1940s Music Trivia
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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
Best-selling single of all time, at an estimated 50 million copies: the 1942 master was so damaged by heavy use that Crosby had to re-record the song in 1947, and that remake is the version usually heard today.
Q 02Which songwriter wrote 'White Christmas' for the 1942 film Holiday Inn?
Irving Berlin
Irving Berlin was presenting the Best Song Oscar at the 1943 ceremony when he opened the envelope and had to read out his own name as the winner.
Q 03Glenn Miller received the first ever gold record in 1942 for a song about a train to which city?
Chattanooga
Chattanooga Choo Choo had sold about 1.2 million copies, so in February 1942 Miller's record label marked the feat by handing him a gold copy of the disc during a broadcast.
Q 04Which tune was Glenn Miller's theme song?
Moonlight Serenade
Moonlight Serenade was a tune Miller composed while studying with the music theorist Joseph Schillinger, and his band was using it as its theme before it even had that title.
Q 05Glenn Miller went missing in December 1944 when his plane vanished over which body of water?
The English Channel
The English Channel was where an Army inquiry concluded his small plane went down, blaming weather, mechanical failure and human error; Miller was flying to Paris ahead of his Army band, and no wreckage was ever found.
Q 06Which Glenn Miller hit took its famous riff from 'Tar Paper Stomp', a 1930 record by trumpeter Wingy Manone?
In the Mood
In the Mood was arranged by Joe Garland around the riff; because Manone had never written his tune down and registered it, copyright law of the day left other musicians free to borrow it.
Q 07Frank Sinatra left Harry James's band after less than a year to sing with which bandleader?
Tommy Dorsey
Tommy Dorsey kept him for two years, and the pair cut some eighty records together before Sinatra walked out in 1942 to go solo.
Q 08What were the teenage girls who mobbed Frank Sinatra in the early 1940s called?
Bobby soxers
Bobby soxers showed the music business that teenagers were a market of their own; until then pop records had been made mainly for adults.
Q 09What name was given to the chaos when thousands of Sinatra fans were shut out of the Paramount Theatre in October 1944?
The Columbus Day Riot
The Columbus Day Riot took its name from the public holiday on 12 October 1944: with schools closed, girls began queuing at midnight and thousands more swarmed Times Square.
Q 10Which nickname of Frank Sinatra's is in the title of his 1946 debut album?
The Voice
The Voice of Frank Sinatra topped the album chart; he retired in the early 1970s but came back in 1973 with an album titled Ol' Blue Eyes Is Back.
Q 11Bing Crosby won the Academy Award for Best Actor for which 1944 film?
Going My Way
Going My Way also made Oscar history: co-star Barry Fitzgerald was nominated as both Best Actor and Best Supporting Actor for the same role, and the Academy changed its rules so that could not happen again.
Q 12Which Bing Crosby hit began as a Montana poet's verse?
Don't Fence Me In
Don't Fence Me In began as a poem by Robert Fletcher, a Montana engineer; Cole Porter bought it in 1934 and was credited alone when it became a hit ten years later, and Fletcher's name was added only afterwards.
Q 13The Andrews Sisters sang 'Don't Sit Under' which tree?
Apple
Q 21Which Cole Porter song was Artie Shaw's breakthrough 1938 recording and best-known hit?
Begin the Beguine
Begin the Beguine was issued as a B-side because his label doubted so long a tune would sell; instead it lifted Shaw's band out of two years of obscurity and made him a star.
Q 22Woody Herman's bands were known collectively by what name?
The Herd
The Herd commissioned a piece from Igor Stravinsky: his Ebony Concerto, which the band premiered at Carnegie Hall in 1946 even though Herman found his own solo part frighteningly hard.
Q 23Kay Kyser's hit NBC radio show of the 1940s combined big band music with what?
A quiz
A quiz: the Kollege of Musical Knowledge made Kyser a star, but after entertaining troops in the war he resolved to give up performing for money, and in 1950 he walked away from show business for good.
The apple tree stood for a promise: the lyric is a pledge between two lovers to stay faithful while one is away at war, and the sisters sang it on screen in a 1942 film.
Q 14The Andrews Sisters introduced 'Boogie Woogie Bugle Boy' in which 1941 Abbott and Costello film?
Buck Privates
Buck Privates earned the song an Oscar nomination, and three decades later Bette Midler's cover carried it back into the American top ten.
Q 15Which 1945 Andrews Sisters number one began as a Trinidadian calypso with lyrics by Lord Invader?
Rum and Coca-Cola
Rum and Coca-Cola was credited in the US to comedian Morey Amsterdam, who had visited Trinidad while it was a local hit; Lord Invader sued and won damages, though Amsterdam kept the copyright.
Q 16In August 1942 the American Federation of Musicians struck against record companies over what?
Royalty payments
Royalty payments were the union's demand: its boss James Petrillo barred members from making records, so labels cut their 1943 hits with singers backed only by vocal groups.
Q 17'Sentimental Journey', a wartime hit with Les Brown's band, launched which singer?
Doris Day
Doris Day's first number one came out just as the war in Europe was ending, and it became an unofficial homecoming anthem for returning servicemen.
Q 18Which wartime nonsense song gave the vocal group the Merry Macs a number one hit in 1944?
Mairzy Doats
Mairzy Doats only sounds like gibberish: sung slowly the title becomes 'mares eat oats', and co-writer Milton Drake said his small daughter's garbled nursery rhyme gave him the idea.
Q 19Which clarinetist was known as the 'King of Swing'?
Benny Goodman
Benny Goodman won the crown after a 1935 tour that had been flopping: at the Palomar Ballroom in Los Angeles the crowd went wild for his hot arrangements, a night often called the start of the swing era.
Q 20Tommy Dorsey, billed as the 'Sentimental Gentleman of Swing', was famous for playing which instrument?
Trombone
Trombone: his smooth tone on it earned him the nickname, though he had started out on trumpet, taught by his bandleader father, before switching.
Q 24'Take the A Train', which became Duke Ellington's theme in 1941, was written by which composer?
Billy Strayhorn
Billy Strayhorn took the title from the subway directions Ellington sent him for reaching his Harlem home, then threw his draft away; Ellington's son recalled fishing it out of the bin.
Q 25Which drummer-bandleader's orchestra gave Ella Fitzgerald her start with "A-Tisket, A-Tasket"?
Chick Webb
Chick Webb's orchestra was the house band at Harlem's Savoy Ballroom, and when he died in 1939 Fitzgerald took over as its leader for three years.
Q 26Which Billie Holiday protest song did her own label decline to record?
Strange Fruit
Strange Fruit went instead to the tiny Commodore label, which her friend Milt Gabler ran from his Manhattan record shop; Holiday called it her biggest-selling record.
Q 27Who gave Billie Holiday her nickname 'Lady Day'?
Lester Young
Lester Young got a title in return: Holiday called him 'Prez', her president of the saxophone, and for a while he lodged with her and her mother.
Q 28Nat King Cole first found fame in the 1940s leading what size of group from the piano?
A trio
A trio of piano, guitar and bass: its 1944 hit 'Straighten Up and Fly Right' retold a folk tale that Cole's preacher father had used in a sermon.
Q 29Which holiday standard, first recorded by Nat King Cole, did Mel Tormé co-write during a 1945 summer heatwave?
The Christmas Song
The Christmas Song began, by Tormé's account, as four wintry lines his partner Bob Wells jotted down to cool himself off; Tormé spotted them on the piano and about forty minutes later the song was done.
Q 30Which sax player, nicknamed 'Bird', was the leading figure of bebop?
Charlie Parker
Charlie Parker and his fellow modernists worked the style out in after-hours Harlem jam sessions during the 1942-44 recording ban, so the birth of bebop went largely unrecorded.