1. Billie Holiday
   Sarah Vaughan
2. Nina Simone
   Ella Fitzgerald

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.

1. Tony Bennett
   Bing Crosby
2. Frank Sinatra
   Perry Como

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.

1. Quintet
   Orchestra
2. Trio
   Quartet

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.

1. Cab Calloway
   Slim Gaillard
2. Fats Waller
   Nat King Cole

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.

1. Jazz
   Swing
2. Bebop
   Country

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.

1. Buddy Clark
   Dick Powell
2. Bing Crosby
   Jerry Wayne

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.

1. Santa Baby
   Baby, it’s Cold Outside
2. Jingle Bells
   Winter Wonderland

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.

1. Saxophone
   Drums
2. Piano
   Trumpet

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.”

1. The Man I love
   Embraceable You
2. I’ve Got a Crush on You
   Someone to Watch Over Me

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.

1. Kalamazoo
   In the Mood
2. Moonlight Serenade
   Fools Rush In

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.

1. Yes
   No
2. Some were
   Only by marriage

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.

1. Hate
   Destiny
2. Desire
   Love

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.

1. Sergeant Stafford
   G.I. Jo
2. Ms. Iron Lungs
   Miss American Jo

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.

1. Junker’s Blues
   Who put the Benzedrine in Mrs. Murphy's Ovaltine?
2. Minnie the Moocher
   The Reefer 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).

1. French
   Arabic
2. Chinese
   Swahili

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.

1. Let’s Go West Again
   God Bless America
2. How About a Cheer for the Navy
   American Eagles

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.”

1. Cole Porter
   Tex Ritter
2. Roy Milton
   George Formby

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.

1. La Cucaracha
   Perfidia
2. El Rancho Grande
   Besame Mucho

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.”

1. Saxophone
   Flute
2. Trombone
   Piano

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.

1. Johnny Mathis
   Buddy Clark
2. Harry James
   Dean Martin

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.

1. Jazz
   Ballroom
2. Pop
   Swing

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.

1. Christmas lights
   Harbor lights
2. Runway lights
   Highway 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.”

1. Calypso
   Bebop
2. Afro-Cuban
   Progressive

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.

1. Soprano saxophone
   Alto saxophone
2. Baritone sax
   Tenor sax

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.

1. A girl thinking of her wedding day
   A man jilted by his girlfriend for another
2. It’s literally about paper dolls.
   True love

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.

1. Deck The Halls
   Santa Baby
2. Let it Snow, Let it Snow, Let it Snow
   Jingle Bells

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.

1. New Orleans
   Detroit
2. Chicago
   Harlem

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.

1. He got them from other big bands.
   He trained them.
2. He looked at amateur performers.
   He put ads out in the papers.

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.

1. Divorce
   Alcoholism
2. Nervous breakdown
   Family tragedy

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.

1. Ballads
   Dance
2. Country
   Jazz

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.

1. Willie Johnson
   Stevie Wonder
2. George Shearing
   Ray Charles

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.

1. The Ten Commandments
   The Cowboy Code
2. The Gentleman’s Rules
   Good manners and Right Conduct

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.

1. A soap opera show
   A Western show
2. A cartoon show
   A late night talk show

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.”

1. They were African-American
   They were very tall
2. They had no orchestra
   They were not patriotic

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.

1. Tony Bennett
   Sammy Davis Jr.
2. Frank Sinatra
   Jerry Lewis

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.