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Home Best Songs Guide

10 Best Frank Sinatra Songs of All Time

List of the Top 10 Best Frank Sinatra Songs of All Time

Edward Tomlin by Edward Tomlin
March 31, 2023
in Best Songs Guide
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10 Best Frank Sinatra Songs of All Time

Frank Sinatra Songs of All Time

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Frank Sinatra, also known as Ol’ Blue Eyes or The Voice, was an American singer, actor, and producer. He was one of the most popular and influential musical artists of the 20th century. Sinatra’s distinctive voice, phrasing, and interpretation of songs made him a legend in the music industry. He was known for his ability to connect with his audience and his charm both on and off stage.

Sinatra began his music career in the 1930s as a member of the Big Band era. He went on to have a successful solo career, recording hit songs such as “My Way,” “Fly Me to the Moon,” and “New York, New York.” He also starred in numerous films throughout his career, including “From Here to Eternity,” which won him an Academy Award for Best Supporting Actor.

Sinatra’s impact on popular culture was immense, influencing artists from multiple generations and genres. He is widely regarded as one of the greatest vocalists of all time, and his contributions to the music industry have earned him a place in the Grammy Hall of Fame, the Songwriters Hall of Fame, and the Rock and Roll Hall of Fame.

Sinatra passed away in 1998 at the age of 82, leaving behind a legacy that continues to inspire and influence generations of musicians and music lovers.

Table of Contents

  • 1. “That’s Life”
  • 2. “Strangers In The Night”
  • 3. “New York, New York”
  • 4. “Fly Me To The Moon”
  • 5. “My Way”
  • 6. “Summer Wind”
  • 7. “I’ve Got You Under My Skin”
  • 8. “The Way You Look Tonight”
  • 9. “I’ve Got The World On A String”
  • 10. “My Kind Of Town”

1. “That’s Life”

“That’s Life” is a timeless classic song recorded by the iconic American singer Frank Sinatra in 1966. The song features Sinatra’s unmistakable voice and a swinging, brass-heavy arrangement that perfectly captures the energy and optimism of the era. The lyrics tell the story of a man who refuses to give up in the face of life’s ups and downs, using a mix of witty wordplay and heartfelt emotion to convey the message of resilience and determination. “That’s Life” is a beloved anthem of the American spirit, and remains one of Sinatra’s most enduring and beloved hits to this day.

2. “Strangers In The Night”

“Strangers in the Night” is a classic song by Frank Sinatra, released in 1966. The track is characterized by its unforgettable melody, sweeping orchestration, and Sinatra’s iconic vocal performance. The lyrics describe a chance encounter between two strangers who are drawn to each other, despite the uncertainty and fleeting nature of their connection. “Strangers in the Night” has become one of Sinatra’s signature songs, earning him a Grammy Award for Best Male Pop Vocal Performance in 1967. Overall, the song is a testament to Sinatra’s enduring legacy as one of the greatest performers in the history of popular music.

3. “New York, New York”

“New York, New York” is a classic song that has become synonymous with Frank Sinatra. The song was first introduced in the Martin Scorsese film of the same name, and has since become an iconic anthem of the city that never sleeps. The song is a celebration of New York City, with lyrics that describe the city’s energy, glamour, and allure. The upbeat tempo and soaring melody make it a favorite at weddings and celebrations, while its connection to the city has made it an enduring part of popular culture. Sinatra’s powerful and emotional performance on the song has become a defining moment in his career, and cemented his status as one of the greatest vocalists of all time.

4. “Fly Me To The Moon”

“Fly Me to the Moon” is a classic song made famous by the legendary crooner Frank Sinatra in 1964. The song features Sinatra’s smooth, velvet voice and a lush orchestral arrangement that perfectly captures the romantic and adventurous spirit of the lyrics. Written by Bart Howard, the song’s memorable melody and lyrics about a journey to the moon have made it an enduring classic of the American songbook. “Fly Me to the Moon” remains a beloved and iconic song, and a testament to Sinatra’s talent as a singer and interpreter of classic songs.

5. “My Way”

“My Way” is a beloved song by Frank Sinatra, released in 1969. The track is characterized by its powerful lyrics, which describe a person reflecting on their life and the choices they’ve made. Sinatra’s commanding vocal performance adds to the song’s emotional impact, conveying both regret and a deep sense of pride in one’s individuality. “My Way” has become a timeless classic, covered by numerous artists over the years, and a testament to Sinatra’s enduring influence on popular music. Overall, the song is a powerful tribute to the human spirit and the unique paths we each carve out in life.

6. “Summer Wind”

“Summer Wind” is a classic Frank Sinatra song that captures the essence of summertime romance. Released in 1966, the song features a jazzy arrangement with a swing rhythm and soaring strings that perfectly complement Sinatra’s smooth vocals. The lyrics describe a fleeting summer romance that is bittersweet in its brevity, capturing the feeling of longing and nostalgia for a love that has come and gone. The song has become a timeless classic and has been covered by numerous artists over the years, cementing its place as one of Sinatra’s most beloved hits.

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, with music and lyrics by Cole Porter. The song features Sinatra’s powerful vocals and a brassy, big-band arrangement that perfectly captures the intensity and passion of the lyrics. The song tells the story of a man consumed by the love of a woman who has gotten under his skin, and has become one of Sinatra’s most iconic hits. “I’ve Got You Under My Skin” is a testament to the enduring appeal of Sinatra’s music and the timeless songwriting of Cole Porter, and remains a beloved classic of the American songbook.

8. “The Way You Look Tonight”

“The Way You Look Tonight” is a classic song by Frank Sinatra, released in 1964. The track is characterized by its gentle, romantic melody, sweeping orchestration, and Sinatra’s smooth, crooning vocals. The lyrics describe a person’s love and admiration for their partner, celebrating their beauty and unique qualities. Sinatra’s delivery captures the song’s tender sentiment, conveying both vulnerability and a deep sense of passion. “The Way You Look Tonight” has become a timeless classic, covered by numerous artists over the years, and a testament to Sinatra’s enduring influence on popular music and the art of romantic balladry.

9. “I’ve Got The World On A String”

“I’ve Got the World on a String” is a classic Frank Sinatra song that was released in 1953. The song was written by Harold Arlen and Ted Koehler and has since become one of Sinatra’s most popular tracks. The upbeat and catchy tune speaks of the feeling of being on top of the world and having everything under control. Sinatra’s smooth vocals and the accompanying big band sound perfectly capture the joyous and carefree sentiment of the song. “I’ve Got the World on a String” has since been covered by many artists and remains a timeless classic that continues to be enjoyed by generations.

10. “My Kind Of Town”

“My Kind of Town” is a classic song by Frank Sinatra, which celebrates his hometown of Chicago. The upbeat and swinging tune is filled with references to the Windy City and the famous landmarks that make it special. Sinatra’s smooth and powerful voice brings the lyrics to life, evoking feelings of nostalgia and pride in the listener. The song’s catchy melody and optimistic lyrics make it a perennial favorite for fans of Sinatra and of classic American music. It is a true testament to Sinatra’s enduring legacy as one of the greatest entertainers of all time.

Edward Tomlin

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.

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