11 Iconic Billie Holiday Songs You Need To Hear

Jazz history has no shortage of heartbreak, addiction and triumph in the face of adversity, but the story of iconic jazz singer Billie Holiday is up there with the most captivating. In this article, we chart the rise and fall ofLady Day’ – as she was often called – through some of her most famous performances.

From original compositions, improvising genius and collaborations with some of the most famous jazz musicians in history, stay tuned for our pick of the best Billie Holiday songs. Together they highlight a true jazz revolutionary and an artist who would influence everyone from Nina Simone and Frank Sinatra to Erykah Badu and Amy Winehouse.

Billie Holiday singing at a New York jazz club in February 1947
Billie Holiday, New York, Feb. 1947, credit William P Gottlieb (public domain)

Born Eleanora Fagan in 1915 Philadelphia, a turbulent childhood featured a disappearing jazz musician father, an appearance in juvenile court aged just 9 and odd-jobs running errands for a local brothel.

Two things would set the youngster onto a totally different path though…

Firstly, discovering the music of Louis Armstrong and Bessie Smith introduced her to the world of jazz.

Then, in her early teens, she relocated to Harlem, New York, to be with her mother, placing her at the heart of one of the most vibrant places in jazz history.

Immersing herself into the early 1930s scene (and changing her name to pay tribute to the actress Billie Dove and her jazz musician father Clarence Holiday) she performed extensively at Harlem nightclubs, often with tenor saxophonist Kenneth Hollon.

Producer John Hammond was an early admirer, who arranged her debut recording session, in 1933, as a guest of Benny Goodman.

We pick up the story of best Billie Holiday songs here, ahead of her first featured recording in 1935.

Billie Holiday songs

What a Little Moonlight Can Do 

Single with Teddy Wilson & His Orchestra (rec. 1935)

John Hammond’s support of Billie Holiday (who he described as “an improvising jazz genius”) led to him signing her to the Brunswick record label.

Often hailed as her first big break, What a Little Moonlight Can Do was recorded for the burgeoning jukebox business, as a co-production with pianist Teddy Wilson.

The single charted well and led the record label to invest in Billie Holiday as an artist of her own accord.

Played at a swift tempo, Holiday improvises a variation on the melody in a way which would become widely imitated but never equalled.

Teddy Wilson’s group features solos by Benny Goodman and Ben Webster, the out-chorus joyfully led by Roy Eldridge.

Easy Living 

Single with Teddy Wilson and Lester Young (rec. 1937)

Written for a film of the same name, Easy Living is from another session with Teddy Wilson, this time starring Count Basie Orchestra rhythm section Freddie Green, Walter Page and Jo Jones.

Like What a Little Moonlight Can Do, this number was widely distributed and was part of a collectively evolving shared repertoire amongst musicians known as ‘jazz standards’.

It was her musical partner here, saxophonist Lester Young, who gave her the name Lady Day which stuck for the rest of her career.

Strange Fruit 

Single (rec. 1939)

By the late ’30s Lady Day was an exceptional singer with admirers all over America, but it was the song ‘Strange Fruit’ which made her a household name and an icon of her era.

It was one of her most popular recordings and would stay in her repertoire for the remainder of her career.

The tune is set to a poem about the lynching of African Americans in the Southern United States and has come to be seen as a precursor to the Civil Rights Movement.

Later recorded by Nina Simone too, it was compared by a contemporary journalist to the French national anthem, a song which captures anti-monarchical sentiments in the late eighteenth century.

Fine and Mellow 

Single (rec. 1939)

The B-side of a single is normally reserved for a recording expected to be of less interest than the A-side, but this did not turn out to be the case with the release of Strange Fruit.

On the record’s flipside was Fine and Mellow, which turned out to be a hit unto itself and has been covered by other artists many times since.

It features Billie Holiday singing in a blues style reminiscent of Bessie Smith and Ma Rainey.

God Bless The Child 

Single (rec. 1941)

Another classic recording by Holiday, this piece was penned by the singer herself and she would perform and re-record it throughout her career. As the title suggests, the mood is spiritual and the lyrical content partly autobiographical.

Yet another hit, God Bless The Child further solidified Billie Holiday as a leading artist of the time and has since been awarded a Grammy. Holiday’s voice has reached maturity here, and she has cemented her signature reimagining of melodies and evocative phrasing.

Her self-confidence in pushing through the repertoire she wanted in the face of label resistance is highlighted by her comment that “people don’t understand the kind of fight it takes to record what you want to record the way you want to record it.”

Trav’lin Light 

Single with Paul Whiteman & His Orchestra (rec. 1942)

Paul Whiteman was a bandleader and arranger who ran one of the most famous ensembles in the ’20s. Possibly best known for commissioning George Gershwin’s Rhapsody in Blue, he employed some of the best and most innovative jazz musicians of the day.

Although Whiteman’s popularity was beginning to wane in the ’40s, this showcase for Billie Holiday rose to number one in the charts and was re-released as a V-disc a couple of years later for distribution among American troops.

Lover Man (Oh Where Can You Be?) 

Single (rec. 1944)

An addition to the growing list of Holiday hits was this number specifically written for the singer. Her recording sparked a slew of renditions by numerous vocalists and instrumentalists, and it became a staple of her live performances.

Scored for jazz band and symphonic orchestra, the arrangement is lush and leisurely. Holiday’s tone is full of grief and yearning, as if she’s wailing in her sorrow. The popularity of the recording led to solo concert opportunities normally offered to only the most prominent of pop singers.

I’ll Be Seeing You

Single (rec. 1944)

Written in 1938, this nostalgic jazz song seemed to hit the height of its popularity in 1944 when it was released by Billie Holiday, Bing Crosby and Frank Sinatra.

Billie Holiday’s beautiful treatment of this jazz ballad was released by Commodore Records, who she had just returned to that year, and seems to have entrenched itself as the most famous version of the song.

Towards the end of the decade, she was arrested for narcotics possession and began to fall out of favour with the critics.

Crazy He Calls Me 

Single (rec. 1949)

By the late ’40s, Billie Holiday was at the height of her fame and was accruing sizeable earnings. Despite brushes with the law owing to her ongoing battle with drug abuse, she was selling out huge concert venues.

This period also marks the beginning of a long period of declining health, although no foreshadowing of this is evident in this recording.

Holiday’s voice is full of nimble glissandi and delicate vibrato, using the lyrics to influence the way she reworks the tune.

Lady Sings The Blues 

Album: Lady Sings The Blues (rec. 1956)

Released concurrently with her memoirs of the same name, this song co-written with pianist Herbie Nichols demonstrates two sides of the blues: pensive sadness, and proud swagger.

After a dramatic trumpet flourish, Billie Holiday sings her self-referential lyrics with improvised support from members of the band. She inhabits the two stylistic personalities perfectly, proving her prowess as a consummate storyteller.

I’m a Fool to Want You 

Album: Lady in Satin (rec. 1958)

Whilst she moved from one destructive relationship to another and her health faded throughout the ’50s until her death in 1959, she was still very much in the public eye until the end.

No commentary on Billie Holiday is complete, though, without some mention of Lady in Satin, one of her last albums.

In spite of the condition of her voice, it is considered by many to be one of her most important contributions to the genre.

Cushioned by orchestrations by Ray Ellis in the manner of Nelson Riddle’s famous collaborations with Frank Sinatra, the sessions drew on the Great American Songbook. In a lesser singer’s shoes, Holiday’s fragility could sound feeble, but she manages to sound earthy and sensuous.

Billie Holiday Songs: Further Discovery

Billie Holiday’s short and tragic career gave subsequent generations of vocalists big shoes to fill.

She pioneered new techniques and her collaborations with jazz titans Teddy Wilson, Lester Young, Count Basie and Artie Shaw are milestones in the jazz canon.

Of course, these are just a handful of songs; there are many more which you can still discover as part of Billie Holiday’s legacy.

Besides packing venues and making remarkable albums, she wrote an autobiography which is highly a recommended jazz book.

Her life was also the subject of a 2021 movie entitled The United States vs Billie Holiday which we reviewed.

Lastly, as with the truly great jazz musicians, her legacy lives on; as recently as 2019 she made history again as her recording of I’ll Be Seeing You was used as the final NASA transmission to the Opportunity Rover at the end of its Mars mission!

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