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I was looking back upon some of my old papers from my earlier college years, as I am wont to do, when I stumbled across a paper that I wrote for my History of Jazz class about the famous jazz singer Billie Holliday. Now, let me tell you, Billie Holliday was QUITE a lady. She’s not only insanely talented, but she is a fire-cracker of a woman.

Now, I chose to write about her because I bought an old vinyl of her greatest hits over break a few years ago because I recognized her name and also because it was on sale (I have never been known to pass up a sale, no matter what it is). I gave it a listen and fell in love with her voice.

Unfortunately, I completely forgot about the paper until the morning it was due, when, upon looking at the syllabus before class, I realized with horror that I was screwed. And then I did something that I am ashamed of to this day… I emailed my professor and said I was sick. I then spent all morning working on it and emailed it to him the second I was done, saying “Oops, so sorry, I forgot to email this in earlier”. I have never been more ashamed in myself. I’m so sorry, professor (whose name I cannot mention because rules).

Moving on from past regrets that haunt me.

I’ve chosen to give Billie Holliday the respect she is due and actually do a decent job writing about here. This is my plan. I’ve got lots and lots to say, so get ready.

Here we go.

We start at the very beginning, which is, I hear, a very good place to start.

It’s April 7th, 1915 in Baltimore (or Philadelphia, depending on what sources you look at. What can I say besides – Billie Holliday: An Enchanting Enigma). Sadie Fagan, a young 13 year old girl has just given birth to a beautiful bundle of joy: Eleanora (spoilers: It’s Billie). The child’s father, however, 15 year old Clarence Holiday, is nowhere to be seen. Clarence was a young aspiring musician with stars in his eyes, looking to make it big with Fletcher Henderson’s band (if you’re not into jazz music or jazz history, Fletcher Henderson is a big deal. According to Wikipedia, he is “one of the most prolific black musical arrangers” and a really, really great bandleader. Usually I try to avoid Wikipedia as a source, but this time they are correct. This time).

Anyway. Sadie tried really hard to be a good mom to her little girl, but, due to the fact that she was a young single parent with hardly no money to her name, this proved to be difficult. Eventually, Sadie decided that the kindest thing she could do for her daughter would be to send her to live with some family members who could take care of her better. Unfortunately, this backfired. The family Eleanora went to live with abused her and did not provide a stable home environment for her, so at the ripe old age of 14, Eleanora went off to join her mother in New York City.

But life on the streets in New York wasn’t all lights and jazz hands. Both Sadie and Eleanora bounced around, getting in trouble with the law fairly often. At one point, both of them spent a bit of time in prison together for prostitution. Despite all of the turmoil and chaos going on in her life, Billie never regretted her move to New York. Because this is where she came into contact with the music that would shape the rest of her life: Jazz.

This new style spoke to her and the young Holiday dove headfirst into music as a means of coping with her surroundings. At this point, I will interject that she had EXCELLENT taste in music. She was super in to Louis Armstrong and Bessie Smith, both of whom were really excellent performers and musicians.

Billie Holiday was one of those terribly annoying children who were just born with astounding talents and didn’t take any voice lessons or anything as a kid. She literally just popped out with this beautiful voice and said “Hello, world, let me sing for you” and the world said “YES”. As a teen, she was able to earn some cash singing at various clubs around town. This is actually when she came up with her stage name. She chose “Billie” as an homage to Billie Dove who was a famous actress at the time, and Holiday in honor of her absentee father Clarence Holiday. And there you have it: Billie Holiday was born.

So, one night in 1933, Billie is performing in the basement of the 133rd Street Club, kicking butt, taking names, probably fending off drunk people who are falling at her feet, when all of a sudden JOHN HAMMOND (if you haven’t heard of him, he was a hot shot producer from Columbia Records. This is a huge deal. He’s worked with people like Count Basie, Aretha Franklin, Bruce Springsteen, Bob Dylan, Leonard Cohen, etc… So yeah. Big deal for the little lady) comes up and is like “Hi, you’re really talented and I want to offer you an opportunity to record with BENNY GOODMAN!!!!!!” (he probably did not shout that last bit. I just got excited. Benny Goodman is another crazy talented bandleader from the time). To which Billie probably responded “HECK YES” or something like that.

The funny thing is that this whole meeting was totally by change. Hammond was actually there that night because a famous singer at the time named Monette Moore (lol who?) was performing. However, for whatever reason, Moore canceled the performance that night and Billie Holiday went on for her instead.

Hammond made good on his promise and Holiday ended up recording her first two songs with Benny Goodman and his band: Your Mother’s Son-in-Law and Riffin’ the Scotch. Because people knew a thing or two about good music, these songs did really well, opening up the door for Holiday to perform with the likes of Teddy Wilson and Duke Ellington. People was just captivated by her soulful voice with her rich vibrato. I geek out so hard about her, you have no idea.

I obviously can’t go into every twist and turn of her music career, but I can give the highlights: She did some work with Count Basie’s band (!!!) in 1937 where she met Lester Young (!!!) who gave her the nickname that she is often called by: Lady Day (!!!!). Now, when she was working with Basie’s band, it was hoppin’. She recorded Swing Brother Swing with him, which was a pretty big hit. BUT in 1938, Holiday “left” the band on the grounds of “interpersonal differences” (I don’t wanna fan any flames, but, knowing what I know about her drug use and her fiery, stubborn personality, I think it is safe to say that she was probably fired). Don’t get me wrong, like I said, she was a crazy talented performer who had a really distinct style. But she was also known as being really unwilling to compromise that style. Which, if you’re a male musician, is fine because you have “artistic integrity” or whatever; but, as she was a lady, she was just seen as being a bitch. That’s showbiz… (Side story about touring with the Basie band: Billie was actually pretty light skinned, so when she was on TV it could sometimes look like she was white. So during one of her televised performances, the studio made her darken her skin with makeup or shoe polish because seeing a white lady performing on stage with a black band would have been too scandalous. Which is stupid and terrible and makes me mad. Holiday did not take to this kindly, either.)

After her stint with Basie, Holiday actually took a gig touring with Artie Shaw and his band. Now, Artie Shaw was particularly famous at the time, not only because he was a good conductor, but also because he was a white man. You know white people just love white musicians who appropriate black music. ANYWAY, Holiday performing with him was actually a really big deal because it would be the first time that a black vocalist (a black WOMAN, no less!) had ever been hired to perform with a white ensemble in front of people (there was some mixed recording sessions, but no one ever got to actually see those because they were in the studios). TO TOP IT ALL OFF, the band was touring around THE SEGREGATED SOUTHERN US. Big waves, people, big waves. To his credit, Shaw was apparently a really stand-up guy and when people would heckle Holiday on stage, he would turn around and tell them off. At one point, someone in charge of one of the clubs they were performing at said that Holiday couldn’t sit with the rest of the performers because she was black, and Artie Shaw gave them what for, ensuring Holiday a seat with the band. (Famous Holiday recordings from this time: Billie’s Blues, Summertime)

Holiday was a big figure as far as breaking racial barriers went. Besides being the first black musician to tour with a previously all-white band, she also had a really successful stint singing at Cafe Society, one of the rare integrated clubs at the time. This is actually where she debuted her (arguably) most famous song: Strange Fruit. A little background into the song: it’s based on a poem about a lynching written by Abel Meeropol. The song has some really profound themes dealing with racism and uses really powerful and grim imagery. At the time, her record label, Columbia, refused to let her record the song with them because it was so “political” and challenged the social hierarchy. Which, once again, is stupid. Not one to back away from a challenge, Holiday turned to the label Commodore who gladly released the song. And it was a huge hit. Here is a recording:

Alright, by this point, you’re probably feeling all warm and happy about how she’s doing such a good job and speaking out and being true to herself and her art. And now…I am afraid I must crush your spirit. This is where our story turns sour.

So, by this time, she was a huge hit, releasing famous songs like  Lover Man and You Better Go Now. Unfortunately, the pressure of fame was starting to set in. By the 1940s, Holiday was HEAVILY involved with alcohol and all sorts of drugs, from marijuana to heroin. In fact, at one point, it was reported that she was spending over half of her $1000 weekly salary to fund her heroin addiction. Her behavior became even more erratic than it had been previously and word got out that she was undependable, so she started getting less and less work coming in. In 1947, she got arrested and had to serve jail time for possession, which certainly didn’t do good things for her image. The arrest, on top of her sullied reputation, led to the revocation of her New York Cabaret Card (for those of you unaware, the Cabaret Card is a certification that allowed musicians to perform at establishments that served alcohol. So like…basically most clubs everywhere). Her income plummeted and she had a ton of trouble finding work. By the 1950s her drug use had finally taken its toll on her voice; she had lost her signature control and mastery of pitch that she had once possessed. More importantly, however, it had taken a toll on her health. In 1959, she ended up in the hospital with cirrhosis of the liver.

This is where I get really, REALLY mad. So, here she is, in the hospital, literally dying… And the cops come in and arrest her for possession of narcotics and slap a fine on her. Now, I understand that people can’t be treated differently because they are famous and being sick doesn’t give you the right to break the law or anything…but…SHE WAS LITERALLY IN BED DYING. She died in the hospital one month after her arrest at the age of 44 with only $750 to her name. It just makes me sad.

Because I think it would just be rude to leave you on that depressing note, we are going to skip back in time a little bit to talk about something less sad.

So, after her arrest in 1947, her reputation was seriously stained, but her producer at the time suggested that they have a big comeback performance at Carnegie Hall in 1987. Holiday was unsure about actually having the concert because she was afraid that no one would show up to see her, but eventually she agreed to perform. She performed to a sold-out crowd and knocked everyone’s socks off. After her huge downfall, she had one night of utter, shining bliss. (At one point during the show, someone sent her some gardenias to put in her hair because that was kind of Her Thing, but it had a hat pin in it and she didn’t see that and so she poked it into her head and bled a lot and passed out. But pretend I didn’t say that part. Let her have this shining moment)

She did a bit more recording and touring after this, but it was not nearly as good as her previous stuff because…you know…drugs and stuff. So this is where I’m stopping.

Despite her sad end, she has continued to influence people. People still buy her albums, there have been movies made about her, books written about her. Hell, just a few years ago, Ultimate Bae Audra McDonald did a cabaret style one-woman show as Billie Holiday at Emerson’s Bar and Grill (

Billie Holiday is a legend and changed the music scene forever and that should be her legacy.