The Musicians of the 1940s Quiz


By: Olivia Cantor

7 Min Quiz

Image: William P. Gottlieb via Wiki Commons

About This Quiz

The popular music we enjoy today has great roots that we should honor. Without these earlier examples of fine tunes, we would not have many of the finer tunes we enjoy listening to on a daily basis these days. And those earlier tunes were also great works of earlier musicians. Do you think you can pinpoint them out if we give you some clues? Give this a shot and see!

The early decades of the 20th century were very important in the formation of formidable music genres we totally trip on today. Back during the time when R&B was developing as rhythm and blues, jazz was coming into play from specific major areas in the U.S., and rock and roll was slowly being morphed from different musical influences, all other sorts of musicality were falling into place in their respective notches in history. Not only are we talking about songs from great singers, vocal groups, and bands, but we're also talking about legendary composers and musicians who all contributed to the cool happening sounds of the 1940s -- artists who continue to inspire and influence the artists of today.

So, let's see if you can guess who these important musicians are in the list. Put on your musical thinking caps and play on! 

She sang "God Bless The Child" and "Summertime." Who was this great lady who sang the blues?

Billie Holiday is definitely one of the greatest musicians to come out of the great '40s, and her style is being emulated by newer singers even up to now. She had great hits that continue to be appreciated by generations, even up to the present time.


Who was this famous crooner who began his career in the 1940s, and was always linked to Italian organized crime?

Frank Sinatra began his career in the swing era but really hit his stride among the “bobbysoxers” of the 1940s. While his career did stall in the 1950s, this led to him becoming a Las Vegas regular, and a member of the Rat Pack.


Of what type of musical group was Count Basie the leader?

Count Basie was a multi-talented musician known more as a jazz pianist, bandleader, and composer. His jazz orchestra was one of the big groups in the 1940s swing era, and he introduced many innovations on how the orchestra was structured in terms of instruments used. He was also a mentor for entire generations of jazz musicians.


Which memorable singer of the 1940s had the song, “Unforgettable,” as his signature song?

Most people forget that Nat King Cole was not only a brilliant singer, but he was a jazz pianist as well. In fact, his performing trio of musicians became the example others followed in terms of structure and performance. Cole was also very active on Broadway, film, and television in the succeeding decades, and was the first African-American to host a television series.


Ella Fitzgerald was known as “Lady Ella” and the “First Lady of Song.” Of what type of music was she known as the Queen?

Ella Fitzgerald was a uniquely talented interpreter of songs, with hits under her belt like her version of “Over the Rainbow,” “Dream a Little Dream of Me,” and “Cheek to Cheek.” She collaborated with many musicians in her life, notably Louis Armstrong, Duke Ellington, and The Ink Spots, to name a few.


If you’re listening to an old version of “White Christmas,” then chances are, you are listening to this singer who became famous in the 1940s. Who was he?

Bing Crosby was a pioneer in both the way pop music was sung, and how it was recorded. He took full advantage of the way a singer could almost whisper into a microphone, rather than use an exaggerated stage style. He was also instrumental in developing recording technology behind the scenes.


Dinah Shore is famous for being one of the earlier interpreters of this now-controversial Christmas song. What was the name of the song?

Dinah Shore became famous in the big band era of the 1940s, and she did it with a solo career, rather than being connected to a group. That being said, she was said to have failed singing auditions while trying to get into the orchestras of Benny Goodman and Jimmy Dorsey.


Louis Armstrong may be known for his gravelly singing voice, but what was his musical instrument?

Louis Armstrong’s signature song, “What a Wonderful World,” is uniquely identifiable because of his voice. If you want to hear more of his signature musical style, however, it’s a good idea to listen to his other songs, such as “Hello, Dolly,” and “Jeepers Creepers.”


What was the name of this George Gershwin song about infatuation, sung by Sarah Vaughan?

Sarah Vaughan may have been a jazz singer, but her vocal stylings have been said to have operatic tinges. Her low, sultry voice has influenced the likes of Anita Baker, Sade, and Dianne Reeves.


One of Glenn Miller’s most famous songs was about getting you into this. What was the song?

Many of the stars of the Swing era were not the singers themselves, but the orchestra leaders, like Glenn Miller. What made Glenn Miller somewhat unusual was that his chosen musical instrument was a trombone, whereas many orchestra leaders were usually pianists.


Were the Andrews Sisters really sisters?

The Andrews Sisters were a singing group famous for their very close and intricate harmonies. They consisted of the actual sisters, Maxene, Patty, and Laverne. Their most famous song, “Boogie Woogie Bugle Boy,” is considered an early form of rhythm and blues.


This 1946 song from crooner Perry Como describes him as a prisoner of this. What is “this?”

Perry Como was known for the apparent ease with which he sang in a crooning style. He was also a pioneer in the development of weekly musical variety shows. It’s been said that his total success from these media crossovers is unmatched by anyone in his time.


What was patriotic singer Jo Stafford known as when she was an entertainer for the troops?

Jo Stafford first became famous as a member of The Pied Pipers, who provided background voices to the likes of Tommy Dorsey and Frank Sinatra. She, along with Perry Como, also participated in the first commercial radio broadcast from a plane.


Cab Calloway was singing about a girl hooked on drugs in this famous early song of his. What was the song?

Cab Calloway’s career reached its peak in the 1940s, where he appeared in Porky Pig cartoons, movies like “Stormy Weather,” and even had his own gossip column in a magazine. He also published a dictionary for jive (slang based on Jazz and the Harlem area).


Eartha Kitt was a talented singer who could sing in more than one language. What was the other language that she used in many of her songs?

Eartha Kitt became famous in the 1940s as a member of the Katherine Dunham Company, a modern dance group composed wholly of African-Americans. A 2013 biography claimed that her father was Caucasian, which may have explained her light complexion, but this has been contested.


What song did patriotic composer Irving Berlin write, which became practically a national anthem during World War II?

Irving Berlin became famous in the 1940s for composing practically an entire songbook of patriotic songs to support the war efforts. When the war was over, he wrote other kinds of songs, like “There’s No Business Like Show Business.”


"Anything Goes" for this talented composer, who is "Easy to Love" if you're willing to "Experiment." Who was this talented guy?

Cole Porter was already a prolific songwriter before the 1940s, but it was his way of using his material in musicals and movies in the 1940s that made him such a big name during that decade. He was also famous for being gay at a time when it was not talked about, though he did follow social conventions.


In 1944, Jimmy Dorsey’s orchestra backed Kitty Kallen for this famous Mexican song about being too passionate. What song was this?

Jimmy Dorsey’s orchestra was no stranger to having hits sung in other languages, as they also had one with “Amapola,” a Spanish-language song. Jimmy Dorsey also wrote many songs, including the jazz standard, “I’m Glad There is You.”


What was 1940s' bebop pioneer Charlie Parker’s preferred musical instrument?

Charlie “Bird” Parker’s career was one about breaking stereotypes in the jazz world. His early bebop work had him playing with the likes of Dizzy Gillespie and Thelonious Monk. His compositions often required that the performing musicians had to be very skilled.


In the ‘40s, Frank Sinatra briefly became a featured vocalist of a popular orchestra led by this man. Who was this bandleader?

Harry James was a musician who used the trumpet and had his own orchestra, with hits like “You Made Me Love You (I Didn’t Want To Do It).” This bandleader was also once married to pin-up beauty Betty Grable during the ‘40s.


Benny Goodman was known as the King. But what was he the King of?

Benny Goodman was a pivotal figure in jazz, as one of his concerts became a key performance for jazz to go into the mainstream. During the 1940s, he went into bebop, but afterward returned to swing, and then explored classical music.


Sammy Kaye’s signature song was about a special set of lights. What were these lights?

Sammy Kaye was a bandleader and songwriter who favored the “sweet” sound for his big band. Some critics and fellow contemporaries loved to make fun of his preferred sound. In 1941, Sammy Kaye and his orchestra also recorded “Remember Pearl Harbor.”


Dizzy Gillespie helped develop this style of jazz. What was it called?

Dizzy Gillespie, already a famous trumpet player in the 1940s, helped develop the earliest form of Latin jazz called Afro-Cuban jazz. It mixed syncopated Cuban rhythmic styles with jazz harmonies and improvisation. Dizzy co-wrote “Manteca,” one of the early defining songs of this genre.


There were many saxophonists who were bandleaders, but for what kind of saxophone was Freddy Martin known?

Freddy Martin and his orchestra were admired by jazz musicians, but he didn’t see himself as a jazz player. He preferred the “sweet” sound for his big band, and was known as one of the most musical and melodic among them.


The Mills Brothers had a big hit in the 1940s with “Paper Doll.” What was the song about?

The Mills Brothers had, at the beginning of the 1940s, found success in Europe, but their fame back home was at an all-time low. “Paper Doll” was the B-side to “I’ll Be Around,” but it became the bigger hit. The song may talk about paper dolls, but only in the sense that they’re better than people who can leave you behind.


Vaughn Monroe was the first to record this ode to winter weather and Christmas. What was that song?

Vaughn Monroe was notable as a dashing and manly baritone singer and bandleader in the 1940s. He also owned a club called The Meadows, which became his band’s home base. For most of the decade, he had regular radio and TV shows, though he wasn’t too convinced about building a career in the movies.


“Take the A Train” became the signature theme of Duke Ellington’s orchestra in the 1940s. Where was the train going?

Duke Ellington and his orchestra were said to be in an experimental stage in the 1940s. The band had amazing musicians, and Ellington himself was figuring out how to go past the traditional three minutes limit for a song. Some of Ellington’s efforts were praised by critics, but in general, it was not a successful musical direction.


Tommy Dorsey was known for the great people in his band, but how did he get all these talented people?

Tommy Dorsey was not only the leader of a big band, he was also one of the most successful musicians in the business side of things in the 1940s. His keen eye for talent netted him Frank Sinatra, who would record around 80 songs with him.


Hank Williams was a big star again by the end of the 1940s, but what problem stalled his career in the beginning?

Hank Williams was a country musician who had had a good start in the latter part of the 1930s, but by the early part of the 1940s, was saddled with alcoholism. He eventually climbed out of the bottle, and by the end of the decade, was part of the Grand Ole Opry.


Roy Rogers was another man who was known as the King in the 1940s. What was he the King of?

Roy Rogers was a musical giant in the country scene, but what sealed his legacy was that he was also popular on the movie screen and on television. He and his wife, Dale Evans, were advocates for adoption, and they had many adopted children.


He got "Georgia on My Mind" during "The Right Time," yeah, "What'd I Say?" Who was this musical prodigy?

Ray Charles had been working hard to get to a position where he could be noticed nationally, all throughout the 1940s. In 1949, he had a national hit, “Confession Blues.” This would be the beginning of his real climb to the top of the music world.


Gene Autry was so popular that he had rules that reflected his do-good personality. What was the name of these rules?

Gene Autry was aware of his influence as a musician, an actor, and a television star. To this end, he created the Cowboy Code composed of ten rules to abide by that children could follow to be better people.


Multi-talented Eddie Cantor was a versatile musician, but his greatest musical creation is a TV theme song. What kind of TV show was it?

Eddie Cantor was an all-in-one entertainer, who in the 1940s kept the tradition of follies, vaudeville, and upbeat comedy music alive. He also co-wrote the theme song to the “Merrie Melodies” cartoon show, which featured Bugs Bunny. It was known as “Merrily We Roll Along.”


What made the Ink Spots unusual in some of the places where they played?

The Ink Spots were unusual for the 1940s in that they contributed to breaking down the race barriers in music by performing in Southern venues where African-Americans normally couldn’t even step foot in. Their biggest chart topper was “The Gypsy,” a record released in 1946.


Who was Dean Martin’s performance partner in the 1940s?

Dean Martin and Jerry Lewis started out as solo acts, but their friendship made them try a dual act. Basically, the idea was that Dean Martin would try to be the straight musical front man, while Jerry Lewis would create comedic chaos around him. It worked, for a few years.


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