Think You Know Classic Crooners? Ace This Quiz to Prove It

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Step into the golden age of song—an era defined by smooth vocals, timeless melodies, and voices that turned music into romance. From the 1940s to the ’60s, legendary singers like Sinatra, Crosby, Martin, and Nat King Cole set the standard, filling airwaves with swing, soul, and style that still resonate today. This quiz is your ticket back to smoky lounges and big‑band ballads. Can you match the song to the singer, the collaboration to the crooner, or the story to the star? With 20 questions covering hits, history, and behind‑the‑music moments, only true fans will score high. Ready to show you’ve got the classics down? Let’s see if your music knowledge is truly golden.
1 /20

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

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2 /20

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

3 /20

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

4 /20

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

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5 /20

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

6 /20

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

7 /20

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

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8 /20

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

9 /20

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

10 /20

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

11 /20

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

12 /20

Which singer had the famous song "Mele Kalikimaka"?

13 /20

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

14 /20

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

15 /20

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

16 /20

Which artist made "Smile" a classic in 1954?

17 /20

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

18 /20

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

19 /20

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

20 /20

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

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