Top 5 Songs From the Legend Billie Holiday!

Written by: Vincent Nijenhuis


Billie Holiday is a legend. Mostly known being the jazz songstress, and rightfully so, but, unfortunately, like so many queer people of her time, her queerness is often erased from the history textbooks since she couldn’t be out due to the social taboos at the time. It redirected most of her material to not include gender pronouns when discussing her love life or simply conform to the heteronorm and include male pronouns. So, with that in mind, let’s celebrate this queer woman’s music by acknowledging her queerness with a top five of her songs on this very, VERY queer blog. Okay? Okay.

  1. Riffin’ The Scotch (“Riffin’ The Scotch” 1935)

You can hear Billie Holiday’s youth here. It’s not the fact that she was merely eighteen when she recorded this, but the vibrancy and naivety in her voice that seems to sing only for the desire to be heard. It’s almost shocking that this is her first hit considering the a carefree attitude to this track that is very much absent from the work we now associate her with.

2. Strange Fruit (“Strange Fruit” 1939)

Speaking of work we now associate with Billie Holiday, you simply just cannot not mention “Strange Fruit” when discussing her work. It’s an icon. It is so steeped in our culture that I know an uncomfortable about of white republicans who love this song, yet refuse to acknowledge the subject matter: white people lynching black people simply, because they are black. The lyrics describe the bodies of black people as “strange fruit” simply to rot, and stain the tree with their body as they sway in the wind. Unsurprisingly, given the subject matter, Billie Holiday infuses this track with the sad desperation for a day where black people aren’t being killed for simply the crime of being black. Nearly 80 years later, and that day has still not come.

3. Willow Weep For Me (Lady Sings the Blues 1956)

Perhaps Billie Holiday’s most sensual song, which is somewhat disconcerting considering this is song about a breakup, but there is something about the instrumental and Holiday’s voice that just oozes sexuality on this track. This is the song you put on if you want to set the mood right with a Tinder date, but still want to maintain some class and interest with one another.

4. I’m A Fool To Love You (Lady in Satin 1958)

This a song about the closet. This is a song about being in love. This is a song about the regret, and self-loathing in the middle of the venn diagram when both happen to overlap. Yes, Frank Sinatra originally recorded this in 1951 un-intending this song to be about said things, but when Billie Holiday sings lines like “To share a kiss the Devil has known” and “I know it’s wrong, it must be wrong,” it’s impossible to hear this song outside of her personal queer lens. She has found a love that society will never allow her to have due it being seen as morally wrong, so naturally “it must be wrong” to dare express it as something besides a fault of her own.

5.Saddest Tale

So, this is what I believe the kids would call a ‘deep cut.’ Considering this song has never been officially recorded and only exists, because Billie Holiday made a brief appearance in a short film where she sang this song, and that’s pretty much it, it’s amazing that this holds up to her better work. This song does feed into several stereotypes about black people, so bare that in mind when you hear the seemingly ever present pain in Holiday’s voice on this track.