In preparation for this review, I read two biographies and one extended essay on Billie Holiday. My conclusion is that it is impossible to know the real Billie Holiday. She was one of the greatest bullshitters in history.

That’s not a knock on her—she had to play the cards she was dealt at birth, a shitty hand if there ever was one. Billie figured out the game at a shockingly early age, realizing that no black woman was going to get ahead in this world through conventional career paths, which at that time pretty much meant a life of keeping house for white people. If you can’t get what you want through the rules, you have to break the rules and find another way around. She wanted action, money, sex and fame, and took advantage of every available opportunity to obtain those things, even when some of the available opportunities involved more than a touch of danger. Although shy about singing at first, she noticed that people seemed to like it in a way that seemed far out of proportion to her opinion of her vocal talents. She was sharp enough to not let her self-doubt show, riding the sound of her voice to a Harlem club gig where John Hammond heard her and arranged her first recording sessions. Over time she would become one of the greatest jazz vocalists of them all.

And that’s not bullshit.

Reviewing icons is always problematic because biographers tend to be fans and “fan” is short for fanatic. If you read Robert O’Meally’s Lady Day: The Many Faces of Billie Holiday, which focuses more on the music than the life path, everything Billie ever did was the greatest fucking thing imaginable. That’s as ridiculous as Mark Lewisohn’s assertion that “My Bonnie” by Tony Sheridan and The Beatles is one of the greatest rock ‘n’ roll records ever made. Like every other artist, Billie Holiday did not begin her career as perfection personified. She had natural talent that had to be developed and shaped by experience. She had to learn how to communicate and collaborate with jazz musicians, as collaboration is the essence of jazz. You can argue that some of her weaker stuff is better than many singers on their best days, but she had peaks and valleys just like any artist in any field. When it comes to pure vocal ability or versatility, Billie couldn’t compete with Ella Fitzgerald, but she knew how to make the most out of what little she had. What she had was a combination of presence, a deep feel for the groove and a life experience that allowed her to express the emotional subtext of the lyrics like no one has before or since.

The conventional view is that Billie Holiday’s musical career is divided into three distinct periods, roughly defined by decades. In the 1930’s, she sang swing with small combos and big bands, a singer on the rise. After “Strange Fruit” in 1939 she began to expand the role and range of a jazz vocalist and gained widespread fame. Her closing period opened after an interlude with drug addiction and legal problems and ended with a comeback assisted by the publication of Lady Sings the Blues. In that last phase, she was like the great pitcher who has lost his fastball and needs to come up with a different approach to win ballgames. Though her voice had lost color, and her limited range had become even more narrow because her drug habit had damaged her body, she found another way to use her voice to reach deep into the lyrics for hidden meanings.

This particular compilation, a “best of” sampling from the massive 10-CD Columbia set, crosses conventional lines and covers the period between 1935 and 1942. The bulk of the songs are swing standards, many of which feature cutesy-wutesy lyrics and the absurdly upbeat feel of music played over the gloom of the Great Depression. Of all the periods of jazz, the Swing Era is my least favorite, and after listening to this record over and over, I would say that Billie herself was getting tired of it towards the end of the 30’s when her growth as an artist had surpassed the lightweight songs she chose to sing.

What I love about this record is how clearly it presents the development of the artist: you can hear it as Billie gains greater control over dynamics, expands her phrasing palette and improves her give-and-take with top-tier musicians to deepen the groove and enhance melody and harmony. What pisses me off about this record is that one of her most important recordings—the original version of “Strange Fruit”—is missing because she recorded it on a label other than Columbia. I find it difficult to believe that record company executives can’t put their petty capitalist rules aside for one second to give us an accurate picture of the development of one of America’s most important artists.

Within this seven-year period are three mini-periods: the period where she developed into a true artist; the brief period towards the end of the 30s when she had outgrown traditional swing and hadn’t consistently found material worthy of her growing talent; and the miraculous stretch in 1941-1942 when she created some of the greatest recordings in music history.

Becoming the Artist

The first three numbers, all recorded with The Teddy Wilson Orchestra in the years 1935-1936, show that Billie hadn’t found her groove quite yet. Her phrasing is still too close to the score and her sense of dynamics is still undisciplined, leading to moments where she’s either too full of youthful boisterousness or delivers phrases lacking emotional content. In her defense, “What a Little Moonlight Can Do” isn’t much of a song and really too cute for Billie Holiday. On “These Foolish Things,” Teddy Wilson certainly gives her an opportunity to relax and go with the flow with his slightly offbeat and blues-tinged intro, but Billie rushes her delivery a bit and doesn’t quite click with what the combo offers. The snappy “I Cried for You” should have been a home run, but too often it sounds like she’s trying to sing over the band rather than connect with them. The one thing that is clear even in these early recordings is that the influences of Louis Armstrong and Bessie Smith ran through her veins.

The next two tracks come from her session with Artie Shaw on July 10, 1936. You can hear her starting to loosen her phrasing in the first couple of verses in “Summertime,” but what’s really remarkable is the difference in her approach after Artie Shaw’s fluid and sensuous clarinet solo. This is the moment where you can hear her shift gears and she begins to sing from her loins as well as her heart. We get the first full manifestation of Billie Holiday on the second track, “Billie’s Blues,” a song she wrote minutes before recording it. Opening like a slow boogie-woogie number, the combo shifts to New Orleans ensemble for a few measures before Billie comes in, smooth as Chambord but with more of a kick on the way down. She’s singing of her life now, and Billie’s untutored masochism in relation to men was a core aspect of her personality:

Lord I love my man, tell the world I do
I love my man, tell the world I do
But when he mistreats me
Makes me feel so blue

She really lets it rip in the second verse, messing with timing, structures, bars and rules, singing with heart and soul while tossing in a line from Blind Lemon Jefferson along the way:

My man wouldn’t give me no breakfast
Wouldn’t give me no dinner
Squawked about my supper and put me outdoors
Had the nerve to lay a matchbox on my clothes
I didn’t have so many
But I had a long, long ways to go

What happens next is something that would happen quite often in Billie’s recordings: she inspires the players to reach down inside and give it all they’ve got. In contrast to the pedestrian and trite intro, both Artie Shaw and Benny Berrigan get into this sucker and let their horns fly. When Billie gets to the last verse, she is in total command, and squeezes every bit of erotic undertone out of the autobiographical lyrics:

Some men like me cause’ I’m happy
Some calls ’em snappy
Some call me honey
Others think I got money
Some tell me baby you’re built for speed
Now if you put that all together
Makes me everything a good man needs

For some odd reason, the collection reverses time and sends us back to 1935 for “If You Were Mine,” one of her better efforts in the early Teddy Wilson sessions, but it’s still not the woman who emerged in “Billie’s Blues.” You hear that woman in “A Fine Romance,” recorded with a combo called “Billie Holiday and Her Orchestra.” This Jerome Kern song was introduced to the world by Fred Astaire and Ginger Rogers in the movie Swing Time, and it became a major hit for Fred in 1936. The difference between Fred’s version and Billie’s is more than noticeable: in Fred’s rendition, he sings about an uptight partner in a way that communicates shoulder-shrugging frustration and acceptance of the status quo; in Billie’s version, you can tell there ain’t no way she’s going to put up with a guy with a limp dick who only wants to fuck in the dark. She transforms the closing lines of the last verse into a crescendo of rising heat and frustration as she imbues her voice with a growl that’s pure tiger compared to Fred’s well-mannered kitten:

A fine romance with no quarrels
With no insults and all morals
I’ve never mussed the crease
In your blue serge pants
I never get the chance
This is a fine romance

What’s remarkable here is that Billie still manages to retain the elegance of the original, one of her unique qualities that Leonard Feather referred to as “caviar and grits.” Billie could be as coarse and earthy as any singer, but even when she’s growling, she still has that indefinable quality called class.

“Easy to Love” is more class, and her vocal here is both smooth and delightfully melodic, mingling well with Teddy Wilson’s light and nimble touch on the 88’s. That same touch opens one of my favorites, “I’ve Got My Love to Keep Me Warm,” a superb example of how Billie knew her limits and worked out methods designed to distract the listener from those limitations while enhancing the meaning of the words. The third line in each of the verses ends with the word “storm” (or, in one case, the phrase “icicles form”). The musical phrase is set up for a singer to approach the final word by either holding the single note for a measure or two or by introducing a discrete glissando, hitting individual notes on the way down to the root note. Here the note is at the upper end of her range, so holding it was out of the question, and she really didn’t have the kind of chops to pull off a discrete glissando. Instead she let the note simply fall and fade naturally, a dying portamento. It was a brilliant choice because when she goes into that downward glide, you feel the snow coming down and you shiver at the visualization of the descending icicle. There are few singers who paid more attention to the lyrics than Billie Holiday, and she was the master at maximizing their meaning and impact, even when the text doesn’t seem to give her much to work with.

“I Must Have That Man” showcases her incredible feel for the groove of a song, echoing Bobby Tucker’s comment that Billie “had the greatest conception of a beat I ever heard.” She just melts into the rhythm of this song, while retaining a keen consciousness of the meaning of every syllable she sings. When she sings the rather corny line “I’m like the oven that’s crying for heat,” you forget about the bad simile and marvel at the tone of her voice, full of tears of sexual frustration. The song is a perfect fit for her masochistic relationship with men, but not once do you hear her expressing any sense of guilt for the fact that she longs for a man who cheats on her and treats her like shit. For Billie Holiday, the sexual thrill trumped dishonesty and abuse.

One of her first of many collaborations with “Prez” (Lester Young) comes next, the godawful “Me, Myself and I.” Somehow the two manage to defy the essential silliness of the song and in the verses after the instrumental break, where they engage in a full-fledged duet, they feed off each other, finishing each other’s phrases and creating a joyous energy that is absolutely irresistible. If you want to know why Billie Holiday is a great jazz singer and an improviser of the highest order, “Me, Myself and I” is a good place to start: she blossoms in the moment and is at her best when playing with the best. The performance here also negates the argument that Billie Holiday was just a “sad song” singer; this is as light a piece as you’ll find, and she nails it.

Another thing I deeply appreciate about Billie Holiday, especially now that we’re in a period when we are bombarded with show-off singers who dazzle all the morons with their pyrotechnic vocal displays, is her essential subtlety. You listen to nearly any other version of “They Can’t Take That Away from Me” and you’ll hear overwrought phrasing and excessive emphasis on the punch line, “No, no, they can’t take that away from me.” Billie’s version is quiet, understated, and marked with the tenderness she feels for her quirky lover. The line she chooses to emphasize is buried in the third verse, but is the most important line of the song: “The way you changed my life.” Billie sounds positively joyful, almost girlish in her delivery, and her tone contrasts mightily with her subtle teasing in the rest of the song. Hers is the only version of this song I can stand, and it’s all because she knew how to use her voice to create meaning.

“Easy Living” has a nice drink-and-cigarette groove, and a long, sultry introduction courtesy of Teddy Wilson and the boys. When Billie comes in, she slides into the groove with an easy grace. She peaks here on the bridge, with an “ain’t nobody’s business but our own” response to those who judge her harshly for subservience to males. Her phrasing of the simple “for you” is the essence of loving devotion:

For you . . . maybe I’m a fool, but it’s fun.
People say you rule me with one wave of your hand.
Darling, it’s grand.
They just don’t understand.

Yes, she picked a whole lot of losers as the objects of her devotion, but it was engaging in the act of devotion that mattered to her.

“A Sailboat in the Moonlight” comes next, and while I think Billie’s on fire here, I find the combo a bit out of sync with the mood she’s trying to create . . . except for Lester Young, who echoes Billie’s rough sultriness. The same musicians are much more supportive in “Travelin’ All Alone,” especially Buster Bailey on the clarinet. Billie’s performance is prescient in that it captures the feelings of isolation, loneliness and anxiety she would experience first-hand when she traveled with Artie Shaw’s band the following year. Her tone is one of despair rather than complaint as she considers her dreary lot in life:

I’m so weary and all alone
Feel tired like heavy stone
Trav’lin’, trav’lin’ all alone

Who will see and who will care
‘Bout this load that I must bear
Trav’lin’, trav’lin’ all alone

The lyrics actually deal with how family, friends and society treat older people (“Leave you always when you’re old”), but Billie had no problem empathizing with anyone identified as an outcast by the dominant culture.

The combo really steps up on “When a Woman Loves a Man,” easing off and providing a slightly melancholy background for Billie to deliver a vocal full of empathy for women like herself who love with their hearts instead of their heads. Teddy Wilson’s arpeggios in the background are gorgeous, and Lester Young matches Billie’s mood in a lower register, deepening the melancholy. “You Go to My Head” survives the jarringly horrible line “You go to my head like a sparkling burgundy brew” primarily because Billie’s phrasing and delivery remain true to the low-level alcohol buzz feel of the song.

The Lull

Billie’s Swing Era lull, where the songs and performances are of inconsistent quality, starts with “My Man” (alternatively “Billie’s Blues” and “I Love My Man”), the most pedestrian of her submissive numbers. For reasons unknown, the piece ends with a David Rose stripper-like bash that is quite jarring. It’s followed by an alternate take of “I Can’t Believe You’re in Love with Me,” opening with a typically long swing-era intro with classic muted trumpet. Billie’s vocalizations here are clarinet-like, but she spends too much time on the same note. This song ends with the same kind of bash featured on “My Man,” so perhaps it was the bees’ knees at the time. I find it annoying.

We’re now in 1938, and in a few months, Hitler would gobble up Austria while Americans continued to hit the dance floors to take their minds off the seemingly never-ending depression. Billie’s first session that year included “The Very Thought of You,” a song Bing Crosby made famous. Her approach is sweet and sensuous, mirrored by the musicians only in Lester Young’s too-brief appearance. Several months later, as Hitler got ready to dismember Czechoslovakia, Billie finished her mini-tribute to the “Road Pictures” with her version of “I Can’t Get Started,” a Duke-Gershwin number recorded by Bob Hope. Lester Young’s lush intro grounds Billie from the start, and throughout this rather challenging number with an unusually complex chord structure, she never loses command or focus. After a brief stop before the bridge—a choice that always draws attention to the singer—Billie reaches way down low in her register while maintaining her attitude of superficial composure, letting herself go only on the last line, “Baby, but what good does it do?” The contrast between the sadness in her voice and her exaggerated social status in the lyrics tells you that this is one broad who knew that love was far more important than the who’s in/who’s out dynamic that determines social standing:

I’ve been consulted by Franklin D
Robert Taylor has had me to tea
But now I’m broken-hearted
Can’t get started with you

It’s interesting that she replaced Clark Gable with Robert Taylor in the lyrics, but this was long before Robert Taylor became a dirty rat bastard ratting on alleged Reds in the movie studios.

“Long Gone Blues” is a swing-ified version of blues, with horn harmonies that are too Glenn Miller-esque for my tastes. It’s followed by “Sugar,” one of those thoroughly forgettable swing numbers that even Billie Holiday can’t save. She redeems herself vocally with “Some Other Spring,” but the melody of this song is horribly overwrought and fails to move me. Why she did “Them There Eyes” is beyond me, a too-cute number that she had to perform without the soul-level support of Lester Young. Billie closes out that fateful year of 1939 with “The Man I Love,” one of Gershwin’s most uninteresting numbers, an ode to marriage, home and family. Despite the weak material, Billie Holiday sings this song in a voice full of regret and longing, as if beneath the tough girl persona, what she really wants is to settle down in her private love nest with a loyal, faithful man. Through her phrasing and tone, though, she makes you aware that she sees this dream life as something unattainable, and that she feels almost guilty for imagining such an absurd possibility. I find her performance of “The Man I Love” quite touching; it’s Billie Holiday at her most vulnerable. Lester Young’s solo, backed only by the rhythm section, is exceptionally supportive of Billie’s approach to the song.

The Peak

Whether it was the result of a natural artistic trajectory or an acceleration generated by the recording of “Strange Fruit” in April 1939, Billie Holiday took her game to a much higher level in the too-brief years before the AFM strike in 1942 that virtually shut down recording in the United States for over two years. During this period, she recorded vocal interpretations of the highest order, works of art that will live forever.

While Coleman Hawkins’ version of “Body and Soul” may be the most historically significant version, Billie Holiday’s take trumps his when it comes to sheer seductive power. She sings this like she’s dressed in a see-through teddy, swaying sinuously to the music, presenting a sonic picture of irresistible attraction. When she sings “I’d gladly surrender myself to you, body and soul,” you can feel her hot breath on your neck as she brushes your arm with the tips of her breasts. Hmmmmmmmm.

Again playing against the torch singer stereotype, we hear a completely different Billie Holiday in “Swing, Brother, Swing.” This is one place in the book where O’Meally does not exaggerate in the least: “Her vocal incantations excite the ensemble into supercharged rhythmical action that seems, particularly because of the use of the word brother, a highly secular version of what Winthrop Sergeant called the “rhythmo-dynamic” activity of a shout-stirred religious assembly. You can almost see and hear the dancers stomping and shuffling on the floor as she beats out the words”:

Deep rhythm captivates me
Hot rhythm stimulates me
Can’t help but swing it, boys;
Swing it, Brother, Swing.

According to O’Meally, Billie swung both ways and while submissive with men, she was dominant (and abusive) with women. This is dominant Billie, driving that band like she’s wielding a whip. As the song proceeds, she asserts herself more and more; when she returns after the instrumental passage, her phrasing is completely detached from the expected beats, hitting the spots in between to give you the feeling that the record is about to spin off the turntable.

I suppose everyone had to do Cole Porter’s “Night and Day,” including Billie Holiday. Personally, I can’t stand the song, and I don’t think Billie really gets into it until she hits the “hungry yearning burning inside of me” line. While Lester Young appears on the recording, he is almost invisible, just one of the boys in the band. What comes next is another Cole Porter number that will sound appallingly racist to modern ears, the incredibly dumb “Let’s Do It.” With lyrics like these, it’s impossible to evaluate Billie’s performance:

Chinks do it, Japs do it
Upper Lapland little Lapps do it
Let’s do it
Let’s fall in love

On May 9, 1941, Billie Holiday entered the recording studio to record two of her greatest numbers, “God Bless the Child” and “Solitude.” The first was written by Billie in collaboration with Arthur Herzog, Jr., based on a phrase her mother uttered during a mother-daughter spat over money: “God bless the child that’s got his own.” Inspired by that line, Billie wrote a song that exposes socio-economic injustice in the land of opportunity and the emptiness of the American ethic that would be described quite vividly by Kurt Vonnegut in Slaughterhouse-Five:

America is the wealthiest nation on Earth, but its people are mainly poor, and poor Americans are urged to hate themselves. To quote the American humorist Kin Hubbard, ‘It ain’t no disgrace to be poor, but it might as well be.’ It is in fact a crime for an American to be poor, even though America is a nation of poor. Every other nation has folk traditions of men who were poor but extremely wise and virtuous, and therefore more estimable than anyone with power and gold. No such tales are told by the American poor. They mock themselves and glorify their betters. The meanest eating or drinking establishment, owned by a man who is himself poor, is very likely to have a sign on its wall asking this cruel question: ‘If you’re so smart, why ain’t you rich?’ There will also be an American flag no larger than a child’s hand – glued to a lollipop stick and flying from the cash register.

Billie’s poetically economical version is just as powerful, linking economic oppression to religious oppression:

Then that’s got shall get
Them that’s not shall lose
So the Bible said and it still is news
Mama may have, papa may have
But God bless the child that’s got his own
That’s got his own

Yes, the strong gets more
While the weak ones fade
Empty pockets don’t ever make the grade
Mama may have, papa may have
But God bless the child that’s got his own
That’s got his own

Money, you’ve got lots of friends
Crowdin’ ’round the door
When you’re gone and spending ends
They don’t come no more

Rich relations give, crust of bread and such
You can help yourself
But don’t take too much
Mama may have, papa may have
But God bless the child that’s got his own
That’s got his own

Her vocal is a masterpiece, an exquisite example of disciplined phrasing and changing timbres that combine to make the subtext as powerful as the lyrics. While you can take any line from this song and marvel at her delivery, my favorite is the couplet, “You can help yourself/But don’t take too much.” On the first, her voice reaches for the heavens, reflecting the expansive myth of the American dream; in the second, her voice becomes penurious and parental with a slight touch of “gotcha” as she reveals the catch. This is one of those songs that you simply have to stop and listen to with full attention, for you are hearing the essential beauty and richness of the human voice.

She recorded Ellington’s “Solitude” at the same session, one of her most purely beautiful vocals. Billie usually didn’t hold her notes to the extent she does here, and her vibrato-less tone feels exceptionally warm, sensuous and pure. The backing is understated and reflective, with Eddie Heywood’s tasteful and limited piano runs providing most of the variation. Billie doesn’t need much from the band, as she sings this sad and wistful song as if she is in a trance, reliving a similar moment of separation from one she loved.

Too often ignored by the general public, “I Cover the Waterfront” certainly has a place in the top tier of Billie’s catalog. Recorded a few months before Pearl Harbor, I imagine this jazz standard took on special meaning for American women left behind while Johnny went off to war. Billie recorded this song fourteen times over the years, but I think this version is her best. The quality of her voice is at her peak, and she imbues this song about long-distance separation with vivid color and more than a touch of the noir. In the same session, she recorded the remarkable “Gloomy Sunday,” one of the most curious dark songs ever written. Originally a Hungarian composition (known as the “Hungarian Suicide Song”), the music was written by a guy who did indeed eventually commit suicide. The translation Billie used is anything but literal, but it does reflect a very dark and disturbing fantasy:

Sunday is gloomy, my hours are slumberless
Dearest, the shadows I live with are numberless
Little white flowers will never awaken you
Not where the black coach of sorrow has taken you

Angels have no thoughts of ever returning you
Would they be angry if I thought of joining you?
Gloomy Sunday

Gloomy is Sunday, with shadows I spend it all
My heart and I have decided to end it all
Soon there’ll be candles and prayers that are said I know
Let them not weep, let them know that I’m glad to go

Death is no dream, for in death I’m caressin’ you
With the last breath of my soul, I’ll be blessin’ you
Gloomy Sunday

Then, in the last verse, we find out the whole thing is a dream! Just like the ninth season of Dallas! My research of American kitsch indicates that Pam Ewing’s dream was not quite the weird fantasy portrayed in this song. Putting aside the fact that both composer and lyricist were top candidates for long-term therapy, Billie Holiday goes deep into her soul and manages to connect with her dark side in a compelling and oddly moving performance. Her vocal covers her entire range, and she defies expectations by making the lines sung in the higher part of the range far more chilling than the deeper voicings. Her vocal on the lines “Death is no dream, for in death I’m caressin’ you/With the last breath of my soul, I’ll be blessin’ you” eerily mirrors the romantic fantasy of shared death that has been a part of romantic literature for centuries. Billie may not have had the vocal range of Ella Fitzgerald, but her emotional power more than makes up for the deficit.

“Until the Real Thing Comes Along” is one of her better submissive numbers, and as in all her recordings of the early 40’s, her voice sounds fuller and richer. The collection ends with her interpretation of the classic “All of Me,” my favorite version of a song that nearly every jazz singer has done at one time or another. The track is enhanced with Lester Young’s rich-toned solos, which are in perfect sync with Billie’s feel for the song and seem to inspire Billie to deliver what turns out to be one hell of a finish, a combination of beautifully rhythmic phrasing and belt-out intensity.

I find it very distressing that people tend to focus more on Billie Holiday’s “troubled life” than on her contributions to music. She has been transformed into the ultimate victim, a soap-operatic character who tragically pissed her life away on abusive men and heroin. Americans guiltily adore self-destructive characters, handing Oscars to actors who portray them while secretly wishing they could drop their carefully constructed façades and burn in the forbidden delights of sin.

While it is true that Billie Holiday experienced more than her share of racism and sexism, she was an exceptionally strong woman who refused to let those barriers stop her from realizing her potential as an artist. Yes, she indulged herself in passions galore and likely paid the price for her indulgence by dying too young, but she had lots of good times in the process. Unlike most people who live their lives in terror of sin and death, Billie Holiday was not afraid to live her life to the fullest, and her essential courage is what allowed her to translate her intensely rich life experience into an unforgettable and authentic portrayal of the human spirit.