Frank Sinatra Popular Song Rankings [2025]

Winter WonderlandFrank Sinatra36rank/position

Google app: Especially in the cold winter

Frank Sinatra is one of the most famous jazz vocalists in the world.

“Winter Wonderland,” which was used as the song for Google’s ‘The Colder the Winter’ commercial, is one of his signature tracks.

His warm voice is so soothing.

You make me feel so youngFrank Sinatra37rank/position

Frank Sinatra- You make me feel so young

A popular song composed by Josef Myrow and Mack Gordon in 1946.

It has been recorded by many artists, including Chet Baker and Ella Fitzgerald.

The version by Frank Sinatra, featuring his youthful and captivating vocals, was released in 1956.

Younger Than SpringtimeFrank Sinatra38rank/position

Younger Than Springtime

Frank Sinatra is known as a world-renowned jazz vocalist.

While he achieved legendary fame, he was also dogged by dark rumors, such as the FBI revealing his very close ties with the Italian-American Mafia.

For better or worse, he was an artist who was always in the spotlight.

The spring-themed song “Younger Than Springtime,” associated with him, is a work by Art Farmer, a leading figure in standard jazz, and it gained worldwide popularity.

The Girl from IpanemaFrank Sinatra39rank/position

Frank Sinatra – The Girl From Ipanema ft. Antonio Carlos Jobim | A Man And His Music (1967)

Sinatra has all kinds of images associated with him, but like a true professional showman, he gave a light, effortless rendition of The Girl from Ipanema.

Before I knew it, I was drawn into the stage and tapping my foot to the rhythm.

It felt as if the stage itself was ingrained in him, like a born entertainer.

New York, New YorkFrank Sinatra40rank/position

New York, New York – On the Town

This is a song from On the Town.

It tells the story of a few days in which Navy sailors enjoy their shore leave in New York City.

The feeling of freedom when they hit the town comes through in the brisk pace of the music and the energetic, dashing choreography.

It’s a piece grounded in the lively, upbeat spirit typical of classic musicals.

Night And DayFrank Sinatra41rank/position

Frank Sinatra – Night And Day (1957 version)

Here is a song Cole Porter wrote for the 1932 musical The Gay Divorcee, first performed by the tap-dance master Fred Astaire.

It was later released as a record and became so popular that it reached number one in the United States.

His songs often have long verse sections, and their distinctive qualities, including unique chord progressions, have made them beloved jazz standards for both vocalists and instrumentalists.

The lyrics are passionate, expressing how the singer thinks of their beloved night and day.