120+ Best Oldies Trivia Questions & Answers

Question: The Letterman pop group formed in what year?

Answer: 1959

Question: What was Louis Armstrong's nickname?

Answer: Pops

Question: In which year was Louis Armstrong born?

Answer: 1901

Question: Which of these is a famous song by Frank Sinatra?

Answer: My Way

Question: Which of these songs was a hit for Dean Martin?

Answer: You're Nobody till Somebody Loves You

Question: The song 'Got to Be There' was the debut single of which singer?

Answer: Michael Jackson

Question: Who wrote and released the song 'Please, Please, Please' in 1956?

Answer: James Brown

Question: What was the original name of the singing group The Supremes?

Answer: The Primettes

Question: Who originally sung 'My Heart Belongs to Daddy'?

Answer: Mary Martin

Question: Who famously recorded the song 'Anything Goes' in 1956?

Answer: Frank Sinatra

Question: Which singer released the song 'War' in 1970?

Answer: Edwin Starr

Question: Which singer had the first-ever UK Number One?

Answer: Al Martino

Question: Which artist released the song 'A World Without Love' in 1964?

Answer: Peter and Gordon

Question: Who first recorded the song 'Ain't That a Kick in the Head' in 1960?

Answer: Dean Martin

Question: Which music group recorded the song 'Hey Paula' in 1962?

Answer: Paul & Paula

Question: At what age have several famous musicians died and joined a 'club'?

Answer: 27

Question: Who was the manager of Elvis Presley?

Answer: Colonel Tom Parker

Question: The band Smokey Robinson and the Miracles were also known as what?

Answer: The Miracles

Question: Who famously sung the song 'Stand by Me' in 1961?

Answer: Ben E King

Question: Which of these was a 1958 song by The Champs?

Answer: Tequila

Question: The song 'I Heard It Through the Grapevine' was famously sung by who?

Answer: Marvin Gaye

Question: Which singer released the song 'Spirit in the Sky' in 1969?

Answer: Norman Greenbaum

Question: The song 'Stuck in the Middle with You' features in which of these movies?

Answer: Reservoir Dogs

Question: In what country was Judy Garland born?

Answer: USA

Question: Who released the single 'Katherine' in 1967?

Answer: Ben E King

Question: Which of these is the title of a 1972 album by Aretha Franklin?

Answer: Young, Gifted and Black

Question: Who had a hit with 'Beep Beep' in 1958?

Answer: The Playmates

Question: Dean Martin died in what year?

Answer: 1995

Question: Which band released the song 'Spinning Wheel' in 1969?

Answer: Blood, Sweat & Tears

Question: The song 'The Candy Man' originally appeared in which film?

Answer: Willy Wonka & the Chocolate Factory

Question: The 1940 single 'The End of the Rainbow' was sung by who?

Answer: Judy Garland

Question: Which band reunited for the Live 8 concerts?

Answer: Pink Floyd

Question: Nat King Cole is famous for playing which instrument?

Answer: Piano

Question: Which band released the grunge-pioneering album 'Nevermind'?

Answer: Nirvana

Question: Whose song 'My Heart Will Go On' was the best-selling single of 1997?

Answer: Celine Dion

Question: Which music group released the song 'The Wah-Watusi' in 1962?

Answer: The Orlons

Question: Who wrote and recorded the song 'Call Me'?

Answer: Aretha Franklin

Question: 'Respect' and 'Think' are both songs by which singer?

Answer: Aretha Franklin

Question: 'Green Onions' is the debut album of which music group?

Answer: Booker T. & the M.G.'s

Question: Which member of The Monkees died in 2012?

Answer: Davy Jones

Question: Which group released the song 'Mr. Sandman' in 1954?

Answer: The Chordettes

Question: Which of these is the name of a popular song?

Answer: Wake Up Little Susie

Question: Which music group released the song 'I'll Be There' in 1970?

Answer: Jackson 5

Question: The Elton John song 'Candle in the Wind' was originally about which actress?

Answer: Marilyn Monroe

Question: The song 'That's All Right' was the debut single of which singer?

Answer: Elvis Presley

Question: Elvis Presley was born in which state?

Answer: Mississippi

Question: In 1992, which Whitney Houston song became the best-selling single by a female artist?

Answer: I Will Always Love You

Question: Who wrote the song 'Who Wants to Be a Millionaire'?

Answer: Cole Porter

Question: Which of these is the title of a famous song recorded by Frank Sinatra?

Answer: Moonlight in Vermont

Question: Who composed the song 'God Bless America'?

Answer: Irving Berlin

Question: Cole Porter wrote the songs in which of these musical?

Answer: Kiss Me, Kate

Question: '16 Candles' was a hit for which band?

Answer: The Crests

Question: In 2012, who became the solo artist with the most number one albums?

Answer: Madonna

Question: What instrument is Louis Armstrong famous for playing?

Answer: Trumpet

Question: Who wrote the song 'White Christmas'?

Answer: Irving Berlin

Question: The song 'Land of 1,000 Dances' was a hit for which of these artists?

Answer: Wilson Pickett

Question: What was the title of the album Frank Sinatra released in 1993?

Answer: Duets

Question: 'You're The Top' was famously sung by who?

Answer: Paul Whiteman

Question: Who was Bob Dylan's idol that he traveled to New York City to see?

Answer: Woody Guthrie

Question: Diana Ross and Mary Wilson were founding members of which band?

Answer: The Supremes

Question: How many Grammy Awards did Ella Fitzgerald win?

Answer: 13

Question: Who wrote and released the song 'Hallelujah I Love Her So' in 1956?

Answer: Ray Charles

Question: American singer and songwriter Mort Shuman played which instrument?

Answer: Piano

Question: How many octaves could Ella Fitzgerald's voice span?

Answer: Three

Question: Who won the first episode of the music contest show 'American Idol'?

Answer: Kelly Clarkson

Question: Who founded the American all-female singing group Bluebelles?

Answer: Patti LaBelle

Question: Who was the first to record the song 'Hound Dog'?

Answer: Big Mama Thornton

Question: Who famously recorded the song 'Heebie Jeebies' in 1926?

Answer: Louis Armstrong

Question: Who co-wrote and sung '(Sittin' On) The Dock of the Bay'?

Answer: Otis Redding

Question: Who famously had a hit with the song 'My Heart Belongs to Me'?

Answer: Barbra Streisand

Question: Billie Holiday recorded the song 'Strange Fruit' in which year?

Answer: 1939

Question: Who famously recorded the song 'You Make Me Feel So Young' in 1959?

Answer: Ella Fitzgerald

Question: What type of singing voice did Nat King Cole have?

Answer: Baritone

Question: Cindy Birdsong, a member of The Supremes, was born in which state?

Answer: New Jersey

Question: The album 'Everything Is Everything', released in 1970 was by who?

Answer: Diana Ross

Question: Ben E King released which of these albums in 1965?

Answer: Seven Letters

Question: Blue Christmas' was a hit for Elvis in which year?

Answer: 1964

Question: Who had a hit with the song 'Rhythm of Life' in 1969?

Answer: Sammy Davis, Jr.

Question: In what year was the song 'Night and Day' released?

Answer: 1932

Question: In what year did Phil Harris have a hit with 'The Thing'?

Answer: 1950

Question: In what year did the band The Famous Flames form?

Answer: 1953

Question: In what year did Frank Sinatra release his last album?

Answer: 1994

Question: 'In what year did Frank Sinatra release the album 'My Way'?

Answer: 1969

Question: In 1963, which singer released his first big hit at age 13?

Answer: Stevie Wonder

Question: Billie Holiday recorded the song 'Strange Fruit' in which year?

Answer: 1939

Question: What was the name of the band that Bill Haley had?

Answer: Comets

Question: Who replaced Diana Ross as the lead singer of The Supremes in 1970?

Answer: Jean Terrell

Question: Who founded the American all-female singing group Bluebelles?

Answer: Patti LaBelle

Question: Which girl group was formed to provide backing vocals for Ray Charles?

Answer: The Raelettes

Question: Which punk band won their first and only US gold record in 1994?

Answer: Bad Religion

Question: Which band released the song 'Love Rollercoaster' in 1975?

Answer: Ohio Players

Question: In 2007, the band The Mars Volta released an album in what form?

Answer: USB flash drive

Question: The Vogues released which of these singles in 1969?

Answer: Green Fields

Question: Turn Around, Look at Me' is an album and single by which band?

Answer: The Vogues

Question: Which pop-punk band enjoyed mainstream success with the album 'Enema of the State'?

Answer: Blink-182

Question: Which band had the best-selling album of the 2000s?

Answer: The Beatles

Question: On whose show did The Beatles make their first US TV appearance?

Answer: Ed Sullivan

Question: Which punk band released the album 'Straight Outta Compton'?

Answer: N.W.A.

Question: Which artist released the first British rock and roll single?

Answer: Cliff Richard

Question: How many Gold Records did The Lettermen achieve?

Answer: 11

Question: How many studio albums did Frank Sinatra release?

Answer: 59

Question: In 2008, who set the record for most U.S. number one singles by a solo artist?

Answer: Mariah Care

Question: What was the title of Barbra Streisand's first single?

Answer: Miss Marmelstein

Question: What was the title of Elvis Presley's first single?

Answer: That's All Right

Question: What was the title of Elvis Presley's first album?

Answer: Elvis Presley

Question: Who wrote the song 'Lonely Avenue' that later became a hit for Ray Charles?

Answer: Doc Pomus

Question: Who wrote the lyrics to the song 'Come Fly with Me'?

Answer: Sammy Cahn

Question: Who wrote the song 'Respect' that was originally released by Otis Redding?

Answer: Otis Redding

Question: Who wrote the song 'Who Wants to Be a Millionaire'?

Answer: Cole Porter

Question: Who originally sung 'I Get a Kick Out of You'?

Answer: Ethel Merman

Question: Who wrote the song 'White Christmas'?

Answer: Irving Berlin

Question: Who wrote and released the song 'Call Me'?

Answer: Aretha Franklin

Question: Who wrote the song 'God Bless America'?

Answer: Irving Berlin

Question: Who wrote and released the song 'Please, Please, Please' in 1956?

Answer: James Brown

Question: Who wrote the song 'Hallelujah I Love Her So' that was released by Ray Charles?

Answer: Ray Charles