Billie Holiday’s Popular Song Rankings [2025]

I’m a fool to want youBillie Holiday8rank/position

Billie Holiday – I’m a Fool to Want You (Official Audio)

A heart-pounding visual piece portraying the romance between a man and a woman who pass each other on a night train.

The commercial features Audrey Tautou, one of France’s most iconic actresses, famous for the film Amélie.

The song playing is a version of a Frank Sinatra classic covered by Billie Holiday, one of the “Big Three” female jazz vocalists.

It is highly regarded as a masterpiece of torch songs—ballads about lost love and unrequited feelings—and the commercial’s imagery, together with the allure of fragrance, is beautifully expressed through Holiday’s deeply evocative voice.

The human tendency to seek love, even when it isn’t with one’s true match…perhaps that never changes, no matter the era.

Some Other SpringBillie Holiday9rank/position

Some Other Spring

Billie Holiday has produced many classic songs about love and parting, and among them, one that especially symbolizes spring is “Some Other Spring.” Recorded in 1939, this piece showcases Billie’s delicate yet profound expressiveness.

Like spring flowers coming to life, the concept of entrusting the longing and hope for a lost love to a new spring captures the hearts of many listeners.

At the same time, it harbors an icy coldness deep within, where Billie’s true artistry shines.

As spring arrives and one tries to find love again, the past romance remains unforgettable—many listeners surely feel that poignant ache resonating through Billie’s voice.

This work is a masterpiece that brilliantly captures the complex emotions of longing for the fresh beginnings spring brings while still being haunted by a lost love.

When you’re smilingBillie Holiday10rank/position

Billie Holiday – When you’re smiling

It was used as the song in SoftBank’s iPhone 4 commercial.

Since it was recorded in 1929 by Louis Armstrong—affectionately known as “Satchmo,” a jazz trumpeter and vocalist—it has become a jazz standard.

Body and SoulBillie Holiday11rank/position

Body and Soul

Composed by Johnny Green in 1930, this song was written for actress and singer Gertrude Lawrence, but it was ultimately introduced in a Broadway revue by Libby Holman.

To this day, it is a ballad that has been performed, loved, and well known among many singers and instrumentalists.

Among vocal versions, Billie Holiday’s rendition is particularly famous, and the song can be said to suit her character.

Gloomy SundayBillie Holiday12rank/position

Gloomy Sunday – Billie Holiday

Many people may know this song as one of the urban legends.

“Gloomy Sunday” was composed by Hungarian songwriter Rezső Seress, based on the grief of losing his lover.

The song’s influence was considered so strong that it was banned from broadcast in Hungary.

It became known worldwide when jazz singer Billie Holiday covered it in English.

In Japan, Maki Asakawa wrote Japanese lyrics for it, and it was covered by several well-known singers.

On the Sunny Side of the StreetBillie Holiday13rank/position

On the Sunny Side of the Street

A beloved classic that has long been cherished as a standard number, “On the Sunny Side of the Street.” Originally written for a musical, it later became a standard and has been covered by many famous jazz artists such as Louis Armstrong and Benny Goodman.

In Japanese, the title means “On the Bright Main Street,” and true to its name, the piece has a cheerful and relaxed feel.

Speak LowBillie Holiday14rank/position

Billie Holiday & Her Orchestra – Speak Low (Verve Records 1956)

In Kurt Weill’s 1943 stage play One Touch of Venus, the song was performed by Mary Martin.

The play tells the story of a Venus statue coming to life and falling in love, with the song conveying the poignancy of never knowing when she might turn back into stone.

It was adapted into a film in 1948, in which Ava Gardner performed the song.