10 Best Billie Holiday Songs of All Time (2023)

Let’s talk about one of the most iconic jazz singers of all time – Billie Holiday. She was born as Eleanora Fagan in 1915, but you probably know her better as Lady Day. Her childhood wasn’t easy, with a musician father who was often absent and a single mother. But that didn’t stop her from living life to the fullest.

In her 26-year-long career, Lady Day completely transformed jazz music and singing with her unique style. Her improvisational vocal skills were something else – she could make her voice flutter like Lester Young’s tenor or as intense as Louis Armstrong’s trumpet, all in just one syllable! And let’s not forget her iconic hits like “What a Little Moonlight Can Do” and “Strange Fruit” that made her a mainstream success in the 1930s and 1940s.

Sadly, Lady Day’s health started to deteriorate in the late 1940s and 1950s, and she passed away in 1959 at the young age of 44 from cirrhosis. But despite her short life, she accomplished a rare feat for jazz singers of that time – she wrote many of her own songs.

The great Langston Hughes once said that the blues are “laughing to keep from crying.” And boy, did Lady Day convey that paradox with her smoky voice! Her insatiable appetite for life mixed with the terrible things that life had done to her, making every note she sang unforgettable.

So, in honor of this legendary diva, I want to share my ten favorite Billie Holiday songs with you. These songs are steeped in history and just as incredible as she was. So, grab a drink and take a seat – you won’t want to miss these!

10. “God Bless the Child”

This hit song, written by Holiday after a fight with her mother about money, won her a posthumous place in the Grammy Hall of Fame in 1976. “God Bless the Child” is a powerful commentary on the value of independence and self-sufficiency, heavily referencing the Bible in its lyrics.

9. “Them There Eyes”

While Holiday is widely known for her slow ballads, “Them There Eyes” showcases her love for rhythm and swing. With its catchy call-and-response band improvisations, this song is bound to make you want to dance the night away.

8. “All of Me”

If you’re in the mood for a heart-wrenching jazz ballad, look no further than “All of Me.” Holiday’s version of this jazz standard, recorded with her friend and muse Lester Young, is a poignant plea for love dipped in bittersweet memories.

7. “Easy Livin'”

Holiday’s vocals effortlessly blend with the magical playing of Teddy Wilson on piano, Buck Clayton on trumpet, Walter Page on bass, and Young on tenor sax in this 1937 hit. “Easy Livin'” captures the mood of relaxation and taking it easy, with a cigarette in hand.

6. “Lover Man”

Another popular jazz standard that is linked to Holiday is “Lover Man,” which she recorded in 1941, the same year she married James Monroe. Unfortunately, Monroe was an abusive playboy who introduced her to opium. This introduction paved the way for her later struggles with heroin addiction, which was further fueled by another no-good musician she dated, Joe Guy. Holiday’s 1958 live version of “Lover Man” is particularly poignant, reflecting her ongoing search for a “lover man” who would treat her right.

5. “Billie’s Blues (I Love My Man)”

Holiday’s first copyright was “Billie’s Blues (I Love My Man),” which she first recorded in 1936 with Artie Shaw and later in 1944 with Eddie Heywood and His Orchestra. This song was improvised during the recording session and was suggested by Bernie Hanighen, who had recommended that she sing a blues song. “Billie’s Blues” became Holiday’s first solo recording and is also known by the hook “I Love My Man.”

4. “Solitude”

Duke Ellington’s 1934 composition “Solitude” is one of my favorite Billie Holiday songs. It’s a hauntingly beautiful reflection on the loneliness of loss, and Holiday’s melancholy voice perfectly captures the song’s mood. Despite the nostalgia in her words, the breezy accompaniment creates a stark contrast, making the song a timeless classic.

3. “Blue Moon”

If you’re a fan of American music, you’ve probably heard “Blue Moon,” a jazz standard written by Rodgers and Hart in 1934. This record has been featured in several MGM motion pictures and has been performed by famous singers such as Frank Sinatra, Rod Stewart, Ella Fitzgerald, and Bob Dylan. Billie Holiday’s 1952 version of “Blue Moon” is particularly outstanding, despite the toll that drugs and alcohol took on her voice later in life.

2. “Strange Fruit”

Written by Abel Meeropol, “Strange Fruit” is a powerful and influential song that highlights the horrors of lynching. Despite its significance, Holiday faced opposition from the record labels, and it was only released on Commodore Records after her heart-wrenching a cappella performance moved the executive Milt Gabler to tears. The song is a poignant reminder of the ongoing fight against racism.

1. “I’ll Be Seeing You”

“I’ll Be Seeing You” is a sentimental jazz classic that became particularly popular during World War II when families missed their loved ones who were fighting overseas. Written by Sammy Fain and Irvin Kahal, the song was also recorded by Bing Crosby and reached No. 1 on the radio in 1944. Holiday’s version, accompanied by Eddie Heywood and his Orchestra, is one of the most well-known and emotional renditions of the song.


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