Judy Garland and Billie Holiday
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In Bob Stanley’s Let’s Do It ‘The Winds Grow Colder’ for Judy Garland and Billie Holiday

In this excerpt from Bob Stanley’s history of pop music, Let’s Do It, the music and stories of iconic singers Judy Garland and Billie Holiday are forever intertwined.

Let's Do It: The Birth of Pop Music: A History
Bob Stanley
September 2022

The Winds Grow Colder:
Judy Garland and Billie Holiday

More than anyone else in this book, [Let’s Do It: The Birth of Pop Music] Judy Garland and Billie Holiday seem relatable to twenty-first-century pop. They have permanence. Holiday’s slightly-behind-the-beat wooziness may well have been the single most important influence on female singers of the last two decades. Garland’s blend of blow-the-roof-off talent and insecurity – ‘I can sing! Wanna hear me? Is that OK?’ – has correlated to the new century’s TV talent-show winners. They are also modern totems because of the grimness of their pre-fame years, their dysfunctional upbringings, and because of how they were first abused by men, then used by the entertainment industry’s machinery, before being left out in the rain, dying without the final act they deserved. Both have wisdom in their voices (an illusion, of course). Both were thoroughly tuned in to the songs they were singing. Both had the touch of the universal. Both made singing sound so easy early on; they made living seem so easy – the cushion of fame, the precious ability to convey real joy – and then they made it seem so tough, so impossibly tough that they couldn’t take it.

Musicals didn’t need a link to Vienna, a Jeanette MacDonald or a Howard Keel, to be valid. Judy Garland’s delivery was unrelated to opera, or operetta, or jazz for that matter; she was pure pop, a star with pipes who could walk onto a stage or appear on a screen and everyone looking at her immediately felt better. She was no one’s idea of a rebel.

The last film that she made as a child, The Wizard of Oz, found her singing the Harold Arlen and Yip Harburg song ‘Over the Rainbow’, which would become a frozen moment in popular culture; three decades later, it would also be the last song she ever sang in public. Even in 1939, aged just seventeen, she said the song made her feel ‘like a grandmother in pigtails’.

She had been in pigtails – and a rustic smock, living on a melon farm – in her very first film, 1936’s Pigskin Parade. It was one of many inter- changeable ‘college’ musicals that Hollywood turned out in the decade following The Jazz Singer, a forerunner of the 1960s beach movie, and fourteen-year-old Judy got to sing a few songs of her own (none of which was as good as the film’s highlight, Tony Martin’s ‘You’re Slightly Terrific’). Her presence and her voice were so instantly infectious that songs were shoehorned into her next few movies: in Thoroughbreds Don’t Cry (1937) she started off playing a Chopin piece, then ragged it; Everybody Sing (1938) was essentially a screwball comedy with a bunch of Judy songs thrown in because they made the second-rate script fizz. She didn’t come from jazz, but in Everybody Sing she was the embodiment of the swing era’s energy: ‘Mr Mendelssohn’s had his day,’ she sang, ‘Benny Goodman is here to stay.’ Judy’s character was expelled from school for her troubles: ‘You’ve corrupted this school for the last time!’ squawked her headmistress. Judy Garland was youth, America’s future, and here, she said, was the music to prove it.

Deanna Durbin had previously been MGM’s musical star. Apple-pie pretty, Durbin was not an obvious force for conservatism, but her light operatic voice sounded as stuffy as a Chesterfield compared to Garland’s. They appeared together in a short called Every Sunday, just before Garland’s star rose with Pigskin Parade, and Durbin left MGM for Universal. Their styles are complementary, but one is singing in Italian, a remnant of the old world, while the other soars skyward, more a Western Air Express than a nightingale.

In 1935, having just turned thirteen, Garland had sung ‘Broadway Rhythm’ on the Shell Chateau Hour, hosted by Wallace Beery, who asked her, ‘What do you want to do when you grow up to be a great big girl, huh?’ It’s easy to forget that, as a child star, there was a more or less copper-bottomed guarantee that she would be washed up at sixteen. Judy at this time was one of a string of Hollywood child stars, with Shirley Temple at the top of the tree and Bobby Breen just behind. The difference was that she did not sing ‘On the Good Ship Lollipop’ – it would have seemed ridiculous. Like Brenda Lee in the 1960s (who was just thirteen when she raspily sang of her know-how on ‘Sweet Nothin’s’), or Michael Jackson at the turn of the ’70s, Judy sang adult songs, always. Unlike the frighteningly whisky-aged Brenda, she had a voice that blended childish fear and teenage insecurity with zeal, and the assurance to make it relatable to all ages.

Her singing always felt spontaneous, as close to ‘free’ as anyone mentioned in this book; the word you want to use is ‘innocent’, though you also want to wince as you say it. Garland’s style was warm, both shy and aggressive, artless even, the polar opposite of Peggy Lee (who had an equally limited range but patrolled it like a hawk), and the likely reason for this – as with every other aspect of her life – was that her approach had been frozen as a child. Listen to something as ebullient as ‘The Trolley Song’, and you hear both a child’s enthusiasm for singing and an odd wisdom. Garland was aware that this was what people liked in her voice, and so she never really lost this naivety, hanging on to it in spite of everything. It helped to make her ballad-singing in the 1950s and ’60s, by then freed from her destructive MGM contract, all the more powerful. You had all this and you lost it? And no one cared? It was often a tough listen, but it won her an adoring audience of outcasts, even as her voice failed and her vibrato became like an off-centre record. Jerry Lewis said that ‘all the people whose insides have been torn out by misery identify with her’. And, of course, there were plenty of fans who still thought of her as Dorothy, even after she turned forty, and were surprised that she didn’t appear in red Mary Jane slippers. Derek Jewell of the Sunday Times wrote of a live performance: ‘She walks the rim of the volcano each second. Miraculously she keeps her balance. It is a triumph of the utmost improbability.’

What else do we hear in her voice, in happier times? Jolson’s eagerness to please is in there, but it never overpowers. Some of Jolie’s nasal sound too, and his bowing of words (‘Rock a booyyye your baby’). Sadness was already there: take the self-referencing ‘Play That Barbershop Chord’, from 1949’s In the Good Old Summertime: ‘When you start that minor part, I feel your fingers slipping and gripping my heart.’ Who could she have had in mind? In 1941, aged nineteen, she had been engaged to composer David Rose, who later went on to write ‘The Stripper’, the bawdiest piece of music ever written. But Judy began seeing song-writer Johnny Mercer; she married Rose in a bid to squash the affair, but it didn’t work. Mercer wrote ‘I Remember You’ about her, first sung by Dorothy Lamour in The Fleet’s In (1942), but best remembered via Frank Ifield’s yodelling 1962 UK number-one hit: ‘When my life is through and the angels ask me to recall the thrill of them all, then I will tell them I remember you.’

By the turn of the 1950s Garland had been dropped by MGM, having played the lead in twenty-three movies in fifteen years and suffering a nervous breakdown in 1949. There’s gratitude for you. When she was nineteen and still seen by MGM as a child star, the studio and her mother had arranged for her to have an abortion, to save her career. She was married at the time. By 1950 her second marriage, to director Vincente Minnelli, was falling apart, and still Louis Mayer wanted her to play a cheerleading ingénue. So Garland returned to her vaudeville roots and reinvented herself on the stage as a singer. The turning point was a run of shows at the London Palladium in April 1951, landmark live performances which she referred to as ‘an autobiography in song’.

Thanks to the gossip-greedy media, the drugs, the breakdowns and the attempted suicides would all be played out in full view of the cameras. To the public, she became the opposite of her MGM self, though the sadness had always been there. One film – after four whole years off the screen – combined the new and the old Judy Garland: 1954’s A Star Is Born. Its hit song was ‘The Man That Got Away’, with Ira Gershwin’s lyrics over a blue Harold Arlen melody that rolled like a boulder being slowly pushed up a muddy hill – the complete opposite of the grace, ease and lightness of a George Gershwin song. Ira may well have been writing about life after his brother – ‘The road gets rougher, it’s lonelier and tougher’ – and, maybe not coincidentally, he retired from songwriting almost immediately after A Star Is Born.

Instead of her most frequent co-star, potato-head Mickey Rooney, featuring alongside Garland on screen was James Mason, an actor with a velvet voice who could turn on a sixpence, his eyebrows switching from an amused pair of French accents to thunderous. He’s such fun one minute, a violent drunk the next. And as such, he’s the perfect foil for the sharp contrasts in the Judy Garland story, the black and the white, the dippy and the doomed.

Mason talked about her with his measured Hollywood-via- Huddersfield manner: ‘There’s the school of thought that believes that the bosses at MGM were the real villains because they encouraged her to take uppers and downers and get into these bad habits. And I think that’s probably true. Anyhow, she was a unique instance of a girl who had lived a most unsavoury and unhealthy lifestyle, shall we say, and therefore was a girl who was disinclined to discipline, and she could get into terrible depressions. But she wasn’t typical in any way. I thought she was wonderful. I adored her. Everybody knew about Judy, we all knew about Judy, but instead of getting one hundred percent behind her and just trying to do the best, there was an awful lot of bitching and complaining.’

After they’d shot the final scene of her final film, I Could Go on Singing, at Shepperton, Judy paused, looked at director Ronald Neame and his crew, and said, ‘You’ll miss me when I’m gone.’ Then she walked away.

In 1962 Garland released her final studio album. The late 1950s had seen her on Capitol, in the company of Nat Cole, Peggy Lee, Dean Martin and Frank Sinatra: there had been 1957’s graceful assemblage of torch songs, Alone, arranged by Gordon Jenkins; 1958’s terrific, upbeat, Nelson Riddle-led Judy in Love; and there was a fascinating oddity in the 1959 concept album The Letter, written and arranged by Jenkins, with narrative interruptions from actor John Ireland. From this point sales dipped, Garland wasn’t given the top-notch arrangers any more, and 1962’s The Garland Touch had to be pieced together from random sessions. Recordings of her final London shows show that despite received wisdom – and given that she was approaching fifty – her voice stayed strong to the end. Everything else, though, had been disappearing slowly. By the time she died in 1969 Judy Garland was stick-thin, her speech was slurred and her film and recording careers had gone completely. Her relentless optimism had finally left her.

She admitted that her life had been a hard one. ‘Do you know how difficult it is to be Judy Garland,’ she asked in Parade, ‘and for me to live with me? I’ve had to do it. What more unkind life can you think of than the one I’ve lived?’* The great movie musical effectively died with her. What was left? Cabaret, starring her daughter, Liza Minnelli. (*Her afterlife has been very different, beginning with the day of her funeral in Manhattan, on 27 June 1969. The streets were lined with fans, many of whom were gay and weren’t used to being visible in numbers. There was an energy in the air. The riots and protests that began at the Stonewall Inn later that night became a rallying call for the gay rights movement. It was her final encore and her final triumph.)

Billie Holiday could counter that with a litany of horrors. Garland had been fed sleeping pills by her mother – ‘the real Wicked Witch of the West’ – from the age of ten to help her sleep while on the road. Holiday’s great-grandmother had told her in detail about life as a slave; she grew up with a cousin who beat her; aged ten, she was raped by a neighbour; she left school at twelve and travelled to New York alone, where she worked as a maid and then as a prostitute, which landed her in jail. It is understandable that she is remembered, like Garland, as a victim. Both of their names have been used, and abused, as shorthand for self-destruction, but instead let’s look at why Holiday’s life was so special.

There is one significant stylistic difference between Judy Garland and Billie Holiday: Garland epitomised the singer who asks what a song can give her, while Holiday only considered what she could give to a song. She inhabited the song, personalised it and internalised it to a degree that no one had done before, and in this way she influenced the very biggest names who came after her – Frank Sinatra, Peggy Lee, Elvis Presley. Like Bing Crosby, Holiday wasn’t just a jazz singer, she was a jazz musician; as an innovator – though not a virtuoso in the usual sense – she was still the equal of the era’s best instrumentalists. What’s more, unlike Bing, she got to perform with these instrumentalists on a regular basis.

It’s safe to say that John Hammond had a more high-concept vision of the artists he was working with than they generally had for themselves, and Holiday fell into this category. Her debut recording – in 1933, aged eighteen – was on Benny Goodman’s daffy ‘Your Mother’s Son-in-Law’; it’s a flapper frippery, and Billie’s singing is straighter and more girlish than you would expect, but straight off her voice grabs you with its grit and occasional crack. Pianist Teddy Wilson, who never liked her voice, likened her to a female Louis Armstrong, by which he meant she was unoriginal. The public thought Wilson had a tin ear, and by 1946 she was billed as ‘America’s No. 1 Song Stylist’.

Wilson was, nonetheless, one of the most important musicians in the Billie Holiday story. Back in 1935 Hammond had talked Brunswick into recording some sides with Wilson, after Fats Waller’s small-group 78s had started clogging jukeboxes nationwide. Wilson was a far more elegant player, a musical descendant of Earl Hines who softened the Hines sound with a gentler left hand, becoming, unwittingly, the forefather of cocktail jazz. Where Hines was earthy, Wilson was genteel, propulsive but polite. Between 1935 and 1942 he recorded some three hundred understated but cool, controlled sides for Brunswick, which featured stellar singers like Ella Fitzgerald, Lena Horne and Billie Holiday. When they first recorded together, Wilson was twenty-two and Holiday twenty. Her voice was pretty, and higher than we would become used to, but already the sensuality was there. The jukeboxes were happy to have these records.

The other key figure on Holiday’s best records was horn player Lester Young; they had played together in Count Basie’s band. Young called everyone ‘lady’, male or female, and pioneered the classic post-war jazz look with his pork-pie hat. He had been a boarder at Holiday’s moth- er’s house in 1934, and he and Billie were musical soulmates. ‘I think you can hear that on some of the old records, you know,’ Young later reminisced. ‘Some time I’d sit down and listen to them myself, and it would sound like two of the same voice.’ He nicknamed her ‘Lady Day’, and she called him ‘Prez’.

Wilson, Holiday and Young improvised in the studio, which saved A&R man Hammond and Brunswick Records a bundle in arrangers’ fees. These were Tin Pan Alley songs, not Broadway, but still Wilson and Holiday spun gold, creating swing hits and jazz standards: Richard Whiting and Leo Robin’s ‘Miss Brown to You’; Benny Goodman, Irving Mills and Edgar Sampson’s ‘If Dreams Come True’; Harry M. Woods’s ‘What a Little Moonlight Can Do’.* (*A Massachusetts-born sometime London resident, Woods was the epitome of the Tin Pan Alley backroom boy, the kind that is almost entirely forgotten today. He had written ‘What a Little Moonlight Can Do’ in 1934, when he was contracted to Gaumont British Studios, but he had been a hit-maker since 1926, when his ‘When the Red, Red Robin (Comes Bob, Bob, Bobbin’ Along)’ was recorded by Whispering Jack Smith, Cliff Edwards and Al Jolson. His other major hits included Annette Hanshaw’s ‘We Just Couldn’t Say Goodbye’; ‘Side by Side’, a 1927 hit for Cliff ‘Ukulele Ike’ Edwards, but a bigger one for Kay Starr in 1953; ‘I’m Looking Over a Four-Leaf Clover’, performed by everyone from Coleman Hawkins and João Gilberto to Porky Pig; and ‘Try a Little Tenderness’, also written in London (with Britons Jimmy Campbell and Reg Connelly) and first recorded by Ray Noble, but revived in 1966 by producer/arranger Isaac Hayes and singer Otis Redding.)

A couple of years later, Holiday was enjoying a cold drink with Artie Shaw, who told her that he’d had the idea of putting clarinet and drums front and centre, but wanted ‘something sensational to give it a shove’. ‘That’s easy,’ said Holiday. ‘Hire a good Negro singer.’ For Shaw’s all-white band, in 1938, that took a lot of courage. Holiday had sung with unknown black pianists, then with Teddy Wilson and Count Basie, but this move would put her in the public eye, especially when Shaw wrote the sumptuous, seductive ‘Any Old Time’ (‘and any place where you may be’) for her.

That summer Shaw played at the Ritz-Carlton in Boston, and its white audiences became avid Billie Holiday fans. Other venues still wouldn’t let her appear, though, and Billie had to sit on the bus as Helen Forrest sang the songs Shaw had arranged for her. Eventually, after being told by one hotel that she’d have to use the freight elevator, she quit.

She fell into the welcoming arms of Café Society. This was the first integrated club in New York – the name was a joke – and had been opened by shoe-shop salesman Barney Josephson in 1938 to highlight black talent and allow black people to enjoy it; he had borrowed the idea from European cabaret clubs. This was where Holiday developed her trademark look – head tilted back, gardenias in her hair – and debuted two of her signature songs, ‘God Bless the Child’ and ‘Strange Fruit’. Columbia wouldn’t record the latter. They were afraid of their southern dealers – they didn’t want trouble with their distribution – and it ended up on a new independent jazz label called Commodore in 1939. The song itself had started life in 1937 as a poem, written by a school teacher and openly proud communist called Abel Meeropol. He approached Josephson and personally explained to Holiday why the harrowing song would be given maximum impact by her languid but powerful delivery. Holiday was blown away, and told her band, ‘Some guy has brought me a hell of a damn song.’

Unsurprisingly, ‘Strange Fruit’ was not an instant number-one hit – a song about lynching wasn’t anyone’s idea of entertainment. ‘Southern trees bear strange fruit. Blood on the leaves and blood at the root.’ It made people feel sick or angry. One man hastily wrote a note at the end of a show – ‘Here’s some strange fruit for you’ – and handed her a drawing of genitalia. Another evening, a woman followed Billie into the powder room. She was crying. ‘Don’t you dare ever sing that song again,’ she said, ‘don’t you dare.’ She then told Billie that when she was seven or eight years old, she had witnessed a lynching.

* * *

It wouldn’t be until 1946 that Billie Holiday, aged thirty-one, was offered her first film role, in a movie about the last days of Storyville called New Orleans. One look at the cast – Holiday, Louis Armstrong, Woody Herman, Meade ‘Lux’ Lewis – and the shooting on location might lead you to think it was something special. But, no: Billie played a maid. 1946 was the year McCarthyism began making its presence felt in Hollywood, and producer Jules Levey and writer Herbert Biberman were under pressure to avoid looking too liberal, and that included suggesting black people might be responsible for the creation of jazz. They needn’t have bothered: Biberman was imprisoned anyway, a year later, as one of the ‘Hollywood Ten’.

Not long after, the authorities came after Billie, and she spent nine months in prison for possession. When she came out and played Carnegie Hall in 1947, the voice was still there, nothing about her drink and drug intake was affecting her performances, but a condition of her release was that she couldn’t play in clubs with a liquor licence, just in the big theatres that didn’t serve booze. They were cutting off her oxygen.

Britain in 1954 wasn’t as proscriptive. When her microphone failed at the Manchester Free Trade Hall, she walked to the front of the stage and sang ‘My Man’ unaccompanied, to wild applause. In London, she shopped at Simpsons, bought a ski suit and knitted cap, then crossed the road to the Studio Club in Swallow Street, where she could drink triple brandies with Cointreau floats without the cops breathing down her neck. She said that she never went to people’s houses to socialise because ‘the drinks don’t come fast enough, honey, and you can’t leave when you want to’. When she played at the Royal Albert Hall on Valentine’s Day, the reception was so warm, the appreciation of her voice so great, that she seriously considered moving. ‘I want to settle in Britain, because I love the people,’ she said. ‘They call me an artist, not just a singer.’

You have to wonder what might have happened if Billie Holiday had moved to London. An album with Tubby Hayes? A role in Anthony Newley’s The Roar of the Greasepaint? A duet with Dusty Springfield on her TV show? But she stayed in New York. As a young singer, Maya Angelou saw Billie in her audience one night. She pointed her out, called her a ‘great person’, and had the crowd on its feet applauding. But during her next song, ‘Baby, Please Don’t Go’, Holiday stood up and started shouting at her: ‘Shut that bitch up. Shut up! You remind me of my mother. Shut up!’ After the show, Angelou walked up to her and confronted her: didn’t she understand how much the audience loved her? ‘No,’ said Billie. ‘They just wanted to see a black woman who’d been in trouble for drugs. That’s the only reason they look at me.’ The conditions of her death in 1959, aged forty-four, were so appallingly cruel it beggars belief. Suffering from cirrhosis, she had been under arrest in a bed at Harlem’s Metropolitan Hospital for five weeks, after police found a small amount of heroin in her room; books, her radio and record player, even flowers had been confiscated. She had been fingerprinted without her consent.

Holiday’s final album, Lady in Satin, is not unlike Marianne Faithfull’s celebrated, post-heroin Broken English. Some would say there’s a whole life in that voice; others hear a desiccated croak. It was certainly a lived-in voice, but who else would want to live there, or even stay over? I’d prefer to hear someone’s life without the inevitable downturns, the misery, the cobwebs, the clutter, the years of ingrained dirt you can never scrub away. I’m kind of glad that no one got Judy Garland into a recording studio after 1962. ‘Meet Me in St Louis’ and ‘Did I Remember’, ‘Over the Rainbow’ and ‘God Bless the Child’, ‘The Man That Got Away’ and ‘That Old Devil Called Love’ – these are clear high points of twentieth-century culture.

Reprinted with permission from Let’s Do It: The Birth of Pop Music: A History, by Bob Stanley. Published by ⒸPegasus Books All Rights Reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher. [Note: Minor layout modifications have been made to the asterisked text to accommodate online publishing.]

Bob Stanley, the author of the acclaimed Yeah! Yeah! Yeah!: The Story of Pop Music from Bill Haley to Beyoncé, has worked as a music journalist, DJ, and record-label owner, and is the cofounder and keyboard player for the band Saint Etienne. He lives in London.