Don’t Call Yourself a Classic Music Lover Until You Ace This Crooner Challenge

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Step back in time to the golden era of smooth vocals and timeless melodies with this ultimate crooner quiz! From the 1940s to the 1960s, these legendary male singers defined an age of romance, swing, and heartfelt ballads that still echo in our hearts today. Think of smoky lounges, big band orchestras, and voices that could melt butter—icons like Frank Sinatra, Bing Crosby, Dean Martin, and Nat King Cole ruled the airwaves with hits that became cultural staples. Whether it's holiday classics, love anthems, or jazzy tunes that make you sway, these crooners captured the essence of mid-20th-century America and beyond. Their music influenced generations, from Rat Pack glamour to modern covers by artists like Michael Bublé. This challenge tests your knowledge of their signature songs, collaborations, and legacies. With 40 questions, each featuring four options, you'll uncover fascinating facts about these velvet-voiced legends. Are you a true aficionado, or just humming along? Dive in and prove your classic music creds—ace it, and you'll earn bragging rights as a certified crooner connoisseur!
1 /40

Which artist wrote and recorded one of his greatest hits "Lonely Boy" for his film work?

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2 /40

Who made "It's Not for Me to Say" timeless and performed it in the 1957 movie Lizzie?

3 /40

Which singer had the double compilation album "The Impossible Dream" which focused exclusively on covers of songs?

4 /40

Who recorded the self-penned "Dream Lover" in 1959?

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5 /40

Which singer made "For the Good Times" a #1 hit single?

6 /40

Who made "Round and Round" a big hit for RCA Victor on January 15, 1957?

7 /40

Which artist recorded "Nature Boy" in 1948?

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8 /40

Who had the song "Memories Are Made of This"?

9 /40

Which singer recorded "Pennies from Heaven" topped the charts for ten weeks in 1936?

10 /40

Who crooned "I've Got You Under My Skin" in 1946 on his weekly radio show?

11 /40

Which singer wrote the theme for The Tonight Show Starring Johnny Carson?

12 /40

Who sang the famous "Wonderful! Wonderful!" in late 1956?

13 /40

Which singer performed 1944 hit record "Swinging on a Star" with Bing Crosby?

14 /40

Whose career finally took off in 1958 when he recorded "Splish Splash"?

15 /40

Which artist signed with Columbia Records and had his first number-one popular song with "Because of You" in 1951?

16 /40

Who was nicknamed as "Mr. C."?

17 /40

Which crooner's final studio album was titled L-O-V-E?

18 /40

Whose song "Volare" reached number 15 in the U.S. and number 2 in the UK?

19 /40

Which singer had the famous song "Mele Kalikimaka"?

20 /40

Who crooned "Strangers in the Night" and reached No. 1 on both the Billboard Hot 100 chart and the Easy Listening chart?

21 /40

Which artist recorded "Diana" which was one of the best selling singles ever by a Canadian recording artist?

22 /40

Who had been inducted into the Grammy Hall of Fame for "Misty" in 2002?

23 /40

Which singer re-recorded "Can't Take My Eyes Off You" as a duet with British actress and singer Denise van Outen in 2003?

24 /40

Who performed "Beyond the Sea", a jazzy English-language version of Charles Trenet's French hit song "La Mer"?

25 /40

Which crooner is famous for "Rags to Riches" in early 1953?

26 /40

Who recorded "Papa Loves Mambo" with Mitchell Ayres's orchestra?

27 /40

Which artist made "Smile" a classic in 1954?

28 /40

Who performed "Ain't That a Kick in the Head" in Ocean's 11?

29 /40

Which singer performed "White Christmas" and topped the Billboard chart for 11 weeks?

30 /40

Who covered "Theme from New York, New York" (often abbreviated to just "New York, New York") in 1980?

31 /40

Which singer wrote the hit "Put Your Head on My Shoulder"?

32 /40

Who released his second single "Chances Are" in 1957?

33 /40

Which artist sang "Moon River", the theme from Breakfast at Tiffany's at the 1962 Academy Awards?

34 /40

Who won a Record of the Year for "Mack the Knife"?

35 /40

Which singer recorded his signature song "I Left My Heart in San Francisco" in 1962?

36 /40

Who made the "Catch a Falling Star" famous in late 1957?

37 /40

Which crooner sang "Mona Lisa" (No. 1 song of 1950)?

38 /40

Who made "Everybody Loves Somebody" a hit and knocked the Beatles' "A Hard Day's Night" off number one?

39 /40

Which singer sang the Academy Award-winning song "Swinging on a Star"?

40 /40

Who crooned the iconic "Fly Me to the Moon" in 1964?

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