Billie Holiday, one of the most influential jazz and blues singers of all time, captivated audiences with her haunting voice and emotional depth. Despite a life marked by poverty, struggles with drugs, and the harsh realities of racism, she became a Grammy-winning legend. Her powerful spirit and groundbreaking music left an indelible legacy that inspires generations.
31. A Difficult Upbringing in Baltimore (1915-1925)
Eleanora Fagan was born in Philadelphia on April 7, 1915, to teenage parents Clarence Halliday and Sarah Julia “Sadie” Fagan. Her aunt’s mother-in-law, Martha Miller, largely raised Holiday due to her mother’s frequent absences. She struggled in school, frequently skipping classes. At age nine, she was sent to a Catholic reform school, where she was traumatized after being locked up overnight with a dead girl as punishment.
30. Early Hardships and Moving to Harlem (1926-1929)
At age 11, Holiday dropped out of school to help her mother run a restaurant. In 1926, she survived an attempted rape and was placed in protective custody. After her release, she worked in a brothel, running errands and cleaning homes. During this time, she discovered the music of Louis Armstrong and Bessie Smith. By late 1928, Holiday’s mother moved to Harlem, and in early 1929, she reunited with her mother in New York.
29. Early Career and First Recordings (1929-1933)
As a young teenager, Billie Holiday began singing in Harlem nightclubs. She adopted her stage name from actress Billie Dove and her father, Clarence Halliday. In late 1932, at age 17, Holiday replaced Monette Moore at Covan’s. Producer John Hammond discovered her in early 1933 and arranged her recording debut with Benny Goodman. Her first hit, “Riffin’ the Scotch,” sold 5,000 copies.
28. Collaboration with Teddy Wilson (1935-1938)
John Hammond signed Holiday to Brunswick Records in 1935 to record swing-style pop tunes with pianist Teddy Wilson. Her improvisational style shined in songs like “What a Little Moonlight Can Do,” which became her “claim to fame.” Despite financial struggles, Brunswick found success with Holiday’s recordings, considering her a key artist.
27. Musical Partnership with Lester Young (1935-1938)
Holiday formed a deep musical bond with saxophonist Lester Young, who had boarded at her mother’s home in 1934. Their chemistry was evident in recordings, with Young describing their music as sharing “the same mind.” He nicknamed her “Lady Day,” while she called him “Prez,” reflecting their close artistic connection.
26. Singing with Count Basie (1937)
In late 1937, Billie Holiday joined Count Basie’s big band, selecting her own songs and arrangements. Despite grueling travel conditions, she performed hits like “I Must Have That Man” and “Summertime.” She was heavily involved in shaping the band’s sound, earning Basie’s respect for her musical instincts.
25. Rivalry with Ella Fitzgerald (1938)
Holiday competed with Ella Fitzgerald, who sang for Chick Webb’s band. The two groups faced off in a battle at the Savoy Ballroom in January 1938. While Metronome Magazine favored Holiday, Fitzgerald won the audience vote. Despite their rivalry, the two later became friends and respected each other.
24. Leaving the Basie Band (1938)
By February 1938, Holiday was no longer with Basie’s band. Reasons vary, with reports citing low pay, poor working conditions, and creative differences. Some claimed she was unreliable, while others suggested she refused to sing certain songs. Shortly after, she joined Artie Shaw’s orchestra, breaking racial barriers in music. Holiday became one of the first Black women to tour with a white orchestra, a groundbreaking achievement.
23. Touring with Artie Shaw (1938)
Racism plagued her experience. In the segregated South, audiences heckled her, and venues enforced discriminatory policies. Shaw defended her, and they were featured on WABC radio. Critics praised her voice, boosting her popularity. However, pressure to feature white vocalists limited her performances. Despite this, she helped Shaw’s band win multiple band battles, proving her star power in the jazz industry.
22. Facing Discrimination at the Lincoln Hotel (1938)
In November 1938, Holiday was forced to use the service elevator at New York’s Lincoln Hotel due to racist complaints. Frustrated by constant mistreatment, she left Shaw’s band soon after. This moment highlighted the racial inequalities she endured despite her immense talent and contributions to jazz.
21. Becoming a Jazz Icon (1938)
By late 1938, Holiday was a rising star. She toured with top bands, recorded hits with Teddy Wilson, and had songs like “What a Little Moonlight Can Do” and “Easy Living” imitated by singers nationwide. Her single “I’m Gonna Lock My Heart” became a pop chart success, solidifying her fame.
20. “Strange Fruit” and Its Impact (1939)
In 1939, Holiday introduced “Strange Fruit,” a haunting, anti-lynching ballad, originally a poem by Abel Meeropol. She performed it at Café Society, a groundbreaking integrated nightclub. Holiday’s label, Columbia, refused to record “Strange Fruit” due to its controversial subject. Milt Gabler at Commodore Records stepped in, and the song became her best-selling record, although it received no airplay
19. Rising to Stardom After “Strange Fruit” (1939)
Following “Strange Fruit,” Holiday’s fame skyrocketed. She became a household name, received press in Time Magazine, and demanded better pay. She continued recording with Commodore, producing hits like “I Cover the Waterfront” and “I’ll Be Seeing You.” Her version of “Embraceable You” was later inducted into the Grammy Hall of Fame.
18. Rise of “God Bless the Child” (1941)
Holiday’s mother, Sadie, opened a restaurant using money borrowed from her daughter. When Holiday needed financial help, her mother refused, leading to an argument that inspired the song “God Bless the Child.” Co-written with Arthur Herzog Jr., the song became one of Holiday’s biggest hits, selling over a million records.
17. First Capitol Records Hit (1942)
Under contract with Columbia, Holiday recorded “Trav’lin Light” for Capitol Records using the pseudonym “Lady Day.”The song succeeded, reaching No. 23 on the pop charts and No. 1 on the Harlem Hit Parade. Life magazine soon called her “the most distinctive style of any popular vocalist.”
16. Signing with Decca and Pop Success (1944-1946)
Milt Gabler signed Holiday to Decca, where she recorded “Lover Man,” one of her biggest pop hits. Holiday insisted on adding string arrangements, a departure from her jazz roots. The song’s success led to solo concerts, a rare feat for jazz singers in the 1940s, solidifying her mainstream appeal. By 1946, she re-recorded “Don’t Explain” with altered lyrics, along with “Big Stuff,” “You Better Go Now,” and “Good Morning Heartache.”
15. Hollywood and New Orleans (1946-1947)
Holiday landed a role in the film New Orleans alongside Louis Armstrong. However, racism and McCarthy-era censorship limited her screen time. Despite filming multiple scenes, most were cut. She recorded “The Blues Are Brewin'” for the film’s soundtrack but struggled with heroin addiction on set, impacting her career. By 1947, Billie Holiday was at the height of her career, earning $250,000 over three years. She ranked second in the DownBeat poll and fifth in Billboard’s annual college poll.
14. Drug Arrest and Sentencing (May 1947)
On May 16, 1947, Holiday was arrested for narcotics possession in her New York apartment. Her lawyer did not show up during her trial, leaving her feeling abandoned. She pleaded guilty and was sentenced to Alderson Federal Prison Camp in West Virginia, losing her cabaret card and ability to perform in nightclubs.
13. Early Prison Release (March 1948)
Holiday was released early on March 16, 1948, due to good behavior. Her pianist, Bobby Tucker, and her dog, Mister, greeted her at Newark station. The excited dog knocked her over, causing a scene that attracted reporters and onlookers, making her return from prison highly publicized.
12. Carnegie Hall Comeback (March 1948)
Ed Fishman, her manager, arranged a comeback concert at Carnegie Hall on March 27, 1948. Despite her fears, the concert was a massive success, selling 2,700 tickets in advance. During the show, she accidentally stabbed herself with a hatpin in her signature gardenias but still gave a stunning performance.
11. Broadway Show Success (April 1948)
On April 27, 1948, Holiday starred in Holiday on Broadway, a show arranged by Bob Sylvester and promoter Al Wilde. The show received praise from music and drama critics but closed after three weeks. Despite the short run, it was an essential moment in her post-prison career.
8. Illegal Club Performance (1948)
Holiday performed at the Ebony Club in 1948 despite losing her cabaret card. Her manager, John Levy, believed he could get her card reinstated. She was terrified of being arrested but performed anyway. The audience loved her, proving that her talent and stage presence remained as powerful as ever.
9. Second Drug Arrest (January 1949)
Holiday was arrested again on January 22, 1949, in her San Francisco hotel room. Around this time, she finalized her divorce from Jimmy Monroe and ended her relationship with Joe Guy, her former drug dealer. Her struggles with addiction continued to impact both her career and personal life.
8. Crazy He Calls Me Becomes a Hit (October 1949)
In October 1949, Holiday recorded Crazy He Calls Me, which later entered the Grammy Hall of Fame. It was her biggest hit for Decca after Lover Man. However, due to her reputation, radio stations rarely played her songs, limiting her commercial success despite strong public admiration.
7. Billie Holiday’s Struggles and Comeback (1950)
By the 1950s, Billie Holiday’s health suffered due to drug abuse, alcohol, and toxic relationships, especially with Louis McKay from the early 1950s. They married in 1957, but he was involved in organized crime and reportedly abusive. She attempted to rebuild her life, appearing on The Comeback Story to discuss overcoming past mistakes. Despite personal struggles, she continued to tour and perform, proving her resilience and lasting influence in jazz music.
6. European Tour and Musical Success (1954)
Holiday toured Europe in 1954, performing in Sweden, Germany, the Netherlands, Paris, and Switzerland. The tour, organized by Nils Hellstrom, featured other prominent jazz musicians. A live recording from Germany was released as Lady Love – Billie Holiday, capturing her powerful voice and emotional delivery that captivated international audiences.
5. Lady Sings the Blues and Carnegie Hall Concert (1956)
In 1956, Holiday released her autobiography Lady Sings the Blues, co-written by William Dufty. She recorded an album of the same name to accompany the book, featuring re-recordings of her biggest hits. That same year, she performed at Carnegie Hall, delivering an emotional and celebrated performance despite declining health.
4. Financial Struggles and Royalties Loss (1958)
The loss of her cabaret card drastically reduced Holiday’s earnings. She had never received fair record royalties; by 1958, she made only $11 from her songs. Her legal team’s poor management further hurt her finances, leaving her struggling despite being one of the greatest jazz singers ever.
3. Illness and Death (1959)
In early 1959, Billie Holiday was diagnosed with cirrhosis of the liver. Despite initially stopping drinking, she relapsed and was hospitalized on May 31 for liver and heart disease. While in the hospital, she was arrested for narcotics possession. She received her last rites on July 15 and died on July 17, 1959, at age 44, due to pulmonary edema and heart failure.
2. Her Bank Account and Burial (1959)
Holiday had been swindled out of her earnings and died with only $0.70 in her bank account. Her funeral was held on July 21, 1959, at the Church of St. Paul the Apostle, and she was buried at Saint Raymond’s Cemetery in the Bronx. Songwriter and theater producer Michael P. Grace II paid for her funeral.
1. Media and Legacy (1961-Present)
She was inducted into the Down Beat Hall of Fame in 1961, and Columbia Records reissued many of her early recordings. In 1972, Diana Ross portrayed her in Lady Sings the Blues, earning an Oscar nomination, which included Billie Holiday’s love relationship with Tallulah Bankhead in the late 1940s. Billie Holiday earned a Grammy Lifetime Achievement Award in 1973, and her album Lady in Satin won a posthumous Grammy in 1993.