Frank Sinatra, also known as Ol’ Blue Eyes, is one of the most iconic and influential performers in American history. His career spanned several decades and he became known for his smooth voice, impeccable style, and charismatic personality. Sinatra’s music continues to be enjoyed by people of all ages, and his songs have become classics that are recognized all over the world.
In this article, we will be counting down the 10 best Frank Sinatra songs of all time. From his early days as a crooner in the 1940s to his later years as a mature and reflective artist, we will explore the songs that showcase Sinatra’s incredible talent and enduring legacy. Whether you are a lifelong fan or a newcomer to his music, this list will provide a comprehensive overview of the very best that Frank Sinatra has to offer. So sit back, relax, and let us take you on a journey through the music of one of the greatest singers of all time.
1. Fly Me To The Moon
“Fly Me to the Moon” is a timeless classic and one of Frank Sinatra’s most beloved songs. Originally titled “In Other Words,” the song was written in 1954 by Bart Howard and has since been covered by countless artists. Sinatra’s version, however, is perhaps the most famous and is widely considered to be the definitive interpretation of the song. With its upbeat tempo and romantic lyrics, “Fly Me to the Moon” captures the spirit of the space age and the optimism of the era in which it was written. Sinatra’s smooth, effortless vocals are perfectly suited to the song’s jazzy, swing-inspired arrangement, and the result is a masterpiece of popular music that continues to captivate audiences to this day.
2. My Way
“My Way” is an iconic ballad that was famously recorded by Frank Sinatra in 1969. Written by Paul Anka, the song is a powerful meditation on the value of self-determination and individualism. Sinatra’s version of “My Way” has become a cultural touchstone and is often played at important events such as graduations and funerals. The song’s emotional impact is largely due to Sinatra’s powerful vocals and his ability to infuse every line with a deep sense of conviction and personal meaning. The soaring orchestration of the song, which builds to a powerful crescendo in the final verse, adds to its dramatic impact. “My Way” is a timeless classic that continues to resonate with listeners of all ages and backgrounds, and its message of self-belief and perseverance remains as relevant today as it was over 50 years ago.
3. Summer Wind
“Summer Wind” is a romantic classic that was recorded by Frank Sinatra in 1966. The song was written by Johnny Mercer and Hans Bradtke and has since been covered by a number of other artists, but Sinatra’s version remains the most famous. With its gentle, breezy melody and evocative lyrics, “Summer Wind” perfectly captures the feeling of a lazy summer day. Sinatra’s rich, velvety voice is perfectly suited to the song’s romantic, wistful tone, and the result is a timeless classic that continues to enchant listeners to this day. The song’s lush, orchestral arrangement, featuring sweeping strings and jazzy horns, only adds to its timeless appeal. “Summer Wind” is a beautiful and evocative song that showcases Sinatra’s incredible vocal talent and his enduring legacy as one of the greatest singers of all time.
4. The Way You Look Tonight
“The Way You Look Tonight” is a classic romantic ballad that was originally written for the 1936 film “Swing Time.” Frank Sinatra’s version of the song, recorded in 1964, is widely considered to be the definitive interpretation of the tune. With its gentle, lilting melody and sweet, affectionate lyrics, “The Way You Look Tonight” is a perfect love song that captures the magic and wonder of falling in love. Sinatra’s smooth, crooning vocals are perfectly suited to the song’s romantic tone, and the lush, orchestral arrangement only adds to its timeless appeal. The song’s enduring popularity is a testament to Sinatra’s incredible talent and his ability to capture the hearts of listeners with his powerful and emotive voice. “The Way You Look Tonight” is a true classic that continues to be beloved by generations of music fans.
5. I’ve Got You Under My Skin
“I’ve Got You Under My Skin” is a classic love song that was written by Cole Porter in 1936. Frank Sinatra’s version of the song, recorded in 1956, is widely considered to be one of his greatest performances. With its upbeat tempo and memorable melody, “I’ve Got You Under My Skin” is a timeless classic that captures the excitement and passion of falling in love. Sinatra’s smooth, crooning vocals are perfectly suited to the song’s jazzy, swing-inspired arrangement, and his powerful voice effortlessly conveys the intensity of the song’s lyrics. The song’s memorable refrain and catchy melody have made it a beloved favorite among fans of Sinatra and classic pop music alike. “I’ve Got You Under My Skin” is a true classic that continues to be celebrated for its timeless appeal and Sinatra’s incredible vocal talent.
6. I’ve Got The World On A String
“I’ve Got the World on a String” is an upbeat, jazzy tune that was recorded by Frank Sinatra in 1953. Written by Harold Arlen and Ted Koehler, the song is a celebration of life and the feeling of being on top of the world. Sinatra’s powerful vocals perfectly capture the infectious energy of the song, and his effortless delivery and smooth, swinging style make it a true classic. The song’s lively, upbeat tempo and memorable melody have made it a favorite among fans of Sinatra and classic pop music. “I’ve Got the World on a String” is a timeless classic that continues to be celebrated for its infectious energy and Sinatra’s incredible vocal talent. Whether you’re feeling down or just need a pick-me-up, this song is sure to lift your spirits and put a smile on your face.
7. That’s Life
“That’s Life” is a song that was made famous by Frank Sinatra in 1966. Written by Dean Kay and Kelly Gordon, the song is a celebration of perseverance and the ups and downs of life. Sinatra’s powerful vocals perfectly capture the gritty, soulful energy of the song, and his emotive delivery and raw, passionate style make it a true classic. The song’s driving beat and catchy melody have made it a favorite among fans of Sinatra and classic pop music. “That’s Life” is a timeless classic that continues to be celebrated for its powerful message of resilience and Sinatra’s incredible vocal talent. Whether you’re feeling down on your luck or just need a reminder to keep pushing forward, this song is sure to inspire and uplift you.
8. New York, New York
“New York, New York” is a classic anthem that was made famous by Frank Sinatra in 1979. Written by John Kander and Fred Ebb, the song celebrates the city that never sleeps and the endless possibilities of the American dream. Sinatra’s powerful vocals perfectly capture the energetic, soaring spirit of the song, and his emotive delivery and bold, brassy style make it a true classic. The song’s iconic melody and unforgettable chorus have made it a favorite among fans of Sinatra and American popular music. “New York, New York” is a timeless classic that continues to be celebrated for its powerful message of hope and Sinatra’s incredible vocal talent. Whether you’re a native New Yorker or just someone with dreams of making it big, this song is sure to inspire and excite you.
9. My Kind Of Town
“My Kind of Town” is a classic song that was made famous by Frank Sinatra in 1964. Written by Sammy Cahn and Jimmy Van Heusen, the song celebrates the city of Chicago and its unique culture and charm. Sinatra’s powerful vocals perfectly capture the upbeat, optimistic spirit of the song, and his smooth, swinging style makes it a true classic. The song’s catchy melody and memorable lyrics have made it a favorite among fans of Sinatra and American popular music. “My Kind of Town” is a timeless classic that continues to be celebrated for its powerful message of hometown pride and Sinatra’s incredible vocal talent. Whether you’re a proud Chicagoan or just someone who appreciates the unique character of American cities, this song is sure to make you smile and tap your feet.
10. Strangers In The Night
“Strangers in the Night” is a classic love song that was recorded by Frank Sinatra in 1966. Written by Bert Kaempfert, Charles Singleton, and Eddie Snyder, the song is a romantic ballad that captures the feeling of meeting someone new and falling in love. Sinatra’s smooth, crooning vocals are perfectly suited to the song’s romantic tone, and his powerful voice effortlessly conveys the intensity of the song’s lyrics. The song’s memorable melody and catchy chorus have made it a beloved favorite among fans of Sinatra and classic pop music alike. “Strangers in the Night” is a true classic that continues to be celebrated for its timeless appeal and Sinatra’s incredible vocal talent. Whether you’re falling in love for the first time or just need a reminder of the magic of romance, this song is sure to touch your heart.
Darren Jamison 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.
