The Incredible Lady Day: 11 Best Billie Holiday Songs

To say the life of Billie Holiday was tough would be a vast understatement. Though she’s now often recognized as one of America’s most influential early contemporary artists, she had to fight one battle after another over the course of her life, never letting the obstacles stifle her voice. Born Eleanora Fagan in 1915, her formative years were spent in extreme poverty. She quit school young so she could get a job and make money for her family.

Due to her admirable persistence, she landed a singing gig in a bar when she was still a teenager. Once she got her foot in the door of the music industry, she became one of jazz’s indispensable figures – nicknamed “Lady Day” – and helped to shape the genre into what it is today. She sold out Carnegie Hall the first time she played there and ended up coming back for over twenty appearances.

Dive into this jazz legend’s setlist with our ranked list of the best Billie Holiday songs.

11. Autumn In New York

“…shimmering clouds in canyons of steel.” As you listen to Billie Holiday’s gently-delivered ‘Autumn In New York,’ a peaceful, wintery picture of The Big Apple takes shape in your mind. Her wistful vocals fall easily on the ear and leave you feeling almost instantly relaxed. A jazz era number that still finds itself as an occasional pick on bar room jukeboxes, the lightly bouncing rhythm and Holiday’s effortless vocal delivery perfectly capture a blustery Manhattan evening, with car headlights peeking through a light dusting of snow flurry as bundled up New Yorkers make their way to cozy lounges and restaurants. The tune captures the essence of Holiday’s catalog, which features the artist in what often seems to be an airy, dream-like state.

10. What a Little Moonlight Can Do

Holiday tunes often take on a languid rhythm, allowing the listener to feel at ease and hit “play” repeatedly as the day goes by. ‘What a Little Moonlight Can Do’ is different because it commands your attention, showing you the broad scope of Holiday’s vocal range and the range of her backing band. Introducing a ragtime rhythm right off the bat, instrumental solos soon take the forefront with sax and trumpet work. Piano dances in the background in tandem with a welcomed shuffling drum beat that summons the listener’s interest. But perhaps the most riveting thing about the fun single, recorded towards the early part of Billie’s career, is the unique way she executes her vocal lines. She was known for being the first to develop a new jazz voicing, using her golden pipes as an instrument like a player rather than a singer. About a minute into the track, this pioneering style is front and center, but only lasts a short while and leaves listeners wanting more.

9. Crazy He Calls Me

A strings section takes this song to new heights, but don’t mistake ‘Crazy He Calls Me’ as just another romantic lullaby. Lyrics like “I say I’ll go through fire… As he wants it, so it will be,” represent a strong image of the song’s main character, a lover declaring her devotion to her soulmate. By the time Billie Holiday began her recording career, powered equipment was making its first strides. She was a part of one of the first generations of artists to make use of the modern-day microphone, instead of having to belt out vocals to theatre crowds without any amplification. This innovation allowed her to sing intimately, critics at first mistaking her for a simple lounge crooner. But the more music she released, the more the industry caught on to her genius ability to marry finesse with power. This duality stands out in ‘Crazy He Calls Me.’

8. Strange Fruit

Nicknamed Lady Day by her devoted bandmates, Holiday’s discography is expansive. During her reign throughout the ’30s and ’40s, she was one of America’s most in-demand live performers. While on stage, she didn’t take traditional performance routes with beckoning gestures for crowds. Instead, many observed she withdrew into herself while singing, almost appearing to be in two places at once. Contrary to what you’d think, audiences loved the authenticity. With her release of ‘Strange Fruit,’ originally penned by Abel Meeropol, came much controversy. Drifting from her tried-and-true subject matter, the single was a standalone protest statement, poetically shining light on the horrors of lynchings taking place in the U.S. Though not her most popular due to the size and durability of her work, it’s one of her signature songs and is a historic symbol for the struggle for freedom. The iconic release comes in at number 8 on our list.

7. You Go To My Head

“I find you spinning ’round in my brain, like the bubbles in a glass of champagne.” Frank Sinatra often cited Billie Holiday as one of jazz’s greatest voices, and he covered several of the songs she recorded as well. ‘You Go To My Head’ is one of those popular jazz numbers, with many of the genre’s most influential acts like Louis Armstrong releasing their own renditions. Originally recorded in her early 20s in 1938, Lady Day’s single release is a definite crowd favorite among her fans. It’s easy to see why. It’s an exemplary recording for both Holiday’s talents and the jazz genre itself. Her vocals are full of vibrato as they soar while she sings to her lover. At 2 minutes in, a passionate clarinet solo by Buster Bailey temporarily takes over. It’s quite possibly one of the most romantic songs ever released; perfect for a Valentine’s Day playlist.

6. April In Paris

“April in Paris. This is a feeling no one can ever reprise.” A classic jazz standard that works in tandem with Holiday’s rendition of ‘Autumn In New York,’ her single ‘April in Paris’ paints a beautiful picture of the world’s most romantic city. Originally written by composer Vernon Duke for the broadway play Walk a Little Faster, fellow songwriters viewed the tune as a big “theatre hit.” Once Holiday got a hold of it though, she recreated the piece, wielding her powerful minimalist approach with plenty of vocal vibrato to spare. This Lady Day tune feels distinctly European, with tender piano rhythm setting a foundation for charming sax and trumpet work. The band’s instrumental delivery is particularly eloquent, and makes the listener feel like they are really experiencing the birth of spring in the City of Love as they listen to the recording.

5. As Time Goes By

“It’s still the same old story. A fight for love and glory.” Holiday comments on the intricacies of romance with ‘As Time Goes By,’ an unhurried recording that involves an inconspicuously profound take on relationships. Lyrics like, “Moonlight and lovesongs, never out of date,” and “Hearts filled with passion, jealousy and hate,” delicately drive home the push and pull that often happens over the course of a developing love affair. Holiday had her own complicated, and often damaging, experiences concerning love, and the melancholy undercurrent generally present in her voice becomes more apparent when singing about this subject matter in particular. Despite her complicated past with the opposite sex she keeps things hopeful and reveals to the listener, “…I will always welcome lovers, as time goes by.”

4. I’ll Be Seeing You

A moving song about mourning those who are no longer in our lives, ‘I’ll Be Seeing You’ is a beloved hit from America’s jazz era. In the early to mid. 1900s, theatres were booming with constant influxes of new plays. This song was originally written for the musical Right This Way by Sammy Fain and Irving Kahal. Though the play didn’t last long on the broadway circuit, many artists like Bing Crosby and Frank Sinatra loved the stirring track and recorded covers of it. Holiday’s version was so powerful, NASA transmitted the 1944 recording to their Mars rover, Opportunity, in 2019 during its final mission (if that doesn’t tug at your heartstrings, I don’t know what will).

3. All of Me

Recognized by the Songwriting Hall of Fame as an important American work and receiving their “Towering Song Award,” ‘All of Me’ is a lasting jazz standard that has long stood the test of time. First composed in 1931 by Gerald Marks and Seymour Simons, it soon made the rounds among popular artists and several different recordings were released. Though greats like Armstrong and Sinatra produced solid renditions, music critics agreed Holiday’s take was the best one, and through her talents she made ‘All of Me’ all her own. Another song that finds Billie expertly singing about the tragedies of love, the story features the main character asking her lover who’s left her, “You took the part that once was my heart.So why not take all of me?” Despite grief-stricken lyrics, piano skips in the background and the music sways, giving the track a joyous mood. This polarity is classic Lady Day, and comes in high on our list at number 3.

2. Blue Moon

This popular track has more of a bluesy feel than other Holiday recordings thanks to piano work that features a bit of attitude. Due to the commercial popularity of ‘Blue Moon,’ it has been a hit many times over for several different artists. Billie’s recording is surprisingly jovial, even down to her vocal delivery, which often contained noticeable, welcomed hints of sadness. It’s hard not to have your mood lifted while you listen to the swaying number, which features a protagonist finally finding love, her “blue moon” turning to “gold.” When you reach for your afternoon coffee for a hit of caffeine, pair it with this chart-topper for a double shot of an afternoon pick-me-up. Though the tune isn’t as striking as other beloved numbers among diehard Holiday fans, its mass appeal and long legacy have made it required listening for any swing-era playlist. And on our own list, it is designated as runner-up.

1. Solitude

Lady Day released the poignant track ‘I’ll Be Seeing You’ in 1944 and moved listeners with her sorrowful performance. But just a few years prior, she released ‘Solitude,’ another deeply sorrowful recording that proved she was the woman for the job when it came to heartbreak jazz classics. Maybe it was her tough upbringing in Baltimore, or her diving in headfirst to the Harlem music scene when she was still in her teens, that allowed her to not just sing the lyrics of these sad songs but actually live out the words on stage for all to see. Her pensive performances evaded theatrics, and that’s why she had such a dramatic effect on listeners. I personally think her lack of professional voice training had a huge impact on her ability to break hearts mid-show with tunes like ‘Solitude,’ no safety of music school quelling the heartache inside her that made her such an unrivaled artist. This bonafide fan-favorite features the singer in all her glory, both haunting and hopeful, and takes the number 1 spot on our list of the best Billie Holiday songs.

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About Ged Richardson

Ged Richardson is the Founder and Editor-in-Chief of He has been featured in Entrepreneur, PremierGuitar, Hallmark, Wanderlust, CreativeLive, and other major publications. As an avid music fan, he spends his time researching and writing about new and old music, as well as testing and reviewing music-related products. He's played guitar in various bands, from rock to gypsy jazz. Be sure to check out his YouTube channel, where he geeks out about his favorite bands.

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