Oldies Music Trivia
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107 free Oldies Music trivia questions with answers — music quiz, new questions added Oct 2026.
Oldies radio has a fairly precise meaning: the pop, rock and roll, doo-wop, soul and surf music of roughly 1955 to 1969, the records that KOOL-FM in Phoenix and a wave of imitators built a format around in the early 1970s. This quiz sticks to that golden window and to the songs that still get played, from Rock Around the Clock to Sugar, Sugar. The 58 oldies music trivia questions here go beyond naming the artist. You will be asked why the FBI spent 31 months listening to Louie Louie, which single hit number one twice in separate chart runs, who gave up his seat on Buddy Holly's plane, what Phil Spector printed on a record label to fool disc jockeys, how much Motown was started with, and which cartoon band had the biggest hit of 1969. Easy questions come first; the back half is for people who know their B-sides. No lyrics are quoted, so nothing here will get you humming the answer. Every fact is checked against the Wikipedia article for that song, artist or event, and the sentence that establishes it is shown under each question.
30 of 107 questions with answers and explanations. Play the quiz
Q 01Which New Orleans pianist had 1950s hits with 'Ain't That a Shame' and 'Blueberry Hill'?
Fats Domino
Fats Domino never had a number one pop hit, even though Pat Boone's milder cover of 'Ain't That a Shame' went to number one in 1955.
Q 02Which 1973 film is often credited with kick-starting a wave of 1950s nostalgia?
American Graffiti
American Graffiti was made for under $800,000, yet it became one of the most profitable films of all time.
Q 03Which group's 'Rock Around the Clock' spent eight weeks at number one in 1955?
Bill Haley & His Comets
Bill Haley & His Comets squeezed it into the last half hour of the session, because the producer insisted they record 'Thirteen Women' first.
Q 04Which 1955 film's opening credits turned 'Rock Around the Clock' into a hit a year after the record came out?
Blackboard Jungle
Blackboard Jungle had teenagers dancing in the aisles, and the single was re-released on the back of the film's success.
Q 05'Rock Around the Clock' opened which 1970s sitcom during its first two seasons?
Happy Days
Happy Days helped send the 1954 original back onto the US charts in 1974.
Q 06In which Mississippi town was Elvis Presley born in 1935?
Tupelo
Tupelo Hardware is where Elvis got his first guitar at 11, after his mother talked him out of a rifle, or in some tellings a bicycle.
Q 07Elvis Presley's three competitive Grammy wins all came for which kind of recordings?
Gospel
Gospel shaped his teens, and for How Great Thou Art, his first Grammy winner, he recorded with the Imperials, led by his early influence Jake Hess.
Q 08Which Graceland room did Elvis Presley turn into a recording studio in 1976?
Jungle Room
The Jungle Room hosted his last studio sessions, and songs from them came out on Moody Blue weeks before his death in 1977.
Q 09On Elvis Presley's third Ed Sullivan Show appearance, in January 1957, how did the cameras frame him?
Only from the waist up
Only from the waist up that night, though legend often pins that framing on his first Sullivan appearance, where he was shown head-to-toe.
Q 10In which US state did the 1959 plane crash that killed Buddy Holly, Ritchie Valens and the Big Bopper happen?
Iowa
Iowa is where Holly, fed up with the tour's freezing buses, chartered a small plane after their Clear Lake show; it crashed minutes after takeoff.
Q 11Which future country star gave up his seat on Buddy Holly's doomed 1959 flight to the Big Bopper, who had the flu?
Waylon Jennings
Waylon Jennings had jokingly told Holly he hoped his plane would crash, a remark that haunted him for years after the deaths.
Q 12How did Ritchie Valens win a seat on Buddy Holly's plane?
A coin toss with guitarist Tommy Allsup
A coin toss with guitarist Tommy Allsup went Valens's way, and Allsup later named his club Tommy's Heads Up Saloon after it.
Q 13Which 1971 song named the Buddy Holly plane crash 'The Day the Music Died'?
'American Pie' by Don McLean
Q 21Which Portland, Oregon, band's 1963 recording of 'Louie Louie' reached number two on the Billboard Hot 100?
The Kingsmen
The Kingsmen beat rivals Paul Revere & the Raiders, who cut it soon after in the same Portland studio with Columbia behind them yet stalled outside the Hot 100.
Q 22What did the FBI conclude about the 'Louie Louie' lyrics?
Unintelligible
Unintelligible, the FBI lab decided, so after 31 months the bureau could not find the record obscene and brought no charges.
Q 23Who is credited with writing 'Respect' and recorded it first, in 1965, two years before Aretha Franklin's hit?
Otis Redding
Otis Redding sang it as a man demanding respect at home, but Aretha Franklin's gender-flipped 1967 remake became a feminist anthem.
'American Pie' by Don McLean grew out of the morning the 13-year-old learned of the crash while delivering newspapers.
Q 14'La Bamba', Ritchie Valens' 1958 hit, is a folk song from which Mexican state on the Gulf Coast?
Veracruz
Veracruz weddings are where it is traditionally danced, with the couple using their feet to tie a ribbon into a bow as a symbol of their union.
Q 15Valens' 'La Bamba' was originally released as the B-side of which single?
'Donna'
'Donna' was the A-side, yet its flip, 'La Bamba', charted too and became the most enduring hit of Valens's short career.
Q 16Which band's cover of 'La Bamba' reached number one on the Hot 100 in 1987?
Los Lobos
Los Lobos recorded it for the 1987 Ritchie Valens biopic, and it became the first song sung in Spanish to top the Hot 100.
Q 17'Johnny B. Goode' is one of 27 pieces of music carried on what, launched in 1977?
The Voyager Golden Record
The Voyager Golden Record team argued over it: folklorist Alan Lomax called Chuck Berry's music adolescent, and Carl Sagan replied that Earth has plenty of adolescents.
Q 18At which studio did Jerry Lee Lewis record 'Great Balls of Fire' in October 1957?
Sun Studio in Memphis
Sun Studio in Memphis sent the record to number one on the country and UK charts, but within a year news that Lewis had married his 13-year-old cousin stalled his career.
Q 19Which 1986 film has 'Great Balls of Fire' pounded out on a bar piano?
Top Gun
Top Gun gave the song to Goose, and the 2022 sequel echoed the scene with his son Rooster, played by Miles Teller, singing it at a bar piano.
Q 20What was Chubby Checker's 'The Twist' the first Hot 100 record to do?
Reach number one in two runs
Grown-ups took up the twist in late 1961, letting the record reach number one in two runs, in 1960 and again in 1962.
Q 24What was '(Sittin' On) The Dock of the Bay' the first Billboard Hot 100 record to be?
A posthumous number one
Its singer's manager had thought the song too pop, yet it became a posthumous number one just over three months after his death.
Q 25Which future Blues Brothers band member co-wrote '(Sittin' On) The Dock of the Bay' with its singer?
Steve Cropper
Steve Cropper helped finish it, building on the first verse its singer had written while staying on Bill Graham's houseboat in Sausalito.
Q 26'Be My Baby' was the 1963 debut single of which group on Philles Records?
The Ronettes
The Ronettes had just one member on the record, Ronnie Spector, while a young Cher sang among the backing vocalists.
Q 27Which Beach Boy has called 'Be My Baby' the greatest pop record ever made?
Brian Wilson
Brian Wilson answered it with the Beach Boys' 1964 hit 'Don't Worry Baby', which borrowed its groove.
Q 28Which doo-wop group took 'The Lion Sleeps Tonight' to number one on the Hot 100 in 1961?
The Tokens
The Tokens' hit gave no credit to Solomon Linda, the Zulu singer who wrote the original, and he died in poverty in 1962.
Q 29Pete Seeger was in which folk group when he recorded 'Wimoweh', his version of 'Mbube'?
The Weavers
The Weavers' 'Wimoweh' took its title from Pete Seeger's mishearing of the Zulu chorus 'uyimbube'.
Q 30'Mack the Knife' comes from which 1928 stage work?
The Threepenny Opera
The Threepenny Opera gained it only days before the 1928 Berlin premiere, as a last-minute number to introduce its ruthless antihero, Macheath.