Frank Sinatra Popular Song Rankings [2025]

I’ll Remember AprilFrank Sinatra22rank/position

I’ll Remember April (Remastered)

A classic Western song with a moody vibe by Frank Sinatra—who also flourished as an actor—that’s perfect for listening to in April.

Starting his career as a singer in the 1930s, Sinatra produced many hit songs.

Even today, his supple, sophisticated baritone captivates listeners.

It’s a recommended classic to enjoy while gazing at cherry blossoms with a lover or on your own, letting you savor a touch of grown-up elegance.

It also makes ideal background music for enjoying spring with a drink in hand.

Let me Try AgainFrank Sinatra23rank/position

Let me Try Again [with Japanese translation] Frank Sinatra

The 2018 Google commercial “Google Pixel: Shot with Top Shot” boldly features Frank Sinatra’s classic song ‘Young at Heart.

’ Using this song can make any scene feel epic and dramatic, and as this ad shows, you can even create such a grand atmosphere when paired with missed shots.

It’s a funny commercial that’ll make you chuckle.

Moon RiverFrank Sinatra24rank/position

Moon River Frank Sinatra

This is a wedding song by Frank Sinatra, whose unique oldies vibe and strong support from the jazz and soul scenes have solidified its popularity.

The track has an excellent, refreshing sense of style, making it a great song with the right atmosphere to listen to in September.

My Funny VallentineFrank Sinatra25rank/position

Frank Sinatra – My Funny Valentine

When you hear the famous jazz standard “My Funny Valentine,” do you first think of a vocal version or an instrumental one? In this article, I introduce Frank Sinatra’s vocal rendition, but the tune has been covered in many forms by numerous musicians—for example, Miles Davis featured it as the opening track on his 1957 album Cookin’, and Jim Hall and Bill Evans covered it at a much faster tempo than the original on their classic album Undercurrent.

The song was originally composed by Richard Rodgers—who left an indelible mark on American music with his vast body of work, particularly in musical theater—for the musical Babes in Arms, with lyrics by Lorenz Hart, Rodgers’s well-known collaborator.

By the way, among jazz singer covers, Chet Baker’s vocal version is also extremely famous.

It appears on the West Coast jazz classic Chet Baker Sings, released in 1956.

One For My Baby (and One More for the Road)Frank Sinatra26rank/position

Frank Sinatra – One For My Baby (Live At Royal Festival Hall / 1962)

Originally a melancholic track performed by Fred Astaire in the 1943 musical “The Sky’s the Limit.” It has been recorded by many artists, including Bing Crosby and Iggy Pop.

The most famous version by Frank Sinatra was released in 1954.

September Of My YearsFrank Sinatra27rank/position

The September Of My Years

Frank Sinatra, the most commercially successful jazz vocalist in the world, is held in very high esteem in the United States.

During the time he was active, Christmas songs were unusually popular, and he released many of them.

Since anything he put out would sell, I imagine he made a bundle.

His “September of My Years” is one of his hits, crafted as an orthodox jazz song with an autumn theme.

Someone to Watch Over MeFrank Sinatra28rank/position

“Someone to Watch Over Me” Frank Sinatra

Frank Sinatra was a quintessential American jazz singer active from 1935 to 1995.

“Someone to Watch Over Me” was used as the theme song for Nomura Real Estate’s Proud commercials, featuring an arrangement by Hajime Mizoguchi, a cellist, composer, and music producer.