Frank Sinatra Popular Song Rankings [2025]

South Of The BorderFrank Sinatra29rank/position

South Of The Border (Remastered)

There are many different situations that come to mind when we talk about summer.

This piece, “South Of The Border,” is a sparkling work that’s perfect as background music for a daytime drive or an elegant dinner.

Composed in 1939, it features a lively melody that depicts a trip to Mexico, and today it’s cherished as a classic summer jazz standard.

It has been covered by various jazz singers, but this time we’ve picked the especially popular version by Frank Sinatra.

Take Me Out To The Ball GameFrank Sinatra30rank/position

Frank Sinatra and Gene Kelly – Take Me Out to the Ball Game

Many commercials for the Spacia, a light-height wagon targeted at families, depict scenes of going out together as a family, don’t they? In those ads that portray a fun-filled day, they use a cover of “Take Me Out to the Ball Game,” made famous by Frank Sinatra.

Compared to the original, it has a much more pop and cheerful feel, and it even features original lyrics, making it the kind of song that lets you imagine a day when you’ve bought this car and are heading out with your family!

The Christmas WaltzFrank Sinatra31rank/position

Frank Sinatra – The Christmas Waltz (Official Video)

Set to a waltz-like rhythm, this classic sung by Frank Sinatra warms the heart with lyrics that capture the magic of Christmas.

Released in 1954, the song was also included on Sinatra’s Christmas album, “A Jolly Christmas from Frank Sinatra.” Set against a Christmas backdrop, it gracefully depicts wintry scenes such as frosted windows and candlelight.

It’s perfect not only for couples to enjoy together, but also as background music for Christmas parties with family and friends.

The Girl From IpanemaFrank Sinatra32rank/position

The Girl From Ipanema (2008 Remastered)

Here is a representative bossa nova song released by Antônio Carlos Jobim in 1962.

Since it’s a bossa nova piece, there are versions in both Portuguese and English, but the English version famously features vocals by Astrud Gilberto, the wife of João Gilberto.

The Way You Look TonightFrank Sinatra33rank/position

Frank Sinatra – The Way You Look Tonight

Frank Sinatra has released many songs suitable for couples’ anniversaries.

Among them, this 1964 cover is loved by couples of all ages.

The original was performed by Fred Astaire and comes from the film Swing Time.

Theme from New York, New YorkFrank Sinatra34rank/position

Theme From New York, New York (2008 Remastered)

The song you often hear in Kirin Ichiban Shibori commercials was created as the theme for the 1977 film “New York, New York.” It was originally sung by Liza Minnelli, but the version covered by Frank Sinatra later became the most well-known.

It’s said to have been used in the Ichiban Shibori commercials since 2012.

For some reason, that relaxed brass sound perfectly fits the vibe of a beer commercial, doesn’t it?

This TownFrank Sinatra35rank/position

Frank Sinatra – This Town

This is the perfect insert song from the movie Ocean’s 11 for April Fools’ Day.

It’s a track about Las Vegas, the city famous for being a place where your life can be turned around at the casino.

One of the characters said he shook hands with Frank Sinatra.

A must-see.