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Classic Pop Music Trivia for Seniors: Questions and Answers

Reliving some of your favorite classic pop songs can be a great way to engage with your friends, bring back memories, and have fun. Gather up your fellow senior citizens, grab some snacks and drinks (no alcohol required!), put on your nostalgia caps, and let’s get quizzing!

The ‘40s and ‘50s

The group who performed Rock Around the Clock was named Bill Haley and…

The Comets

Who made the song I’m Dreaming of a White Christmas famous?

Bing Crosby

What jazz singer and trumpeter is known for the song What a Wonderful World?

Louis Armstrong

What was the stage name of the musician born as Ernest Evans?

Chubby Checker


What singer turned actor is known as Old Blue Eyes?

Frank Sinatra

Who was known as The King of Rock and Roll?

Elvis Presley

What was jazz bandleader Benny Goodman’s nickname?

The King of Swing

What country star was known as The Man in Black?

Johnny Cash

Duets, trios and quartets

What brothers were known for hits like Wake Up Little Susie, Bye-Bye Love and All I Have to Do Is Dream?

The Everly Brothers

What trio performed Puff the Magic Dragon?

Peter, Paul, and Mary

What Liverpool rock-and-roll quartet took the world by storm in the 60s and what were its four members’ names?

The Beatles; John Lennon, Paul McCartney, Ringo Starr and George Harrison

One-hit wonders

What was the hit song by the one-hit wonder The Tokens?

The Lion Sleeps Tonight

What Halloween smash was by one-hit wonder Bobby “Boris” Pickett and the Crypt-Kickers?

Monster Mash

What one-hit wonder played the surfing hit Wipe Out?

The Surfaris

Musical places

What hotel can you check out from at anytime, but never leave?

Hotel California

What rock ‘n roll legend is known as The Boss, and what state does he famously hail from?

Bruce Springsteen, from New Jersey

What state does the devil go down to in the famous Charlie Daniels song?

The Devil Went Down to Georgia

Where was the singer Israel Kaʻanoʻi Kamakawiwoʻole, popularly known as Iz, from?


In what city was John Lennon assassinated?

New York City

Instruments and instrumentalists

Which three guitar legends were, at different times, members of The Yardbirds?

Eric Clapton, Jimmy Page and Jeff Beck

What instrument does Stevie Wonder play?

The piano

What heavy metal band has a one-armed drummer and what is his name?

Def Leppard’s drummer Rick Allen

Rock and Roll legends

Who is the lead singer of The Rolling Stones?

Mick Jagger

What are the names of the five musical legends who later teamed up to form The Traveling Wilburys?

Roy Orbison, Tom Petty, Jeff Lynne, George Harrison, and Bob Dylan

Movies and shows

What Doris Day song was first introduced in the 1956 Alfred Hitchcock film The Man Who Knew Too Much?

Que Sera Sera

Who performed the famous song and dance in Singing in the Rain?

Gene Kelly

In their famous dancing duo, who was Fred Astaire’s partner?

Ginger Rogers

What two actors played the romantic male and female lead in the film Dirty Dancing?

Patrick Swayze and Jennifer Gray

What award-winning 1961 movie musical told the sad story of two star-crossed lovers on opposite sides of a gang war, and what Shakespeare play was it based on?

West Side Story; Romeo & Juliet

What are the names of the unlikely romantic couple played by John Travolta and Olivia Newton-John in the movie musical Grease?

Danny and Sandy

What legendary diva also starred in non-musical films like Nuts, Yentl and The Prince of Tides?

Barbra Streisand

What acclaimed Broadway musical was based on an 1862 Victor Hugo novel about the French Revolution?

Les Misérables


What hit song by the heavy metal band Aerosmith featured the rappers Run-DMC?

Walk This Way

What song recorded to benefit the charity U.S.A. for Africa was performed by a chorus of 46 famous musicians including Michael Jackson, Lionel Richie, Kenny Rogers, Cyndi Lauper, Willie Nelson, Tina Turner and the Pointer Sisters?

We Are the World

What was the name of Elton John’s long-time song writing partner?

Bernie Taupin

Independence comes in many forms, and independent living at Winchester Gardens honors them all. Discover a relaxed and enriching retirement lifestyle in Northern New Jersey.

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