Revisiting Lady Day: Nass Recommends the Billie Holiday Catalogue


“And I am sweating a lot by now and thinking of / leaning on the john door in the 5 SPOT / while she whispered a song along the keyboard / to Mal Waldron and everyone and I stopped breathing”

— Frank O’Hara “The Day Lady Died” 


What is it about Lady Day that just keeps me coming back for more? There’s something about her music that I can’t quite find in anyone else. For the Nass’s annual womxn’s issue, I’d like to take a look at the artistry of the great Billie Holiday, the woman I consider to be the finest jazz vocalist of the twentieth century. 

My first exposure to Holiday was, in fact, not from hearing her in the video game Fallout 3. Indeed, I distinctly remember my particular pride at recognizing her wavy contralto on Galaxy News Radio, the in-game swing radio station of post-apocalyptic Washington, D.C. Man, my eighth-grade-self thought, I sure am cultured, aren’t I? as I fired my plasma gun at hordes of mutated ants.

The more I think about it, though, I can’t remember how I would have first heard her. I came across most of my favorite blues and jazz artists when I was twelve and thirteen by reading old interviews. Paul McCartney said he wrote “Michelle” while listening to Nina Simone, and some of Duane Allman’s last recordings were with Aretha Franklin. Perhaps, then, I first came across Holiday in an interview with Frank Sinatra. In 1958, he told Ebony magazine:


With few exceptions, every major pop singer in the US during her generation has been touched in some way by her genius. It is Billie Holiday who was, and still remains, the greatest single musical influence on me. Lady Day is unquestionably the most important influence on American popular singing in the last twenty years.


But no, that quotation couldn’t have been my first exposure to Lady Day. I remember coming across Sinatra’s words around that same age, but when I clicked around the internet for them, I found an entry on her own Wikipedia page under the section “Vocal Style and Range.” I had intentionally sought out information on a performer I was already familiar with. Maybe I had already found her name dropped elsewhere. 

Maybe my old music teacher, Lisa Briggs, was the first to introduce me to the great jazz singer. Ms. Lisa, as all of her students affectionately called her, was certainly the person who, aside from my dad, had most turned me onto older music––perhaps even more than she was teaching me to play piano in the last year or so before I stopped taking lessons. We once spent an entire session on a Tuesday night playing a Beatles trivia game, after which my parents, paying-fifty-bucks-an-hour, were decidedly not as happy as I surely was. Billie Holiday could very easily have been one of the many names she threw at me each week in her continuing effort to educate me in the breadth and depth of twentieth-century musical history. 

That said, her enthusiasm kick-started mine to a level sustained ever since––an enthusiasm that compelled me to comb YouTube and iTunes and my parents’ and relatives’ CD collections for any good music they might have. Sure, at first, I only listened to late sixties rock and roll, but pretty quickly I made progress as both a listener and independent thinker. I expanded my tastes to anything that sounded powerful. Billie Holiday’s music, in whatever form I might have first encountered it, clearly fit the bill.

The attempt to examine my personal musical history and ascertain the roots of my love for my favorite artist seems to have come up with largely nothing. I expound on it not just to win points for my cultural literacy, but also to illustrate the way her influence persists in a manner both obvious and invisible. Though her cultural and musical relevance is undeniable, she, nonetheless, takes a back seat to several other more prominent jazz artists who are some of the strongest and most cemented names in vocal jazz, black and white alike. Louis Armstrong, Frank Sinatra, Ella Fitzgerald, Nat King Cole, and Dean Martin, all wonderful vocalists in their own distinct ways, are all significantly closer to household names than Billie Holiday, particularly among listeners who would not necessarily describe themselves as jazz fans. 

Am I claiming that Billie Holiday is underrated? Not necessarily, though I have gone on the record in this publication with the claim that “Stairway to Heaven” is underrated, by which I still stand strong. I will contend, though, that Billie Holiday is perhaps undeservedly pigeon-holed in a way that does a disservice to her artistic power. 

Perhaps she occupies a kind of sideline niche because the other top-regarded vocalists of the genre occupy such decisively powerful ones. Louis Armstrong, for instance, remains front and center of jazz tradition, carrying the torch of the genre well past his grave as the founder and popularizer of jazz, buoyed by his distinctive gravelly voice and his timeless renditions of “When the Saints Go Marching In” and “What a Wonderful World.”

 Ella Fitzgerald acts as a kind of counterpoint to Armstrong, her silky pure alto contrasting his rougher tones in their legendary collaboration albums of the late 1950s. Couple that with her incredible ability to scat-sing––the ability to improvise vocally with doo-dah-like syllables and a key tool in a jazz singer’s arsenal––she’s an unstoppable force of vocal jazz. 

As for people like Sinatra, Martin, and Cole? They’re crooners who primarily peddle in beautiful love songs beautifully sung, popular to our parents and grandparents. I say this not as put down––I adore all of their music––but their general accessibility at least partially explains such staying power. 

Unlike the other artists I’ve named, Billie Holiday is just not as immediately accessible. She doesn’t grab you or soothe you in the same way that many of these other vocalists can, an asset in a culture that progressively places jazz within either the staid esoterism of classical or the dreaded realm of easy listening. Holiday’s comparative inaccessibility seems to stem from two sources: her repertoire and her specific vocal style. 

Much of Billie Holiday’s music is rather slow and mournful. She doesn’t have the same pep or sprightliness as Louis or Ella, but her slowness isn’t the kind you can dance to at a wedding or at prom like you might to Sinatra’s rendition of “The Way You Look Tonight.” Instead, she sings plaintively and wistfully of lost loves with a melancholy so fierce that it’s a wonder her influence on Frank Sinatra extended into his artistry instead of just bumming him out all the time. 

Consider Holiday’s other most famous song, “Strange Fruit,” where she sings about the horror of black lynching in the American South. Samuel Grafton wrote about it in The New York Post in 1939, “If the anger of the exploited ever mounts high enough in the South, it now has its ‘Marseillaise’.” The lyrics are sufficiently graphic to merit such a description, as Holiday sings, “Scent of magnolias, sweet and fresh/Then the sudden smell of burning flesh.” Indeed, “Strange Fruit” is about as far from “Fly Me to The Moon” as you can get. 

Her catalogue does indeed contain a number of upbeat hits. “Them There Eyes” could be considered an archetype of the jumping jazz number. Her rendition of Cole Porter’s “Let’s Do It (Let’s Fall in Love)” is the definitive cover of the popular standard. Nonetheless, her catalogue just doesn’t pop like many of those contemporaries I’ve named. No, Billie Holiday is decidedly not as attractive in this sense. But at least her voice is pleasant, right? 

All told, Billie Holiday’s vocal style is actually rather thin and somewhat raspy. And when it is raspy, it’s not like Armstrong, whose rasp is all-encompassing and charming. Instead, Holiday’s rasp more often betrays a vocal deficit, alarming her more careful listeners. This deficiency is most evident in her later recordings. I am of course not arguing that Billie is a bad vocalist; her talent is indisputable. But she perhaps doesn’t occupy the same category as someone like Ella Fitzgerald or Etta James, whose vocal power and control are so extraordinary that it can be overwhelming. No, Billie Holiday’s talent manifests subtly.

That subtlety doesn’t just reside in her vocal technique, though. It’s an emotional subtlety that permeates the very essence of any of her recordings. Sure, it’s reflected in the way she manipulates her voice, but it’s technique that she manipulates to suggest emotion. Instead, she dives into the wells of her emotion to inform her technique or lack thereof. Ray Ellis, orchestrator and conductor for her penultimate album Lady in Satin, agreed:


I would say that the most emotional moment was her listening to the playback of “I’m a Fool to Want You.” There were tears in her eyes… After we finished the album I went into the control room and listened to all the takes. I must admit I was unhappy with her performance, but I was just listening musically instead of emotionally. It wasn’t until I heard the final mix a few weeks later that I realized how great her performance really was. 

The aspects of her artistry that make her slightly less accessible than other household name jazz vocalists are exactly the reason so many other jazz fans, me included, love her so much. Billie Holiday reflects the softer, more intentional side of jazz often lost in even the best of Ella Fitzgerald or Nat Cole. Holiday’s catalogue exhibits levels of sophistication, depth, and maturity that transcend any analyses of vocal tone or technique. In honor of Womxn’s History month, let’s celebrate the great Billie Holiday. There’s a reason Frank O’Hara was so moved by her death that he felt compelled to write his iconic poetic tribute. Beyond the crooning Sinatra or the crackly Armstrong or the suave Martin, let’s remember Billie Holiday, the singer who understood that jazz, that music, is about conveying the totality of one’s emotion in ways that otherwise cannot be done.