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50 free 1940s Music trivia questions with answers — music quiz, new questions added Aug 2026.
43 free 1940s Music trivia questions with answers. The 1940s began with the big bands at full volume and ended with crooners, bebop and honky-tonk taking over. This quiz covers the whole decade: Glenn Miller's gold record and his disappearance over the Channel, Frank Sinatra and the bobby soxers, Bing Crosby recording White Christmas in eighteen minutes, the Andrews Sisters, Ella and Billie, the recording strike that silenced the studios for two years, Charlie Parker and Dizzy Gillespie inventing bebop, Hank Williams' six Opry encores, Vera Lynn, Rodgers and Hammerstein's Oklahoma!, and the arrival of the LP and the 45. Easy questions ask who sang White Christmas and what instrument Benny Goodman played; the hard ones want the Trinidadian lyricist behind Rum and Coca-Cola, the label that gave Nat King Cole his start and the summer that produced The Christmas Song. Written for swing fans, jazz nerds, seniors' groups and anyone whose grandparents danced to In the Mood. Every answer was checked against Wikipedia's articles on the artists, songs and events, and each question carries the sentence that backs it up.
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Q 01What record does Bing Crosby's 'White Christmas' hold?
Best-selling single of all time
Estimated sales top 50 million physical copies. He recorded it for Decca in 1942 in about eighteen minutes.
Q 02Which songwriter wrote 'White Christmas' for the 1942 film Holiday Inn?
Irving Berlin
It won the Academy Award for Best Original Song, and the industry realised for the first time that Christmas was a market of its own.
Q 03Glenn Miller received the first ever gold record in 1942 for a song about a train to which city?
Chattanooga
RCA Victor presented it for 1.2 million sales. The song was the number one record in America on the day Pearl Harbor was attacked.
Q 04Which tune was Glenn Miller's theme song?
Moonlight Serenade
He wrote it himself. His band's other hits included In the Mood, Chattanooga Choo Choo and Pennsylvania 6-5000.
Q 05Glenn Miller went missing in December 1944 when his plane vanished over which body of water?
The English Channel
He was flying from England to France for a USO show in a small Norseman aircraft. An inquiry blamed weather, mechanical failure and human error.
Q 06Glenn Miller's 'In the Mood' was based on which earlier composition by Wingy Manone?
Tar Paper Stomp
Miller's 1939 recording was later put in the Grammy Hall of Fame and named one of NPR's 100 most important American musical works.
Q 07Frank Sinatra left Harry James's band in November 1939 to sing with which bandleader?
Tommy Dorsey
He replaced Jack Leonard as lead singer, and their 'I'll Never Smile Again' spent 12 weeks at number one in 1940.
Q 08What were the teenage girls who mobbed Frank Sinatra in the early 1940s called?
Bobby soxers
They revealed a whole new youth market for pop music, making Sinatra arguably the first teen idol.
Q 09What is the chaos of 35,000 Sinatra fans locked outside New York's Paramount Theatre in October 1944 called?
The Columbus Day Riot
Only 250 people left after the first show, so the crowd outside could not get in. He was nicknamed 'Swoonatra' and 'The Voice'.
Q 10What nickname, also the title of his 1946 debut album, was Sinatra given in the 1940s?
The Voice
The Voice of Frank Sinatra reached number one on the Billboard chart. 'Chairman of the Board' and 'Ol' Blue Eyes' came later.
Q 11Bing Crosby won the Academy Award for Best Actor for which 1944 film?
Going My Way
He played a young priest, and 'Swinging on a Star' from the film won Best Original Song too.
Q 12How many Academy Award-winning songs did Bing Crosby introduce over his career?
Four
They were 'Sweet Leilani', 'White Christmas', 'Swinging on a Star' and 'In the Cool, Cool, Cool of the Evening'.
Q 13How many Andrews Sisters were there?
Three
LaVerne, Maxene and Patty. Their first big hit was 'Bei Mir Bist Du Schön' in 1937.
Q 14The Andrews Sisters introduced 'Boogie Woogie Bugle Boy' in which 1941 Abbott and Costello film?
Q 21Which Cole Porter song was Artie Shaw's breakthrough 1938 recording and best-known hit?
Begin the Beguine
Before it his band had languished for two years; after it he was a major star, and briefly married to both Lana Turner and Ava Gardner.
Q 22Woody Herman's bands were known collectively by what name?
The Herd
His first hit was 'Woodchopper's Ball' in 1939, and Stravinsky wrote the Ebony Concerto for the band in 1945.
Q 23Kay Kyser's popular NBC radio show of 1939-49 combined big band music with what?
A quiz
It was called Kay Kyser's Kollege of Musical Knowledge, and Kyser played the 'Ol' Professor' in cap and gown.
Buck Privates
It reached number six on the pop chart. Bette Midler's 1973 cover and Christina Aguilera's 'Candyman' both pay tribute to it.
Q 15'Rum and Coca-Cola', a 1945 Andrews Sisters hit, was originally a calypso with lyrics by which Trinidadian?
Lord Invader
American comedian Morey Amsterdam copyrighted it in the US as his own, which ended in a lawsuit.
Q 16In August 1942 the American Federation of Musicians struck against record companies over what?
Royalty payments
Union boss James Petrillo banned members from commercial recording for over two years, which is why so many 1943 hits are sung a cappella.
Q 17'Sentimental Journey' (1944), with Les Brown's band, launched which singer?
Doris Day
It became an unofficial homecoming anthem for troops in 1945. She went on to be Hollywood's top box-office star in the early 1960s.
Q 18Which vocal group took the nonsense song 'Mairzy Doats' to number one in March 1944?
The Merry Macs
It was Decca's best-selling record of the year. The words are a garbling of 'mares eat oats'.
Q 19Which clarinetist was known as the 'King of Swing'?
Benny Goodman
His 1938 Carnegie Hall concert is often called jazz's coming-out party to the world of respectable music.
Q 20The 'Sentimental Gentleman of Swing', who employed the young Sinatra, was known for playing which instrument?
Trombone
His biggest hit, 'I'll Never Smile Again', spent 12 weeks at number one in 1940 with Sinatra on vocals.
Q 24'Take the A Train', which became Duke Ellington's theme in 1941, was written by which composer?
Billy Strayhorn
He was originally hired as a lyricist in 1939. The title came from directions Ellington gave him to get to Harlem.
Q 25Which drummer-bandleader's orchestra gave Ella Fitzgerald her start with "A-Tisket, A-Tasket"?
Chick Webb
They were the house band at Harlem's Savoy Ballroom. She led the band herself after his death in 1939.
Q 26Billie Holiday's anti-lynching song "Strange Fruit" was released in 1939 on which label?
Commodore
Columbia refused to record it. The song was written by a Bronx schoolteacher, Abel Meeropol, under the name Lewis Allan.
Q 27Who gave Billie Holiday her nickname 'Lady Day'?
Lester Young
She called him 'Prez' in return. The saxophonist was her closest musical partner.
Q 28Nat King Cole's group, the top-selling act on Capitol Records in the 1940s, was what size of ensemble?
A trio
He started as a jazz pianist. 'Straighten Up and Fly Right' topped the charts in 1944, before he became a solo balladeer.
Q 29According to Mel Tormé, 'The Christmas Song' was written in July 1945 during what?
A hot summer heatwave
He and Robert Wells were trying to think cool. The Nat King Cole Trio first recorded it in June 1946.
Q 30Which sax player, nicknamed 'Bird', was the leading figure of bebop?
Charlie Parker
His recordings with Dizzy Gillespie in 1945, once the recording ban lifted, changed jazz for good.