stare” convey a sense of enchantment and allure. The song’s sophisticated melody and arrangement, featuring a lush orchestral accompaniment, complement Sinatra’s smooth vocals.
“Witchcraft” became one of Sinatra’s signature songs and remains a beloved classic in the Great American Songbook. It has been covered by many artists over the years and is celebrated for its timeless appeal and romantic lyrics.
10. Summer Wind
“Summer Wind” is a classic song performed by Frank Sinatra, originally released in 1966 on his album *Strangers in the Night*. Written by Johnny Mercer and Hans Bradtke with music by Heinz Meier, the song captures the essence of fleeting summer romance.
Sinatra’s smooth vocals, accompanied by a lush orchestral arrangement, evoke the carefree spirit of summer as the lyrics reminisce about a past love affair that occurred during the warm summer months. The song’s wistful melody and nostalgic lyrics paint a vivid picture of lazy summer days and balmy evenings spent in the embrace of love.
“Summer Wind” has become one of Sinatra’s most beloved and enduring songs, embodying the sentimentality and romance of the Great American Songbook. Its timeless appeal continues to captivate listeners, transporting them to a bygone era of romance and nostalgia with each listen.