Bitter Crop: The Heartache and Triumph of Billie Holiday's Last Year

“The author calls Billie ‘the consummate performer whose gift was her ability to make a listener experience the emotion she was feeling as she sang a song.’”

Jazz Singer Billie Holiday (1915–1959) was enormously popular in the 1930s and 1940s, then faced legal troubles and drug abuse that plagued her until her death. In Bitter Crop, Paul Alexander, author of earlier biographies of Sylvia Plath and J.D. Salinger, details the “perennial hardships” of Lady Day’s life but argues that she finally triumphed as one of America’s greatest singers.

His engrossing and moving book—the first biography of Holiday in some 20 years—focuses on the events of 1958 while exploring extensively her rise from a childhood in Baltimore’s red-light district. Her parents were unwed teenagers, her mentors were bordello madames.

Holiday spent hours listening to Bessie Smith, and honing her own singing skills, in the whore houses.

As a teenager, she sang in Harlem clubs. One night in 1933, producer John Hammond heard her singing at Covan’s, a club on West 132nd Street. He arranged for Holiday to make her recording debut at age 18 with Benny Goodman. She would later work with Count Basie and Artie Shaw. As a vocalist for Shaw, she became one of the first Black women singing with a white orchestra and toured the segregated south, where she often faced racism.

She soon became an established recording artist, with her songs “What a Little Moonlight Can Do” and “Easy Living” earning places as jazz standards. Her popularity was reflected by high rankings in polls taken by DownBeat and other music magazines.

Over the course of her career, she would tour in Europe, star in a Broadway show, and publish a bestselling autobiography, Lady Sings the Blues, ghostwritten by William Duffy, a New York Post writer, and filled with Billie’s familiar fabrications about her earlier life.

By 1958, after years of drinking and abusing narcotics, the singer was in “precipitous decline,” suffering from cirrhosis of the liver and ignoring doctors’ advice to quit her heavy drinking. Consumed by self-doubt when performing, she drank gin to get through sessions, Alexander writes.

Straight gin—”Gordon’s gin, her old standby”—cut her hunger for heroin.

The author details her shabby treatment throughout her career. Men often sought to take advantage of her. Louis McKay, her husband and manager, a Mafia “enforcer,” was “horrible to her, did not love her, and was there for the money,” according to one of Holiday’s close friends. (She often found solace in the loving arms of women.)

Mistreatment even extended to the news media, especially Time magazine, which never failed to delight in her frequent appearances in courts on narcotics charges. Although beloved within the jazz community and by fans, Billie was “routinely marginalized” by critics.

They “pointed out that she was untrained as a musician, could neither read nor write music, and enjoyed a grammar-school education that had progressed no further than the fifth grade,” writes Alexander.

He continues: “Her detractors wanted to portray her as unread [she enjoyed comic books], uncouth, and unworthy of her fame. Their goal was to depict her as a drug addict who never rose above the trappings of a troubled and impoverished youth in Baltimore that was defined by an unstable home life, truancy as a child, and prostitution as a teenager, all of which she acknowledged. . . . She did so in part because Billie did not view herself as a victim.”

“What she really felt, the Rosebud to understanding her, was that her life was a triumph,” said a friend.

“And it was a triumph,” writes the author.

She “had become a vital force in the entertainment industry,” traveling extensively, working with prominent members of her generation, fraternizing with leading figures in show business and politics.

“She projected an aura of style and sophistication,” says Alexander. “She was the personification of dignity and class, which she achieved despite efforts made by her enemies to tarnish the image she crafted for herself.”

He quotes the composer David Amram: “There was an elegance about her. Compared to some of the rough characters in her life, she somehow was able to rise above that. She knew that she deserved better; she understood how terrific she was. She wasn’t an egomaniac or conceited; she just knew her own worth. She carried herself like a lady. It was something she had become. She appreciated her value and the beauty of her music.”

Undoubtedly a champion of Holiday, Alexander takes pains to note aspects of her life and career that put off her detractors. Her favorite word was “motherfucker.” She was not above taking a slug at people who provoked her. And she did not hide her dismay at the painful discrimination she experienced under the Jim Crow laws of the south.

In fact, Billie continued singing the powerful anti-lynching protest song “Strange Fruit,” which she made famous in 1939–40 as a headliner at Cafe Society, an integrated nightclub in Greenwich Village, despite government warnings to stop. (FBI director J. Edgar Hoover feared “Strange Fruit” would cause discontent among African Americans and others.)

It was then that the FBI put Billie under surveillance.

When she refused to stop singing the song, “the government launched a vendetta against her, which resulted in a drug bust in 1947 that landed her in prison,” writes Alexander. Sentenced to a year and a day in prison in Alderson, West Virginia, she was released for good behavior after nine months, which sparked “a protracted campaign of harassment by the government that continued for the next decade.”

The drug possession conviction led to her losing her New York City Cabaret Card, preventing her working anywhere that sold alcohol. The effect was to deprive Holiday of gigs in high-paying New York nightclubs. She subsequently performed in concert venues and theaters.

As singer Annie Ross told the author: “’Strange Fruit’ was a factor in why they went after Lady Day, but the greater reason was that she was successful, and people loved her and they loved her singing. She had to be brought down a notch.”

The author calls Billie “the consummate performer whose gift was her ability to make a listener experience the emotion she was feeling as she sang a song.”

As a writer, he, too, is a stellar performer, using his considerable writing skills to help readers experience the emotional tenor of Holiday’s turbulent life. His book is quite special—authoritative, highly readable, and filled with vivid scenes.

Toward the end, when she was in critical condition in Knickerbocker Hospital, a private facility in Manhattan, where she was admitted smelling of alcohol and with needle track marks on her arm, Billie was visited by an old friend. “I can’t tell you how much I love [the album] Lady in Satin,” Frank Sinatra told her.

Years before, she had taught Sinatra phrasing when he was breaking away from singing with big bands. “I may have showed you how to bend a note, Frankie,” she said. “That’s all.” He always credited her as being a major influence on his career.

She died at Knickerbocker, at 44, but not before she was arrested in her hospital bed by police. “Billie Caught with Heroin in Hospital” was the predictable headline in one New York paper.

No one was more devastated by her death than Sinatra, writes Alexander. He was “inconsolable,” crying and drinking for two days in his Manhattan apartment.