41 years after her death, Billie Holiday was inducted into the Rock and Roll Hall of Fame. She “changed jazz forever,” claims their website. They’re right! Billie’s haunting voice has lingered in music collections for years. Audiences are still spellbound by a woman who came from such pain and poverty, yet created such beauty.
Holiday was born in 1915 to a single, teen mother. She received almost no formal education, and was soon running errands in brothels and scrubbing floors. Holiday then started singing and performing in nightclubs around Harlem, and was finally “discovered” by John Hammond. Hammond organised her debut singles, “Your Mother’s Son-In-Law” and “Riffing the Scotch”, which were released when Billie was just 18. Ultimately, Holiday–nicknamed “Lady Day” by Lester Young–released very few albums, as that era was more about singles distributed on 78 RPM records. So here are, in my humble opinion, 10 of her best songs.
The Best of Billie Holiday: 10 Must-Listen Tracks
“Strange Fruit”
Although Holiday grew up without her father, Clarence Halliday, she reconnected with him during her teen years. She decided to cover the haunting anti-lynching anthem to honour him after he was denied medical assistance due to his ethnicity. “Strange Fruit” was written by Abel Meeropol and has been described as “the first unmuted cry against racism” by Leonard Feather. The poem, and Holiday’s performance, has been credited with being “the beginning of the Civil Rights movement” by Ahmet Ertegun, and its cultural and musical significance cannot be overstated.
Southern trees bear a strange fruit
Blood on the leaves and blood at the root
Black bodies swingin' in the Southern breeze
Strange fruit hangin' from the poplar trees
Pastoral scene of the gallant South
The bulgin' eyes and the twisted mouth
Scent of magnolias sweet and fresh
Then the sudden smell of burnin' flesh
Here is a fruit for the crows to pluck
For the rain to gather, For the wind to suck
For the sun to rot, For the tree to drop
Here is a strange and bitter crop
“God Bless the Child”
Billie worked with and supported her mother at various points through her life. This, understandably, led to tension between the two, and resulted in many fights. During a particularly difficult row, Billie’s mother supposedly shouted “God bless the child that’s got his own”, which inspired the song. “God Bless the Child” features a soft choral arrangement, surely very different to the passion of the argument. The lyrics discuss what people owe to one another. Knowing Billie’s rags-to-riches story and her lifelong financial instability, it’s hard not to be moved by the idea of her writing this tragic song.
“Carelessly”
“Carelessly” was recorded with Teddy Wilson and his orchestra, and the song has a lengthy introduction where the other musicians work their magic. While the whole song is just over three minutes, Billie only sings eight lines. Yet within this frame, Billie tells a story of regret, love and loss. The orchestra sandwiches the lyrics between a jazzy, somewhat upbeat tune which almost ironically juxtaposes the heartbreak.
How carelessly you gave me your heart
And carelessly I broke it, sweetheart
I took each tender kiss you gave to me
Every kiss made you a slave to me
Then carelessly I told you good-bye
But now at night I wake up and cry
I wish I knew a way to find the love
I threw away so carelessly
“I’ve Got My Love to Keep Me Warm”
Like a number of other songs on this list, “I’ve Got My Love to Keep Me Warm” has been covered lots of times. Some notable versions are sung by Fred Astaire, Doris Day, Frank Sinatra and Ella Fitzgerald. Billie was first, though! Because “I’ve Got My Love to Keep Me Warm” is about cold weather, it’s been included in plenty of Christmas and holiday albums. It’s a fun, swinging, upbeat song about love and resilience, and Billie’s voice is beautiful and distinctive.
“Solitude”
If “I’ve Got My Love to Keep Me Warm” is one of Billie’s happiest songs, “Solitude” is one of the saddest. The accompaniment is breezy and soft, but the lyrics cut deep: “In my solitude/ you haunt me/ with reveries/ of days gone by”. Music critic Ted Gioia said that Billie sang with “with the world-weariness of the words matching to an almost disturbing degree her late-career persona”. Billie’s life started hard and didn’t get easier, but it’s nice to know that she wasn’t alone in her sadness: she had music.
“Lover Man”
“Lover Man” is one of Billie’s best-known songs, possibly because it was inducted into the Grammy Hall of Fame in 1989. The version on her album, also called “Lover Man”, is great, but many fans’ favourite version is the live song recorded in 1958. At the time, Billie was married to Louis McKay, an abusive mob “enforcer” who stole all her money. A year later, she died.
“My Sweet Hunk of Trash”
Speaking of terrible husbands…. This hilarious duet, which Billie recorded with the incomparable Louis Armstrong, works as a conversation between a couple where each bemoans the other’s failures. There’s still some affection, and it’s not dissimilar to Ella Fitzgerald’s “My Funny Valentine”. Billie’s soft, high melodies contrast with the rasp of Armstrong, and Sy Oliver’s orchestra is the perfect companion.
“Them There Eyes”
Let’s continue with another upbeat, fun song. “Them There Eyes” was originally written by Maceo Pinkard, Doris Tauber and William Tracey, and has been covered by Peggy Lee, Bing Crosby and Ella Fitzgerald. You can hear the amusement in Billie’s voice as she sings about being “so happy”, and then pauses for the orchestra to really let rip. It’s a jazz classic, easy to dance to, and simply wonderful.
“What a Little Moonlight Can Do”
So much of music is a collaboration between the singer and the band, and I would argue that this is more present in jazz because of the space for improvisation. Billie recorded “What a Little Moonlight Can Do” with Teddy Wilson and his orchestra, who seem to relish in the gaps between the lyrics where they can really stretch their fingers across the pianos or let the trumpets shine. Billie’s voice seems full of happiness in the partnership, and the result is magic
“I’ll Be Seeing You”
Let’s finish with a song which isn’t, perhaps, the most well-known of Billie’s songs now, but meant the most to people when it was released. Recorded in 1944, when many families were separated due to the Second World War, “I’ll Be Seeing You” is a simple lament to those who aren’t there. It’s heartbreaking, and gorgeous, and perhaps comforting to know that you’re not alone in your grief.
One Essential Billie Holiday’s Album?
During the 1930s and 1940s, the music industry was primarily focused on releasing singles. At that time, most recordings were distributed on 78 RPM records, which typically held one song per side. It wasn’t until the late 1940s and 1950s, with the introduction of the 33 1/3 RPM LP (long-playing) records, that albums as we know them became more common.
Therefore, Billie Holiday frequently recorded songs in studios to be released as singles, or as part of collections on compilations later on. Some of her most famous recordings from that time were compiled into albums long after their initial release.
Yet, if we were to recommend one Billie Holiday albums, it would be:
Lady Sings the Blues
1956, Clef records
Lady Sings The Blues gathers fresh tracks with reimagined versions of her classics, including “God Bless the Child” and “Strange Fruit.” With stripped-down arrangements and a voice marked by years of hardship, Holiday brings her struggles and victories to the forefront. As one of her later releases, it offers a raw, introspective glimpse into her life. Yes, essential!
From the 1956 session
Billie Holiday: vocals; Paul Quinichette: tenor saxophone; Charlie Shavers: trumpet; Tony Scott: clarinet; Wynton Kelly: piano; Kenny Burrell: guitar; Lenny McBrowne: drums; Aaron Bell: bass
From the 1954 session
Billie Holiday: vocals; Willie Smith: alto saxophone; Harry Edison: trumpet; Bobby Tucker: piano; Barney Kessel: guitar; Chico Hamilton: drums; Red Callender: bass
Billie Holiday’s Death
Billie Holiday’s life came to a tragic end on July 17, 1959—a pivotal year in jazz history. She was only 44. Her body, ravaged by years of heavy drinking, could no longer hold on, and she died of cirrhosis of the liver in a New York City hospital. There was no peaceful rest for her even in her final moments—police officers stood guard at her door, having arrested her for drug possession while she lay dying. Despite her immense talent, Holiday’s life was a relentless fight against addiction and the harsh realities of a world that too often sought to crush her. Her voice, full of pain and beauty, lingers on, but the woman behind it was broken long before her body gave out.