Billie Holiday is one of the foremost vocalists in jazz, whose emotional depth and unique phrasing inspired generations of singers to experiment with form and pitch fluctuation. Nicknamed “Lady Day” by the saxophonist Lester Young, her star brightened in the 1930s behind a string of hit songs and notable live performances in Harlem. In what was the hottest jazz scene in the country, Holiday stood out, and in 1937 she joined the famed Count Basie Orchestra; a year later, the clarinetist Artie Shaw asked her to join his orchestra, making Holiday the first Black woman to work with a white big band.
Holiday’s legend grew in the late ’30s during her residency at the Café Society in Manhattan. She was introduced to “Strange Fruit,” a song by Abel Meeropol about lynching in the American South based on a poem he had written. Barney Josephson, the proprietor of Café Society, heard the song and brought it to Holiday, who first performed it there in 1939. It was a watershed moment for the singer: It’s not only the most famous song in her repertoire, it’s considered one of the most important in history, the track’s vivid imagery a strong indictment of racism in the country. Holiday was officially a star after the recording of “Strange Fruit,” and followed it with an impressive run of tracks in the early ’40s that cemented her fame.
While there’s been a notion to only associate Holiday with pain and struggle, these accounts have dimmed her light as a firebrand artist whose creative bravery encouraged others to take similar risks. We asked 10 musicians and writers to share their favorite Holiday songs: Enjoy listening to their choices, check out the playlists and be sure to leave your own selections in the comments.
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‘Autumn in New York’
José James, vocalist
Within the first two seconds of this song it’s impossible not to be drawn into the spell of Billie Holiday’s voice. Sailing confidently over lush chords by the pianist Oscar Peterson, Holiday pulls back the curtain on the beating heart of everyone who has loved, lost, loved again and (finally) lost themselves in that great city. A superb storyteller, Holiday explores every nuance of Vernon Duke’s paean to autumnal introspection in the city that never sleeps. Through her knowing delivery, every detail becomes vivid, cinematic: couples holding hands in Central Park, clouds reflecting off endless steel buildings, sundown in Greenwich Village, the wry smile of the maître d’hôtel at the Ritz, a lipstick-stained empty cocktail glass left behind at the bar. Billie was queen of it all, one of the highest-paid Black entertainers of her time, who left no stone unturned on her journey toward the self. This is beyond jazz singing; this is mastery in its highest form. With this song, Billie takes her place among the greatest of all balladeer improvisers in the jazz canon, creating the definitive version of an American classic.
▶ Listen on Spotify, Apple Music or YouTube
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‘Porgy’
Nailah Hunter, musician
“Porgy” — particularly her 1948 recording on Decca Records — is one of the best demonstrations of all that Billie Holiday is capable of. It highlights her vocal range (often criticized as “limited”) along with her renowned ability to convey complex emotions. The song is a heartfelt plea from one lover to another, asking for protection from an abusive ex, and you can feel how deeply the lyrics resonate with her — they fit her like a glove. Here, her voice effortlessly floats between deep dread and a tenderness reserved for the most intimate lovers. As ever, the vulnerability in her delivery adds a raw, personal layer to the performance. Holiday’s ability to project seemingly opposing emotions simultaneously is remarkable, moving between languor and a regal stillness with effortless grace. This performance encapsulates the essence of her artistry, revealing the depths of her emotional landscape and solidifying her legacy as a true vocal powerhouse.
▶ Listen on Spotify, Apple Music or YouTube
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‘Sophisticated Lady’
Nia Andrews, vocalist
Talk about a woman who lived. I remember first hearing her voice as a girl on vinyl at the library, and how it sparked curiosity about the pain I detected in her voice though I couldn’t yet name it. Somewhere along my journey as a woman I found my way back to this song, this time knowing love, loss and the ravages of life more intimately. I nod slowly in recognition as I listen to the stories in Billie’s tone, alone. The lyrics are the cherry. I could nerd out about how special her phrasing is, too, but this one for me is all about her longing, like she’s singing into a mirror. Duke Ellington composed this before lyrics were written, and it’s been recorded so, so many times. His version is bright and charming and impressive (like he was). Billie’s version is no less masterful in its depth in my opinion. Hers gets me right in the guts. Sonically, it’s a teary-eyed smile thinly veiling an ache at the back of the heart. It’s a quiet, wistful ride after a fancy night out to find yourself alone. But for all its melancholy, there’s a wink in there. Maybe even a shrug.
▶ Listen on Spotify, Apple Music or YouTube
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‘Good Morning Heartache’
Melissa McMillan, singer-songwriter
This song is a perfect example of Billie Holiday’s mastery of nonchalant, effective and ultimately human storytelling. Before she sings a single note the instrumentation sets up a somber tone, from the low winds to the aching strings to the taunting piano lines. Her tone and delivery immediately embody all that the intro has alluded to. She works in tandem with everything; she never oversings or overshadows the elements around her, but shares the space with the orchestration creating the melancholy atmosphere.
She delivers the lyrics without flashy performance. It’s a straightforward conversation, which is exactly how you might imagine someone deeply heartbroken would speak to you. The bridge presents a bit more urgency, and with the slightest of vocal variations from Billie, a plea is delivered — a little more volume and a slightly more nasal placement to fill out the sound is all it takes. Her impact is certainly still felt today; vocalists who employ a deeply personal, soul-baring approach can trace this style directly back to Billie Holiday and the blues singers of the early 20th century.
▶ Listen on Spotify, Apple Music or YouTube
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‘God Bless the Child’
Elena Bergeron, Times editor
It’s a coldblooded line. Deriving from an argument with her mother over money, one or the other of the women (it’s unclear which) said “God bless the child that’s got his own” when it became clear that the parent could not — or would not — provide. The line might have referred to a Bible verse, but the offer of Scripture instead of material assistance had to have felt like bitter bread.
It became the silvery narrative thread for the song co-written by Holiday and the composer Arthur Herzog Jr. in 1939 that’s since become a standard of the American songbook. Holiday’s versions, with sly lyric tweaks and varied pacing, show her brilliance as an interpreter, in this case of the hard-knock gospel of self-sufficiency. There’s her arch nod to the stinginess of some forms of charity — “Rich relations give, crust of bread and such / you can help yourself, but don’t take too much” — that always makes me wonder if she’s touting the virtue of meekness or offering a grifter’s advice: Don’t draw attention to a con you might run again.
In the chorus, that mama and papa “may have” is treated as inconsequential: That’s not our business. But there’s a sweetness, a knowing salute, to the self-sufficient child in the way Holiday stresses and stretches the word — CHI-iiild, ch-EYE-ld — that centers our concern. The repetition that ends the phrase (“that’s got his own, that’s got his own”) lands like a pat on the head to underscore the lesson. Holiday could stroll the ballad or turn it bluesy, lagging a step behind the beat or dialing up her vibrato like a trumpeter. But I always thought of it as a melancholic lullaby (as in this 1950 rendition with the Count Basie Orchestra): She gathers us chirren for a message. The earlier you learn it, the better.
▶ Listen on Spotify, Apple Music or YouTube
Find the full playlist on Spotify and Apple Music:
‘Strange Fruit (Live)’
Allison Russell, singer-songwriter, poet and activist
Billie Holiday died July 17, 1959. This version of “Strange Fruit” was recorded just prior. She first recorded the song in 1939. The words come from a poem by Abel Meeropol, a Jewish American who was moved to write it after seeing images of a lynching in a newspaper. All the pain of the world and Billie’s beleaguered life under rampant racism can be heard in this 1959 rendition. “Strange Fruit” was and is a protest song nonpareil, unfortunately still relevant and resonant today. Billie’s world-wounded voice compels us from beyond the grave. As America fractures and frays, I turn to the artists and ancestors who remained truth tellers despite oppression, abuse and violence. Billie was hounded by government agencies who tried to silence her — specifically they did not want her singing “Strange Fruit.” For 20 years she resisted and closed every set with it. You cannot listen to this recording and remain unmoved. A lament and a freedom song for the ages from one of the greatest artists and freedom singers America has ever produced.
▶ Listen on YouTube
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‘Fine and Mellow’
Willard Jenkins, jazz writer
This staging of Billie Holiday singing her own tune “Fine and Mellow” is a performance I like to think of as Billie’s blues essence mode. It’s taken from an immortal document in the annals of televised jazz, the 1957 CBS production “The Sound of Jazz.” In this performance, Lady Day, who appears easeful and in splendid spirits, is surrounded by a cast of fellow hall of famers, including Roy Eldridge and Doc Cheatham on trumpets, Coleman Hawkins, Ben Webster and Lester Young on tenor saxophones, Gerry Mulligan on baritone sax, Vic Dickenson on trombone, Milt Hinton on bass, Osie Johnson on drums, and Billie’s then-current pianist Mal Waldron.
Billie is in good voice, exhibiting a true sweetness in her expressions, the cameras capturing her priceless facial nuances as she luxuriates in several solos during the performance. It’s all here: the expertly crafted mellow blues, Billie’s loving, quite telling facial expressions (particularly telling as her dear friend Lester, whom she nicknamed “Pres,” solos and a cameraman captures her love throughout his break), and her supremely relaxed vocal and aesthetic command of the blues. She positively inhabits “Fine and Mellow.” This is Billie truly as “one of the cats,” thoroughly immersed in the music, demonstrating perhaps her purest jazz performance on tape.
▶ Listen on YouTube
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‘Solitude’
Kilo Kish, musician, artist and designer
Billie Holiday sings masterfully about sadness and longing for what’s gone in “Solitude.” The songwriting is special in its vagueness, allowing the question of “who” or “what” to arise within us. The sparseness of the music and her pauses let the ideas linger in such a beautiful way. The haunting melody and her tone evoke a deep questioning — what of longing, loneliness and grief? Her voice is like a deep well, not just filled with pain but also genuine curiosity. There’s a self-awareness that makes her delivery so special. For some reason when I listen to this, I don’t worry so much, for her or for me. I sense the possibility of new beginnings in her voice. Her words are steeped in despair, yet she still feels solid, confident and somewhat protected from the pain she sings about, carrying a secret strength that resonates with me. I love this doubleness that occurs when Billie sings. Vulnerability and strength become one and the same.
▶ Listen on Spotify, Apple Music or YouTube
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‘Detour Ahead’
David Renard, Times senior editor
“Detour Ahead” was the first Billie Holiday song that really hit me between the eyes. I’m not completely sure why; I had heard other, better-known tracks of hers before this one. I think it’s something about the opening words of the lyric — “Smooth road, clear day” — and the way her voice slides up the syllables and back down the other side. To use the song’s road-trip metaphor, it’s like cresting a little hill and being able to see the whole horizon spread out. “Detour Ahead” is the inverse of a tune like “Lush Life,” where Johnny Hartman radiates warmth even though he’s telling a bleak story; Holiday here sounds like she sees black clouds following her on sunny days. But the narrator has hope that maybe this time it won’t all end in a wreck — the lyric changes to “no detour ahead” — and you want that for her.
▶ Listen on Spotify, Apple Music or YouTube
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‘I’ll Be Seeing You’
Victoria Canal, singer-songwriter
I have a soft spot for songs that fool you in their delivery, attaching themselves to whatever association you most need. I tend toward the melancholy and relish nostalgia — Billie Holiday’s “I’ll Be Seeing You” lies in the crux of that emotional breadth. You could be slow dancing with your first love for the last time, or riding a bike with your dad in the sun on a Saturday, or grieving a best friend in your later life, or sitting by the window on a spring day with incense going and a good novel in your lap. The same song can lie perfectly underneath a variety of beautifully nostalgic scenes of our lives. This song has accompanied me, personally, through a long list of bittersweet goodbyes. Packing up my first flat, hugging my first deep adult relationship goodbye, sharing a eulogy at my grandfather’s funeral … for me, this song gently holds grief, cloaked in sweetness. Billie’s delivery is so relaxed, so tender, and the gentle arrangement could only be described as joyful — but to me, it’s a confession of being haunted by the thing you wish most to have, that can no longer be yours.
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https://www.nytimes.com/2025/04/02/arts/music/billie-holiday-jazz-music.html
