is one of the most iconic jazz singers the world has ever known. With her unique voice and emotional depth, she has contributed numerous classics to American music culture. Her songs, often steeped in melancholy and life experience, continue to captivate generations. But what are her absolute masterpieces? Here’s a list of Billie Holiday’s top 10 songs.

10. Easy Living

Easy Living is a laid-back track that allows the subtle nuances of Holiday’s voice to shine through. The song celebrates the simplicity and comfort of life—a sentiment that resonates with many. At a time when Holiday’s own life was far from simple, this song offers a glimpse into an idyllic world.

9. As Time Goes By

Famous from the classic film “Casablanca,” As Time Goes By gains another dimension in Billie Holiday’s rendition. The timelessness of the song and the way Holiday injects emotion into the lyrics make this an indispensable performance. The song feels like a nostalgic journey through time.

8. You Go to My Head

This song beautifully illustrates the blending of infatuation and the feeling of being lost in that love. The orchestration swirls around Holiday’s voice, creating an almost intoxicating experience. It’s as if love itself is intoxicating; a masterpiece of emotional depth.

7. On the Sunny Side of the Street

In the pantheon of jazz classics, “On the Sunny Side of the Street” unquestionably deserves a spot. Originally written by Jimmy McHugh and Dorothy Fields, the song received a unique interpretation when Billie Holiday lent her voice to it. What’s remarkable about Holiday’s version is the optimistic, almost carefree atmosphere she creates—quite noteworthy given her often emotionally charged repertoire.

6. Solitude

Solitude is one of those songs where Holiday’s vocal artistry is on full display. The loneliness feels almost palpable, as if Holiday isn’t just singing it, but experiencing it. This song lingers long after you’ve heard it.

5. Blue Moon

Blue Moon is a song that has been covered by many artists, but Billie Holiday gives it her own unique twist. She approaches the song with a subtle sensitivity, making it shimmer like a moon in the dark night.

4. April in Paris

April in Paris feels like a dream, a brief escape to a romantic fantasy. It pays homage to the beauty of spring in Paris, but also to universal feelings of longing and hope.

3. All of Me
In All of Me, Holiday showcases her ability to imbue each word with emotion. The song speaks of total surrender, a sacrifice of the self for love. It’s impossible not to be moved by the raw honesty of this song.

2. Strange Fruit

Strange Fruit is a powerful protest song against racism and lynchings in the American South. The song is not just one of her best works, but also an important social document that exposes America’s raw wounds.

1. I’ll Be Seeing You

Perhaps one of Holiday’s most emotionally charged songs, I’ll Be Seeing You is both a farewell and a promise of reunion. It evokes feelings of loss and hope, showcasing the versatility and depth of Holiday’s artistic expression.