The Most Popular Frank Sinatra Song, Ranked

Choose the song you think is the most popular!

Author: Gregor Krambs
Updated on Jun 19, 2024 06:54
Fans of Frank Sinatra often engage in lively debates over which of his songs stands out as the finest. Such discussions reveal a diverse range of musical tastes and preferences within his extensive catalog of hits. A ranked list of his songs, determined by fan votes, can serve as a useful tool for both new listeners seeking a gateway into Sinatra's music and longtime admirers looking to see where their favorites place. Engaging with this interactive ranking not only provides insight into the communal preferences of Sinatra’s audience but also influences the list itself. Every vote cast contributes to the dynamic nature of the rankings, ensuring current and accurate reflections of the collective opinion. This process allows each participant to have a direct impact on celebrating Sinatra's legacy.

What Is the Most Popular Frank Sinatra Song?

  1. 1
  2. 2

    Fly Me to the Moon

    Popularized by Sinatra, this song is often played in space missions.
    • Released: 1964
    • Album: It Might as Well Be Swing
  3. 3

    Strangers in the Night

    A song that became Sinatra's first number one hit on the adult contemporary charts.
    • Released: 1966
    • Album: Strangers in the Night
  4. 4

    New York, New York

    An anthem for New York City, often associated with Sinatra's swagger.
    • Released: 1980
    • Album: Trilogy: Past Present Future
  5. 5

    The Way You Look Tonight

    A song that has become a standard for romantic occasions.
    • Released: 1964
    • Album: Days of Wine and Roses, Moon River and Other Academy Award Winners
  6. 6

    I've Got You Under My Skin

    A song that showcases Sinatra's ability to blend with the orchestra, making it a timeless classic.
    • Released: 1956
    • Album: Songs for Swingin' Lovers!
  7. 7

    That's Life

    A song that Sinatra used to reflect on the ups and downs of his own life.
    • Released: 1966
    • Album: That's Life
  8. 8

    Summer Wind

    A song that captures the ephemeral nature of summer love.
    • Released: 1966
    • Album: Strangers in the Night
  9. 9

    Come Fly with Me

    The title track of one of Sinatra's most famous albums, encapsulating the spirit of the jet age.
    • Released: 1958
    • Album: Come Fly with Me
  10. 10

    It Was a Very Good Year

    A reflective song about growing older, showcasing Sinatra's emotional depth.
    • Released: 1965
    • Album: September of My Years

Missing your favorite song?

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About this ranking

This is a community-based ranking of the most popular Frank Sinatra song. We do our best to provide fair voting, but it is not intended to be exhaustive. So if you notice something or song is missing, feel free to help improve the ranking!


  • 203 votes
  • 10 ranked items

Voting Rules

A participant may cast an up or down vote for each song once every 24 hours. The rank of each song is then calculated from the weighted sum of all up and down votes.

Additional Information

More about the Most Popular Frank Sinatra Song

My Way
Rank #1 for the most popular Frank Sinatra song: My Way (Source)
Frank Sinatra, known as "Ol' Blue Eyes," is one of the most iconic singers of the 20th century. His smooth voice and charismatic style left a lasting mark on the music world. Among his vast catalog, one song stands out as the most popular. This song captures the essence of Sinatra's talent and charm.

Sinatra's career began in the 1940s. He quickly rose to fame with his unique voice and style. He sang with big bands before going solo. His ability to convey emotion through song made him a favorite among fans. He recorded many hits, but one song became a defining piece of his legacy.

This song was released in the late 1960s. It came at a time when Sinatra was already a well-established star. The song's lyrics tell a story of self-reflection and resilience. It speaks to the human experience and the journey of life. Many people find the song relatable and inspiring.

The song's melody is simple yet powerful. It complements the lyrics perfectly. Sinatra's delivery is confident and sincere. His voice carries the weight of the song's message. This combination makes the song memorable and timeless.

Over the years, the song has been covered by many artists. Each rendition adds a new layer of interpretation. However, Sinatra's version remains the most beloved. His performance of the song is often seen as the definitive version.

The song's popularity has endured for decades. It has been featured in movies, commercials, and television shows. It is often played at significant events and celebrations. The song's universal appeal transcends generations.

Sinatra performed the song many times during his career. Each performance was met with enthusiasm from the audience. The song became a staple in his concerts. Fans would often request it, knowing it was a highlight of his shows.

The success of this song solidified Sinatra's place in music history. It showcased his vocal abilities and emotional depth. The song's impact is still felt today. It continues to be a source of inspiration and comfort for many.

Sinatra's ability to connect with his audience through this song is a testament to his talent. He had a way of making each listener feel like he was singing directly to them. This personal touch is one of the reasons the song remains so popular.

In conclusion, Frank Sinatra's most popular song is a masterpiece of music and emotion. It captures the essence of his artistry and continues to resonate with listeners. The song's enduring appeal is a testament to Sinatra's legacy as one of the greatest singers of all time.

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