Frank Sinatra, also known as “The Voice,” was one of the most influential and successful musical artists of the 20th century. With a career spanning over six decades, Sinatra left a lasting impact on the music industry and his fans with his smooth vocals and charming personality. Known for his interpretation of standards and ballads, he became an icon in American music, winning numerous awards and accolades throughout his career.
In this list, we’ll explore the 10 best Frank Sinatra songs of all time, showcasing his diverse range of musical styles and unforgettable performances. From his signature songs like “My Way” and “New York, New York” to lesser-known gems like “It Was a Very Good Year,” these songs continue to inspire and entertain audiences today.
1. My Way
“My Way” is a song by Frank Sinatra that was released in 1969. The song has become one of Sinatra’s most popular and iconic songs, known for its powerful and emotional lyrics. The song was originally composed by French songwriter Jacques Revaux, but it was the English lyrics written by Paul Anka that helped turn it into a classic. “My Way” is a song about living life on one’s own terms and making choices that are true to oneself. Sinatra’s masterful vocals convey the sense of pride and determination that the song celebrates, making it a timeless classic that has resonated with audiences for generations.
2. Fly Me to the Moon
“Fly Me to the Moon” is a classic song by Frank Sinatra that was released in 1964. The song, originally titled “In Other Words,” was written by Bart Howard in 1954. The song’s upbeat tempo and smooth lyrics make it an all-time favorite of Sinatra’s fans. The song has been featured in several movies and TV shows and has been covered by numerous artists over the years. Sinatra’s interpretation of “Fly Me to the Moon” has become synonymous with the American popular songbook, and it remains one of his most iconic and beloved songs.
3. New York, New York
“New York, New York” is a classic Frank Sinatra song that has become synonymous with the city it describes. Written by John Kander and Fred Ebb, the song was originally recorded for the 1977 Martin Scorsese film of the same name. The lyrics are a celebration of New York City, with its bright lights, bustling streets, and endless opportunities. Sinatra’s smooth and confident vocals perfectly capture the energy of the city, making the song a beloved anthem for New Yorkers and tourists alike.
4. Strangers in the Night
“Strangers in the Night” is a popular song that was recorded by Frank Sinatra in 1966. The song has a catchy melody and a memorable trumpet solo that opens and closes the song. The lyrics tell the story of two strangers who meet by chance and fall in love. The song was a huge commercial success, reaching number one on the Billboard Hot 100 chart and earning Sinatra a Grammy Award for Best Male Pop Vocal Performance.
5. Come Fly with Me
“Come Fly with Me” is a classic Frank Sinatra song that embodies the glamorous spirit of the jet-setting era. It was released in 1958 as the title track of his album, “Come Fly with Me”. The song opens with a buoyant trumpet melody that evokes the excitement of travel, and Sinatra’s smooth vocals invite the listener to join him on an adventure. The lyrics paint a picture of exotic locales and romantic encounters, and the upbeat tempo and swing rhythm make it impossible not to tap your feet and feel the urge to dance.
6. The Way You Look Tonight
The Way You Look Tonight” is a classic love song by Frank Sinatra that was written by Jerome Kern and Dorothy Fields for the film “Swing Time” in 1936. Sinatra’s version was released in 1964 and became a hit, earning him a Grammy Award for Best Vocal Performance, Male. The song is known for its romantic and nostalgic lyrics, with Sinatra crooning about how the person he loves looks so beautiful and how he can’t help but feel happy when he’s with them. The melody is simple and sweet, featuring a slow swing tempo with gentle piano and strings accompaniment that perfectly complements Sinatra’s smooth vocals.
7. I’ve Got You Under My Skin
“I’ve Got You Under My Skin” is a classic song recorded by Frank Sinatra in 1956. Written by Cole Porter, the song has become one of Sinatra’s signature tunes and is considered a standard of the American songbook. The song features a memorable opening instrumental section and Sinatra’s smooth vocals that build in intensity as the song progresses. The lyrics describe a love that has become so deeply ingrained that it feels like it’s under the skin, and Sinatra’s interpretation captures the passion and intensity of the emotions involved.
8. That’s Life
“That’s Life” is a classic Frank Sinatra song that was released in 1966. The song was written by Dean Kay and Kelly Gordon and quickly became a favorite among Sinatra’s fans. The song’s lyrics talk about the ups and downs of life and how one must accept the good with the bad. Sinatra’s signature smooth voice shines through in this song, which is accompanied by an upbeat and catchy melody. “That’s Life” became one of Sinatra’s most popular songs and has been covered by many artists over the years. Its timeless message and infectious rhythm continue to captivate listeners to this day.
9. Night and Day
“Night and Day” is a classic song by Frank Sinatra, originally composed by Cole Porter for the 1932 musical play “Gay Divorce.” Sinatra’s version, released in 1942, is a timeless rendition that showcases his smooth and sultry vocal style. The song’s lush orchestration and melodic phrasing create a romantic and dreamy atmosphere, perfectly capturing the essence of Porter’s lyrics. The song has become a standard in the Great American Songbook and has been covered by numerous artists over the years, but Sinatra’s version remains one of the most iconic and memorable.
10. It Was a Very Good Year
“It Was a Very Good Year” is a classic Frank Sinatra song that was released in 1965. The song features a reflective and nostalgic tone and describes the various stages of life and the memories that come with them. The lyrics take the listener through the experiences of a man at different ages, starting from the time when he was 17 to his later years when he’s in his twilight years. Sinatra’s vocal performance on the song is masterful, capturing the wistful and contemplative mood of the lyrics perfectly.