50 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 50 questions with answers and explanations. Play the quiz
Q 01What was Billie Holiday's birth name?
Eleanora Fagan
She took 'Billie' from the actress Billie Dove and 'Holiday' from her father, guitarist Clarence Halliday.
Q 02In which city was Billie Holiday born in 1915?
Philadelphia
Her teenage mother had been thrown out of the family home in Baltimore for becoming pregnant; Billie grew up in Baltimore.
Q 03Which musician gave Holiday the nickname 'Lady Day'?
Lester Young
She called the tenor saxophonist 'Prez'; 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
Her 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
He 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
'Riffin' the Scotch' sold 5,000 copies and became her first hit; 'Your Mother's Son-In-Law' sold 300.
Q 07Holiday's 1935 collaboration with which pianist produced the standard 'What a Little Moonlight Can Do'?
Teddy Wilson
The Brunswick 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
She sang 'Saddest Tale' in her scene.
Q 09Which of these was a 1936 hit for Holiday, taken from George Gershwin's Porgy and Bess?
Summertime
Artie Shaw played clarinet on the July 1936 session that produced it alongside 'Billie's Blues'.
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
He later adopted the orphaned sons of Julius and Ethel Rosenberg.
Q 12Meeropol's poem was inspired by Lawrence Beitler's photograph of a 1930 lynching in which state?
Indiana
He first published it 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
Owner Barney Josephson introduced her to the song; she said 'I opened Cafe Society as an unknown'.
Q 21Holiday's only major film role was in New Orleans (1947), opposite which trumpeter?
Louis Armstrong
Racism and McCarthyism led producers to trim both stars' parts so the film would not suggest Black people created jazz.
Q 22After her 1947 narcotics conviction, Holiday served her sentence at which federal prison camp?
Alderson in West Virginia
She was released early for good behaviour on 16 March 1948.
Q 23What did the drug conviction cost Holiday, barring her from clubs that served alcohol?
Her cabaret performer's card
Q 14Because Columbia found 'Strange Fruit' too sensitive, which label recorded it on 20 April 1939?
Commodore
Milt Gabler's label got no airplay for it, but the disc sold a million; 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
She later performed the same song with Lester Young on TV's The Sound of Jazz.
Q 16Holiday said singing 'Strange Fruit' reminded her of how her father died. What happened to him?
He was refused hospital treatment because he was Black
'Twenty years after Pop died the things that killed him are still happening in the South,' she wrote.
Q 17'God Bless the Child', Holiday's most covered record, grew out of an argument with whom?
Her mother Sadie
Her mother refused her money; she stormed out with the phrase that became the title and wrote the song with Arthur Herzog Jr.
Q 18Under what pseudonym did Billie Holiday record 'Trav'lin' Light' with Paul Whiteman in 1942?
Lady Day
'The Duchess' was actually her mother Sadie's nickname.
Q 19Holiday's first Decca recording in 1944, and one of her biggest hits, was which song?
Lover Man
She walked out of the first session on seeing the string section, then embraced strings, an arrangement style associated with Sinatra and Fitzgerald.
Q 20Holiday wrote 'Don't Explain' after catching her husband Jimmy Monroe with what?
Lipstick on his collar
She recorded it for Decca in November 1944 and again in 1945 with softened lyrics.
Thereafter she had to work in concert halls and theatres.
Q 24Eleven days after leaving prison, Holiday sold out which venue, with a record 2,700 advance tickets?
Carnegie Hall
Someone sent gardenias; she pinned them on and stuck the hidden hatpin into her head without noticing.
Q 25What flower became Holiday's trademark, worn in her hair on stage?
Gardenia
At Carnegie Hall in 1956 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
The claim that she was pursued specifically for singing 'Strange Fruit' originated in Johann Hari's 2015 book Chasing the Scream.
Q 27Holiday's 1956 autobiography Lady Sings the Blues was ghostwritten by whom?
William Dufty
Scholar John Szwed argues it is broadly accurate but was watered down under threat of legal action; his 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 Seven Lively Arts special aired live on 8 December 1957 with Coleman Hawkins, Ben Webster and Gerry Mulligan.
Q 30What did Holiday reportedly say after Prez's funeral in March 1959?
'I'll be the next one to go'
She died four months later, on 17 July 1959, aged 44.