Billie Holiday and Lester Young: Lady Day and Prez (2024)

In Paris, a couple of weeks before his death on 15 March, 1959, Lester Young spoke about his friend Billie Holiday. “She’s still my Lady Day,” he commented mournfully. By 13 March, suffering from stabbing pains in the stomach, he returned to New York. On the transatlantic flight, as the varicose veins in his oesophagus split, he started vomiting blood.

Surviving an agonising eight-hour trip, Lester arrived at his New York hotel, the Alvin, and resumed drinking in his room, which faced Birdland. After sinking into unconsciousness, he momentarily awoke, sluggishly moving his fingers and lips as if playing the saxophone. Then he slipped away.

At his funeral, the family of Young’s estranged wife refused to allow Holiday to perform. Close to hysteria, she muttered: “Those motherf*ckers won’t let me sing for Prez.” On top of her addiction to heroin and alcohol, his death aggravated Holiday’s fragile psyche; it was at the funeral that she confided to jazz critic Leonard Feather: “I’ll be the next to go.” She died four months later on 15 July, 1959.

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The intensely intimate but totally platonic relationship that developed between Young and Holiday from 1934 was publicly recognised during their lifetime. Aishah Rahman’s musical Lucky Day also focused on the personal and musical affinity that existed between the two. And just last year, the Afro-American poet Kamau Daaoud recorded Balm of Gilead (for Billie Holiday and Lester Young) for his album Leimert Park.

Today Daaoud explains that “their friendship arose from this common understanding of the nature of the world that they lived, and the nature of the pain they had to struggle through to do what they had to do”. Indeed, their slow physical and mental disintegration from the mid-1940s onwards was uncannily similar as they wrestled with their respective addictions, racist abuse and their unique character traits.

Billie Holiday and Lester Young: Lady Day and Prez (1)

Young, one of the most imaginative tenor saxophonists of this century, was a distressingly shy man. He disguised his delicate temperament behind a bittersweet smile. He also invented an idiosyncratic language that acquaintances sensed was another means of distancing himself from an insensitive world. This maddened one of his booking agents, who exclaimed: “I’d talk to him and all he’d say was ‘bells’ or ‘ding, ding’!” Young was the originator of the term “bread” as an expression for money, and habitually called both men and women “lady”. He was, of course, the man who nicknamed Billie Holiday “Lady Day”, and she in turn called him “Prez”. She once explained: “I always felt he was the greatest, so his name had to be the greatest. I started calling him the President.”

They met in 1934, following Young’s arrival in New York to join Fletcher Henderson’s group. Holiday invited him to live with her and her mother after he discovered a rat in his Harlem hotel. In her autobiography, she recalled that “he’d come by the joints where I was singing, to hear me or sit in”. At this stage neither of them had recorded anything, but they constantly boosted one another’s morale.

By 1937, having recorded independently of each other, they cut some startlingly elegant music together, displaying an unparalleled musical compatibility that verged on telepathy. Today George Avakian, the jazz producer who befriended both of them, believes: “The session in which she did A Sailboat in the Moonlight is really the one that expresses their closeness musically and spiritually more than any other.”

Holiday admitted she wanted to sing in the style that Young improvised, while he often studied the lyrics before playing a song. Up to 1941, they continued recording music together that was released through Teddy Wilson and his Orchestra, Billie Holiday and her Orchestra or Count Basie and his Orchestra.

In the late 30s, Young and Holiday’s relationship was perhaps at its most cohesive. They toured together with Count Basie’s orchestra, gambling on the bus and frequently drinking a mixture of port and gin that they nicknamed a “top and bottom”. They also loved smoking pot, and – with Buck Clayton – were inseparable on the tours across the States, calling themselves “the Unholy Three”.

Despite the often-gruelling nature of these trips, this was a dynamic period for Young and Holiday. The other musicians were also immensely fond of them. This included trombonist Benny Morton. Interestingly, though, he sensed that “you never got an idea that she wasn’t enjoying life, but to me this was a cover-up. The laughter, this was a top, this also goes for Lester. He was one of the nicest men I’ve ever known, so very kind, but I think he felt the world had short-changed him.” Although Holiday’s personality was more extrovert than Young’s, they were both insecure and vulnerable, traits that became increasingly pronounced in the 1940s.

Today, Kamau Daaoud suspects that “the whole drug scene, the alcohol thing which were the pacifiers for pain, it was a way of escape for these sensitive people”. Lester Young often commented that “I feel a draught” when he sensed a racist atmosphere, and his personality became radically more insular after the abuse he suffered in the US army in 1945. After three months of being drafted, he was arrested for possession of marijuana and barbiturates. But it was more likely the discovery that he had a white common-law wife that antagonised the officials and provoked a trial and subsequent sentence of 10 months in the detention compound.

Today George Avakian recalls that “it must have been crushing, [and] Lester never spoke about the experience in the army”. After his discharge, he discovered that many emerging bop musicians were praising him. But this flattery unnerved him because he sensed he was being robbed of the light, mercurial tone he had so carefully forged. Young once remarked that “they’re picking the bones while the body’s still warm”. His consumption of gin also increased.

Holiday, who famously announced that “there’s no damn business like show business, you have to laugh to keep from throwing up,” was besieged by racism and a myriad of vile, manipulative boyfriends, husbands and managers throughout her life. One unresolved dilemma seemed to precipitate another, more complex one, and Holiday undoubtedly felt conspired against. Regarding her trial for possession of heroin in 1947, she observed: “It was called ‘The United States of America Versus Billie Holiday’, and that’s just the way it felt.” Adversity upon adversity broke down her ebullient spirit. In his poem about this couple, Daaoud intones: “Gardenia floating on a sacred lake of tears, pork-pie hat flattened by the weight of the world.”

In 1951, a little surprisingly, after performing together for a week in Philadelphia, an argument between Holiday and Young resulted in neither of them speaking to each for three years. But as Daaoud stresses: “Friends do that. It happens because of the closeness.” This rift was the outcome of Young chiding Holiday over her heroin addiction and his irritation that she referred to him in interviews in the past tense, stating: “Lester was my favourite tenor player.” But the couple were reunited on stage at the very first Newport jazz festival in 1954. A journalist from Down Beat observed: “He shuffled on stage and once again was part of a Billie presentation. They later embraced in the dressing room and the feud was over.”

The merits of their respective recordings in the 50s were constantly debated over by jazz critics. A sense of vulnerability and introspection infused their music of this period, which was frequently in the shape of melancholic ballads. In 1955, Young was admitted to Bellevue hospital, following a nervous breakdown. He would return to hospital in 1957, suffering from alcoholism and malnutrition.

Billie Holiday and Lester Young: Lady Day and Prez (2)

In the late 1950s, Holiday and Young drank quietly together in bars close to Birdland and saw in one another their own deterioration staring back at them. George Avakian visited Young at the Alvin Hotel where he lived for the final year of his life. George remembers: “I think they both just got exhausted, that’s the feeling I had with both of them when I saw them in their last years. They were tired people. They were not the bright-eyed, energetic people I knew when we were all younger.”

Within two months of Young’s death, Holiday collapsed into a coma. At the hospital, a white powder was discovered by her bed. She was fingerprinted and photographed on her deathbed by the police. They also confiscated her records and comic books. She died on 15 July, 1959, with less than $1,000 in her name.

But despite the bleak nature of their deaths and the sadness that overcame them, both Holiday and Young left behind an extraordinarily beautiful body of work. Kamau Daaoud: “It’s almost like if you squeeze a heart in that pain, the nectar that drips from it is incredibly angelic, it’s sweet. It’s always that age-old question: Do you have to walk in fire to sing the songs that they did? If they’d had patron saints and were kept musicians, would the song be as sweet?”

Billie Holiday and Lester Young: Lady Day and Prez (2024)

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