Billie Holiday’s Popular Song Rankings [2025]

Summer TimeBillie Holiday15rank/position

Billie Holiday – Summertime

George Gershwin, who worked across a wide range of genres—from opera and musicals to film scores, orchestral works, and concertos—was active in both popular and classical music and is even called a composer who helped create American music.

Among the many masterpieces he produced, let’s look at the timeless standard “Summertime,” a song that continues to be covered across all musical genres, not only jazz but also soul and pop.

Composed as an aria for the groundbreaking 1935 opera Porgy and Bess—remarkable at the time for its all-Black cast—the piece is sung by the heroine as a lullaby within the story.

Although it has inspired an enormous number of cover versions, the first to achieve widespread popular success is said to be the rendition sung in 1936 by the legendary female jazz singer Billie Holiday.

Among covers by white artists, the version performed by the equally legendary rock singer Janis Joplin is especially famous.

Despite being a song in which the lyrics play a crucial role, countless jazz musicians have also performed it as an instrumental, which shows how its universal, superb melody continues to captivate the hearts of musicians and listeners alike.

ve Got My Love to Keep Me WarmBillie Holiday16rank/position

Billie Holiday – I’ve Got My Love to Keep Me Warm

A heartwarming swing jazz tune that wouldn’t feel out of place in an old coffee shop, “I’ve Got My Love to Keep Me Warm.” It’s a song about how, even though it’s cold outside, my heart is warm—and of course, the reason is a lover’s presence.

With lyrics that shine in their simplicity and care—using a single “love” to mean both a lover and the feeling of love, and “snowing” to express that it’s snowing—the song avoids adding unnecessary notes.

Billie Holiday, who lived through an extremely hard and intense life socially and culturally, brings a voice imbued with melancholy and wistfulness—never quite exuberant—which truly resonates with the heart.

I’ll Be Seeing YouBillie Holiday17rank/position

Billie Holiday – I’ll Be Seeing You (Audio)

In the years just after the war, the exquisite love song sung by America’s Billie Holiday was etched deeply into people’s hearts.

While longing for a lover from whom she’s been separated, she layers the beloved’s image over everyday scenes—the morning sun, the moonlight, a merry-go-round—expressing those feelings with her uniquely rich, sultry voice.

Recorded in 1944, the piece resonated with many and was even used in 2019 as the final communication from the Mars rover Opportunity.

Its gentle, nostalgic melody and heartfelt sentiments make it a song that comforts anyone who wishes to be reunited with someone dear.

Lady Sings The BluesBillie Holiday18rank/position

Billie Holiday – Lady Sings The Blues (Audio)

Billie Holiday’s timeless classic “Lady Sings the Blues.” Chosen later as the title of a biographical film, this song has never lost its luster despite the many years since its 1956 release.

Blending the depth of jazz with the pathos of the blues, it feels as if the piece transforms her life of struggle and defiance into music.

The richly expressive performance with orchestra underpins Holiday’s stirring vocals.

With an unfailing instinct for spinning out jazz melodies, her voice quietly moves those who listen.

It is truly a masterpiece that embodies exactly why Western music from the ’50s continues to be loved today.

Stormy WeatherBillie Holiday19rank/position

Stormy Weather

Billie Holiday, the female jazz vocalist who won popularity with her richly expressive voice, is one of the key figures who changed the very concept of jazz singing.

This piece is a torch song about a heartbreaking breakup: ever since her lover left, the weather—both inside her heart and out in the world—has been stormy.

Her searing emotional expression, as if reflecting her own tumultuous life, deeply moves those who listen.

First performed in 1933, the song became a widely loved standard—so much so that a musical film of the same name was made in 1943—and Holiday’s recording can be heard on the classic album “An Evening with Billie Holiday.” It’s perfect for a long autumn night, lost in thought.