Billie Holiday Songs Ranked

Eleanora Fagan (April 7, 1915 – July 17, 1959), known professionally as Billie Holiday, was an American jazz and swing music singer. Nicknamed “Lady Day” by her friend and music partner Lester Young, Holiday had an innovative influence on jazz music and pop singing. Her vocal style, strongly inspired by jazz instrumentalists, pioneered a new way of manipulating phrasing and tempo. She was known for her vocal delivery and improvisational skills. Holiday won four Grammy Awards, all of them posthumously, for Best Historical Album. She was inducted into the Grammy Hall of Fame and the National Rhythm & Blues Hall of Fame. She was also inducted into the Rock & Roll Hall of Fame, though not in that genre; the website states that “Billie Holiday changed jazz forever”. Several films about her life have been released, most recently The United States vs. Billie Holiday (2021). Here are all of Billie Holiday’s songs ranked.

Click below and listen to one of the most influential artists of all time. Reminisce the timeless music of Billie Holiday.

10. I’m a Fool to Want You (I’m a Fool to Want You, 1958)

“This is Billie Holiday at a time when she was at her most raw moment. Her voice is not perfect. Every bit of pain and edge sears through this particular recording. And it is glorious. Pure Lady Day.

9. Things Are Looking Up (Things Are Looking Up, 1944)

“There is no mistaking the ache in her soul as she tells the tale of her tragic love. As always, it is impossible to separate her life from her music, they are too closely and inextricably entwined.”

8. It’s Like Reaching for the Moon (Giants Of Jazz: Billie Holiday, 1979)

“Melancholic vocal jazz, with a very heartfelt performance by Billie Holiday. Instrumentally its very par for the course, a bit troubling considering how heartfelt these performances are that they are given a generic jazz instrumentation.”

7. You Go to My Head (Solitude: Billie Holiday Story, Vol. 2, 1993)

“In the late 1930’s Billie Holiday rapidly established herself as the leading female vocalist of the jazz world. Almost all of her work is worthwhile hearing. From this very fertile period comes “You Go to My Head”, a standout record from a very strong bunch of late 30’s singles. Its delicate, whistful arrangement supports her vocal craft perfectly.”

See more: Billie Holiday Albums Ranked

6. Solitude (Billie Holiday Sings, 1952)

“Another great release by Billie Holiday. This record got an especially full and warm sound, and displays her voice in a very fresh and vital way. Responsible for the rhythm accompaniment is, among others, The Oscar Peterson Trio.”

5. Deep Song (The Lady Sings, 1956)

“There is a reason why Lady Day is among the handful of artists that is still talked about over 50 years from the day she left this earth. Her raw honesty and emotion will forever resonate with anyone that has rolled the dice of life.”

4. Strange Fruit (The Indispensable Artie Shaw, Volume 5/6 (1944–1945), 1986)

“Strange Fruit is quite simply one of the most remarkable songs you will ever hear. Its dark, poetic imagery is one of a kind. This song (about lynching in the South of the USA) challenged the notion that jazz should simply be about entertainment and good times. When Billie Holiday’s record company, Vocalion, refused to release the song, she switched to Commodore Records. The small Commodore label is now best-known for this song.”

See more: Albert King Songs Ranked

3. Detour Ahead (Detour Ahead, 1960)

“This is some tough stuff with incredibly powerful and dark lyrical themes. I wasn’t aware that music this old dealt with issues like this. I love the dark and grimy feel of this song as well. As good as music from this time frame gets I think.”

2. Them There Eyes (Them There Eyes, 1959)

“Far from being cutesy, Billie holiday’s performance on Them There Eyes is absolutely first-rate vocal jazz. Her idiosyncratic sense of rhythm is in evidence here; she is almost always singing behind the beat. Her ability to do this marks her out as a jazz musician; her voice is the instrument with which she improvises. She has great fun with this material, speeding up and then slowing down at will.”

1. Our Love Is Different (Our Love Is Different, 1939)

“I had this CD in an LP, absolutely loved it and had missed hearing it. “Lady” tears your heart out, but she knows how to deliver a ballad. You can hear the sadness and heartache in her voice. The old standards that have been selected are some of the best and they’re beautifully done in “Lady’s” own inimitable style.”