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49 free Billie Holiday trivia questions with answers — music quiz, new questions added Aug 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 49 questions with answers and explanations. Play the quiz
Q 01What was Billie Holiday's birth name?
Eleanora Fagan
Eleanora Fagan was her birth name; she took the surname 'Holiday' from her father, the jazz guitarist Clarence Halliday, and her first name from a film star she admired.
Q 02In which city was Billie Holiday born in 1915?
Philadelphia
Philadelphia: she was born at Philadelphia General Hospital on 7 April 1915 to a teenage mother who had been thrown out of the family home for becoming pregnant.
Q 03Which musician gave Holiday the nickname 'Lady Day'?
Lester Young
Lester Young, the tenor saxophonist she in turn called 'Prez', coined 'Lady Day' in the late 1930s; he had once been a boarder in her mother's house.
Q 04From which actress did the young singer borrow her stage first name?
Billie Dove
Billie Dove, a silent-film star she admired as a girl, supplied the first name; the surname came from her father Clarence Halliday, a jazz banjo player and guitarist who abandoned the family.
Q 05Which producer first heard Holiday in a Harlem club in early 1933 and arranged her recording debut?
John Hammond
John Hammond heard her at Monette Moore's Harlem club in early 1933 and called her 'the first girl singer I'd come across who actually sang like an improvising jazz genius'.
Q 06With which bandleader did the 18-year-old Holiday make her recording debut in November 1933?
Benny Goodman
Benny Goodman's band backed her on 'Your Mother's Son-in-Law' on 27 November 1933, which sold 300 copies; 'Riffin' the Scotch' a few weeks later sold 5,000 and 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 Brunswick studio groups from July 1935; the sessions were aimed at the jukebox trade and paid her a flat fee rather than royalties.
Q 08In which 1935 Duke Ellington short film did Holiday appear as a woman abused by her lover?
Symphony in Black
Symphony in Black: A Rhapsody of Negro Life (1935) gave Holiday her screen debut, singing 'Saddest Tale' as a woman knocked down by her lover.
Q 09Which of these was a 1936 hit for Holiday, taken from George Gershwin's Porgy and Bess?
Summertime
'Summertime', recorded on 10 July 1936 with Bunny Berigan on trumpet, charted at number 12; 'Billie's Blues' came from the same session.
Q 10Which white bandleader did Billie Holiday join after Count Basie fired her in 1938?
Artie Shaw
Shaw was pressured to add a white singer, Nita Bradley, with whom Holiday had to share the bandstand.
Q 11'Strange Fruit' began as a poem written by which Bronx schoolteacher under the pen name Lewis Allan?
Abel Meeropol
Abel Meeropol, a teacher at DeWitt Clinton High School in the Bronx, wrote the poem in 1937; he later adopted the orphaned sons of Julius and Ethel Rosenberg.
Q 12Lawrence Beitler's photograph of a 1930 lynching in which state inspired the poem 'Strange Fruit'?
Indiana
Indiana: Beitler photographed the lynching of Thomas Shipp and Abram Smith in Marion on 7 August 1930; the poem first appeared as 'Bitter Fruit' in a teachers' union magazine in 1937.
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 co-starred, and Holiday played a singing maid; the studio trimmed both stars' parts so the story would not credit the birth of jazz to African American musicians.
Q 22After her 1947 narcotics conviction, Holiday served her sentence at which federal prison camp?
Alderson in West Virginia
The Federal Reformatory for Women at Alderson in West Virginia held her from 1947 until her early release for good behaviour on 16 March 1948.
Q 23What did the drug conviction cost Holiday, barring her from clubs that served alcohol?
Owner Barney Josephson introduced her to the song; she said 'I opened Cafe Society as an unknown'.
Q 14Because Columbia found 'Strange Fruit' too sensitive, which label recorded it on 20 April 1939?
Commodore
Commodore, Milt Gabler's small label, cut it on 20 April 1939; it got no airplay but sold a million copies, and Holiday called it her biggest seller.
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, was the B-side and became a jukebox hit; she sang it with Prez in their famous 1957 television reunion.
Q 16What happened to Holiday's father, whose death she said 'Strange Fruit' recalled?
He was refused hospital treatment because he was Black
He was refused hospital treatment because he was Black: Clarence Holiday, a guitarist with Fletcher Henderson's band, died of pneumonia in Dallas in 1937, and she said 'Strange Fruit' always brought his death back.
Q 17'God Bless the Child' grew out of Holiday's argument with whom?
Her mother Sadie
Her mother Sadie refused her money; she stormed out saying 'God bless the child that's got his own' and wrote the song with Arthur Herzog Jr. in 1941.
Q 18Which impresario signed Holiday in 1952 and produced her Clef and Verve records?
Norman Granz
Norman Granz signed her in 1952; her small-group Clef and Verve sessions, many with pianist Oscar Peterson, make up most of her 1950s output.
Q 19Holiday's first Decca recording in 1944, and one of her biggest hits, was which song?
Lover Man
'Lover Man (Oh, Where Can You Be?)', recorded on 4 October 1944 with a string section, was her first Decca side and reached the pop top 20; it became one of her signature songs.
Q 20Holiday wrote 'Don't Explain' after catching her husband Jimmy Monroe with what?
Lipstick on his collar
Lipstick on his collar: Monroe came home with the smear and started to explain, and she cut him off with 'Don't explain'; she wrote the song with Arthur Herzog Jr. and recorded it for Decca in November 1944.
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 24Eleven days after leaving prison, Holiday sold out which venue, with a record 2,700 advance tickets?
Carnegie Hall
Carnegie Hall, 27 March 1948: the concert sold out with 2,700 advance tickets, a record for the hall, and she sang more than 30 songs over the evening.
Q 25What flower became Holiday's trademark, worn in her hair on stage?
Gardenia
Gardenias, usually white, pinned in her hair became her signature look from the late 1930s; at her 1956 concerts she stepped into the spotlight in a white gown with white gardenias in her black hair.
Q 26Which head of the Federal Bureau of Narcotics is alleged to have targeted Holiday from 1939 onward?
Harry Anslinger
Harry Anslinger ran the Federal Bureau of Narcotics from 1930 to 1962; his agents, among them Jimmy Fletcher, pursued Holiday for years, and the 1947 arrest sent her to prison.
Q 27Holiday's 1956 autobiography Lady Sings the Blues was ghostwritten by whom?
William Dufty
William Dufty, a New York Post journalist, wrote it from conversations with her; John Szwed argues it is broadly accurate but was watered down under threat of legal action, and Dufty's son Bevan was her godchild.
Q 28Holiday's 1958 Columbia album Lady in Satin featured a 40-piece orchestra arranged and conducted by whom?
Ray Ellis
Ellis also backed her final 1959 sessions for MGM; Columbia gave the album an unlimited budget.
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, a Seven Lively Arts special, aired live on 8 December 1957; Coleman Hawkins, Ben Webster and Gerry Mulligan also soloed on her number.
Q 30What did Holiday reportedly say after Prez's funeral in March 1959?
'I'll be the next one to go'
'I'll be the next one to go,' she reportedly told friends after Prez's funeral in March 1959; she died four months later, on 17 July 1959, aged 44.