Frank Sinatra Popular Song Rankings [2025]

Have Yourself A Merry Little ChristmasFrank Sinatra8rank/position

Have Yourself A Merry Little Christmas (Remastered)

Have Yourself a Merry Little Christmas is a classic originally written as an original song for the 1944 musical film Meet Me in St.

Louis.

It’s widely known as a quintessential Christmas jazz number.

The lyrics sweetly depict spending Christmas with a lover.

Even today, it remains a beloved standard covered by a variety of jazz vocalists and pop artists, but this time I’ve chosen Frank Sinatra’s rendition, which is among the most famous of the many covers.

I’m A Fool To Want YouFrank Sinatra9rank/position

I’m A Fool To Want You (Remastered 1999)

Frank Sinatra’s 1951 release “I’m a Fool to Want You” is one of the most emotionally expressive songs of his career.

His plaintive vocal delivery deeply moves listeners, conveying the pain and conflict of love with striking realism.

Said to be influenced by his complicated relationship with his former wife Ava Gardner, the song voices a poignant longing for unrequited love.

Featured on Sinatra’s smash album “Where Are You?,” it continues to reign as a masterpiece of the jazz ballad genre.

It’s the kind of track you want to listen to alone on a quiet night, with tears in your eyes.

It Might As Well Be SpringFrank Sinatra10rank/position

It Might As Well Be Spring

This song is striking for its beautiful, heart-stirring melody.

Showcasing Frank Sinatra’s rich expressive power, it vividly captures the longing for spring’s arrival, letting you savor springlike emotions even outside the season.

Written for the 1945 musical film State Fair, it’s included on albums such as Sinatra and Strings (1962).

Listen when you’re tired, and it’s sure to soothe your soul.

Why not play it on a long spring evening and feel the approach of a new season?

Let It Snow! Let It Snow! Let It Snow!Frank Sinatra11rank/position

Frank Sinatra – Let It Snow! Let It Snow! Let It Snow! (Official Music Video)

The world-renowned jazz singer Frank Sinatra.

Even those who aren’t familiar with jazz have probably heard his voice at least once.

When it comes to Frank Sinatra’s Christmas songs, isn’t “Let It Snow! Let It Snow! Let It Snow!” the one that comes to mind? Though it’s a jazz piece, this song—still a modern Christmas classic—features a melody so easy to sing that there’s hardly any difference compared to popular music.

Mistletoe And HollyFrank Sinatra12rank/position

Frank Sinatra – Mistletoe And Holly (Official Video)

The great American singer Frank Sinatra released a Christmas song in September 1957, and since its inclusion on the album “A Jolly Christmas from Frank Sinatra,” it has continued to be loved as a Christmas classic.

Sinatra’s warm vocals gently depict quintessential holiday scenes—mistletoe, holly, Santa Claus, and cozy time with family.

It was even used in a Christmas parade at Tokyo Disneyland.

Why not give it a listen as background music for Christmas with your family and loved ones?

September SongFrank Sinatra13rank/position

September Song

Frank Sinatra, one of the defining entertainers of the 20th century.

His voice, known as “The Voice,” continues to captivate many listeners today.

The autumn classic he sang overlays the season of life with September, depicting the preciousness of spending limited time with a loved one.

Sinatra’s seasoned vocal delivery lends profound conviction to the protagonist’s tender yet bittersweet emotions.

Released as a single by Sinatra in November 1946, the song reached No.

8 on the U.

S.

charts, and was later included on his Grammy-winning album “September of My Years.” It’s also well known from the film “September Affair.” A gem of a ballad, perfect for savoring on a long autumn evening.

That’s LifeFrank Sinatra14rank/position

That’s Life (2008 Remastered)

The film Joker, with its heart-wrenching twists and relentless pacing, features the song “That’s Life,” originally released by Frank Sinatra in 1966.

Its bittersweet yet beautiful lyrics and moving melody—embracing life without denial and laughing in the face of whatever happens—resonate deeply with listeners.

In the movie as well, the song memorably underscores the Joker’s poignancy and sorrow, highlighting how he keeps smiling even while facing all kinds of adversity.