Billie Holiday Trivia
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48 free Billie Holiday trivia questions with answers — music quiz, new questions added Oct 2026.
Billie Holiday trivia for jazz fans, vinyl collectors and anyone who has been stopped in their tracks by Strange Fruit. This quiz follows Lady Day from her birth as Eleanora Fagan in Philadelphia and a hard Baltimore childhood to the Harlem clubs where John Hammond heard her, the 1933 debut with Benny Goodman, the jukebox hits with Teddy Wilson, the touring years with Count Basie and Artie Shaw, and the friendship with Lester Young that gave her the nickname. It covers the songs and the stories behind them without quoting a lyric: how a Bronx schoolteacher's poem became Strange Fruit at Cafe Society, the argument with her mother that produced God Bless the Child, Lover Man and Don't Explain, the strings she demanded at Decca, the 1947 drug conviction, Alderson prison and the lost cabaret card, the sold-out Carnegie Hall comeback, Lady in Satin and the Sound of Jazz reunion with Prez. It ends with her death under police guard in 1959, and the films that starred Diana Ross and Andra Day. Questions range from easy to expert, and every answer was checked against a reference page and carries its source. If you enjoy this quiz, try our jazz legends, Ella Fitzgerald and Louis Armstrong quizzes next.
30 of 48 questions with answers and explanations. Play the quiz
Q 01Which name did Billie Holiday use as a child, before she took her stage name?
Eleanora Fagan
Eleanora Fagan took the surname Holiday from her father, the jazz guitarist Clarence Holiday, and the first name Billie from a film star she admired.
Q 02In which city was Billie Holiday born?
Philadelphia
Philadelphia, though she grew up in another city that some reference books still give as her birthplace; as a child she was sometimes left in other people's care.
Q 03Which musician gave Holiday the nickname 'Lady Day'?
Lester Young
Lester Young, the tenor saxophonist who once lodged with her and her mother, coined 'Lady Day'; she named him 'Prez', her president of the saxophone.
Q 04From which actress did Billie Holiday borrow her stage first name?
Billie Dove
Billie Dove, a silent-film star she admired, supplied the first name; the surname came from her father, Clarence Holiday, a jazz guitarist who chose his music career over the family.
Q 05Which producer heard Holiday singing in a Harlem club and arranged her recording debut?
John Hammond
John Hammond had gone to hear the better-known Monette Moore and found Holiday filling in for her; he soon wrote that she sang as well as anybody he had ever heard.
Q 06With which bandleader did the 18-year-old Holiday make her recording debut in November 1933?
Benny Goodman
Benny Goodman was talked into using the unknown singer by the producer who had discovered her; their second song together, 'Riffin' the Scotch', became her first hit.
Q 07Holiday's 1935 collaboration with which pianist produced the standard 'What a Little Moonlight Can Do'?
Teddy Wilson
Teddy Wilson led the small studio bands that cut these records quickly and cheaply for the jukebox trade; they are now counted among the classics of jazz.
Q 08Holiday sang in the 1935 short film Symphony in Black, built around which bandleader's music?
Duke Ellington
Duke Ellington's short let Holiday sing the blues as a woman mistreated by her lover; when Hollywood finally gave her a feature, New Orleans, it cast her as a maid.
Q 09Which song from George Gershwin's Porgy and Bess gave Holiday a hit in 1936?
Summertime
'Summertime' opens the opera as a lullaby sung to a baby; Holiday's record, made within a year of the Broadway premiere, took it onto the pop charts at number 12.
Q 10Which white bandleader hired Billie Holiday in 1938, soon after she left Count Basie's band?
Artie Shaw
Artie Shaw made her one of the first Black singers to front a white band, but she quit within the year after a hotel kept her from using the front entrance with the rest of the band.
Q 11'Strange Fruit' began as a poem written by which Bronx schoolteacher under the pen name Lewis Allan?
Abel Meeropol
Abel Meeropol taught English at DeWitt Clinton High School in the Bronx; he and his wife later adopted the orphaned sons of Julius and Ethel Rosenberg.
Q 12'Strange Fruit' sings of Southern trees, but the lynching photograph that inspired it was taken in which Northern state?
Indiana
Indiana: Lawrence Beitler photographed the lynching of Thomas Shipp and Abram Smith in the town of Marion in August 1930, and the poet said the picture haunted him for days.
Q 13At which integrated Greenwich Village nightclub did Billie Holiday first perform 'Strange Fruit'?
Cafe Society
Q 21Holiday's only major film role was in New Orleans (1947), opposite which trumpeter?
Louis Armstrong
Louis Armstrong played a bandleader and Holiday the singing maid who loves him, a part she resented; much of the music the two filmed was cut before release.
Q 22After her 1947 narcotics conviction, Holiday served her sentence at which federal prison camp?
Alderson in West Virginia
Alderson in West Virginia was where the court sent her for a year and a day after she pleaded guilty and asked for hospital treatment; she was released early for good behaviour.
Q 23What did Holiday's 1947 drug conviction cost her, changing where she could sing in New York?
Cafe Society staged it as her closing number: the waiters stopped serving, the room went dark except for a spotlight on her face, and when the lights came up she was gone, with no encore.
Q 14Because Columbia found 'Strange Fruit' too sensitive, which label recorded it on 20 April 1939?
Commodore
Commodore, Milt Gabler's small independent label, took the song her own company would not touch, and it became the best-selling record of her career.
Q 15What was on the flip side of the 'Strange Fruit' single, a jukebox hit credited with much of its sales?
Fine and Mellow
'Fine and Mellow', a blues Holiday wrote herself, carried the single on jukeboxes while radio shunned the protest song on the other side; in 1957 she sang it on television in a last reunion with Prez.
Q 16Holiday said 'Strange Fruit' always recalled her father's death, which came after what?
A hospital turned him away
A hospital turned him away because he was Black, and the lung illness Clarence Holiday had caught on tour killed him; she said the song 'reminds me of how Pop died' but kept singing it.
Q 17By Holiday's account, 'God Bless the Child' grew out of a quarrel over money with whom?
Her mother Sadie
Her mother Sadie had borrowed from her to run a restaurant, yet turned her down flat when she needed money herself, as Holiday told it; her parting shot, 'God bless the child that's got his own', became the title.
Q 18Which impresario signed Holiday in 1952 and produced her Clef and Verve records?
Norman Granz
Norman Granz, the promoter behind Jazz at the Philharmonic, put her back in front of small jazz groups after years of string-laden pop sessions, and together they made about a hundred recordings.
Q 19Holiday's first Decca recording in 1944, and one of her biggest hits, was which song?
Lover Man
'Lover Man' was the song she begged her new producer to record with strings instead of the usual small jazz band: 'I went on my knees to him,' she wrote.
Q 20Holiday said she wrote 'Don't Explain' after her husband Jimmy Monroe came home with what?
Lipstick on his collar
Lipstick on his collar: by her account Monroe started explaining and she cut him off, and the phrase kept running through her head until she finished the song with Arthur Herzog Jr.
Her cabaret performer's card
Her cabaret performer's card, issued by New York police, was revoked, and without it she could not sing in the city's nightclubs; thereafter she worked concert halls and theatres instead.
Q 24Days after leaving prison in 1948, Holiday made her comeback with a sold-out concert at which venue?
Carnegie Hall
Carnegie Hall, a concert stage, stayed open to her when her conviction shut her out of the city's nightclubs, and she packed it.
Q 25What flower became Holiday's trademark, worn in her hair on stage?
Gardenia
Gardenias pinned in her hair were part of the stage persona she fixed in the late 1930s: head tilted back, fingers snapping the beat, a single spotlight, and rooms that fell silent for her.
Q 26Which head of the Federal Bureau of Narcotics is alleged to have targeted Holiday from 1939 onward?
Harry Anslinger
Harry Anslinger had his agents pursue Holiday as a high-profile drug case, and she was under arrest in her hospital bed when she died in 1959.
Q 27Holiday's 1956 autobiography Lady Sings the Blues was ghostwritten by whom?
William Dufty
William Dufty, a New York Post journalist, wrote it quickly from conversations with her; Holiday later claimed she had never read the book that carries her name.
Q 28Holiday's 1958 Columbia album Lady in Satin featured a 40-piece orchestra arranged and conducted by whom?
Ray Ellis
Ray Ellis admitted he was unhappy with her singing at the sessions, and realised how great the performance was only when he heard the final mix a few weeks later.
Q 29On which 1957 CBS broadcast did Holiday sing a jukebox hit of hers in a famous final reunion with Prez?
The Sound of Jazz
The Sound of Jazz went out live; when the ailing Prez stood to play his chorus, the show's Nat Hentoff recalled, the two locked eyes, she nodded and half-smiled, and the control room was in tears.
Q 30Which rock band recorded the 1988 single 'Angel of Harlem' as a tribute to Billie Holiday?
U2
U2 cut it at Sun Studio in Memphis, where Elvis Presley once recorded, and brought in the Memphis Horns, as the Irish band worked its way through American roots music.